active listing constraint for bidding

send messages to winners / losers of an auction
add listing expiry checker task
2025-09-10 23:51:01 +00:00 · 2025-09-10 03:53:48 +00:00 · 2025-09-10 03:15:58 +00:00 · 2025-09-09 02:45:56 +00:00 · 2025-09-09 01:40:36 +00:00 · 2025-09-05 22:48:17 +00:00
61 changed files with 6381 additions and 2797 deletions
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -121,7 +121,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0f50776554130342de4836ba542aa85a4ddb361690d7e8df13774d7284c3d5c2"
 dependencies = [
 "include_dir",
- "itertools",
+ "itertools 0.10.5",
 "proc-macro-error2",
 "proc-macro2",
 "quote",
@@ -134,6 +134,17 @@ version = "0.7.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "7c02d123df017efcdfbd739ef81735b36c5ba83ec3c59c80a9d7ecc718f92e50"

+[[package]]
+name = "async-trait"
+version = "0.1.89"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9035ad2d096bed7955a320ee7e2230574d28fd3c3a0f186cbea1ff3c7eed5dbb"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.106",
+]
+
 [[package]]
 name = "atoi"
 version = "2.0.0"
@@ -518,6 +529,12 @@ version = "0.15.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "1aaf95b3e5c8f23aa320147307562d361db0ae0d51242340f558153b4eb2439b"

+[[package]]
+name = "downcast"
+version = "0.11.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1435fa1053d8b2fbbe9be7e97eca7f33d37b28409959813daefc1446a14247f1"
+
 [[package]]
 name = "dptree"
 version = "0.5.1"
@@ -543,6 +560,15 @@ dependencies = [
 "serde",
 ]

+[[package]]
+name = "encoding_rs"
+version = "0.8.35"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "75030f3c4f45dafd7586dd6780965a8c7e8e285a5ecb86713e63a79c5b2766f3"
+dependencies = [
+ "cfg-if",
+]
+
 [[package]]
 name = "env_filter"
 version = "0.1.3"
@@ -667,6 +693,12 @@ dependencies = [
 "percent-encoding",
 ]

+[[package]]
+name = "fragile"
+version = "2.0.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "28dd6caf6059519a65843af8fe2a3ae298b14b80179855aeb4adc2c1934ee619"
+
 [[package]]
 name = "funty"
 version = "2.0.0"
@@ -824,6 +856,25 @@ version = "0.3.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0cc23270f6e1808e30a928bdc84dea0b9b4136a8bc82338574f23baf47bbd280"

+[[package]]
+name = "h2"
+version = "0.4.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f3c0b69cfcb4e1b9f1bf2f53f95f766e4661169728ec61cd3fe5a0166f2d1386"
+dependencies = [
+ "atomic-waker",
+ "bytes",
+ "fnv",
+ "futures-core",
+ "futures-sink",
+ "http",
+ "indexmap 2.11.0",
+ "slab",
+ "tokio",
+ "tokio-util",
+ "tracing",
+]
+
 [[package]]
 name = "hashbrown"
 version = "0.12.3"
@@ -942,6 +993,7 @@ dependencies = [
 "bytes",
 "futures-channel",
 "futures-core",
+ "h2",
 "http",
 "http-body",
 "httparse",
@@ -953,6 +1005,22 @@ dependencies = [
 "want",
 ]

+[[package]]
+name = "hyper-rustls"
+version = "0.27.7"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e3c93eb611681b207e1fe55d5a71ecf91572ec8a6705cdb6857f7d8d5242cf58"
+dependencies = [
+ "http",
+ "hyper",
+ "hyper-util",
+ "rustls",
+ "rustls-pki-types",
+ "tokio",
+ "tokio-rustls",
+ "tower-service",
+]
+
 [[package]]
 name = "hyper-tls"
 version = "0.6.0"
@@ -988,9 +1056,11 @@ dependencies = [
 "percent-encoding",
 "pin-project-lite",
 "socket2",
+ "system-configuration",
 "tokio",
 "tower-service",
 "tracing",
+ "windows-registry",
 ]

 [[package]]
@@ -1213,6 +1283,15 @@ dependencies = [
 "either",
 ]

+[[package]]
+name = "itertools"
+version = "0.14.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2b192c782037fadd9cfa75548310488aabdbf3d2da73885b31bd0abd03351285"
+dependencies = [
+ "either",
+]
+
 [[package]]
 name = "itoa"
 version = "1.0.15"
@@ -1376,6 +1455,32 @@ dependencies = [
 "windows-sys 0.59.0",
 ]

+[[package]]
+name = "mockall"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "39a6bfcc6c8c7eed5ee98b9c3e33adc726054389233e201c95dab2d41a3839d2"
+dependencies = [
+ "cfg-if",
+ "downcast",
+ "fragile",
+ "mockall_derive",
+ "predicates",
+ "predicates-tree",
+]
+
+[[package]]
+name = "mockall_derive"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "25ca3004c2efe9011bd4e461bd8256445052b9615405b4f7ea43fc8ca5c20898"
+dependencies = [
+ "cfg-if",
+ "proc-macro2",
+ "quote",
+ "syn 2.0.106",
+]
+
 [[package]]
 name = "native-tls"
 version = "0.2.14"
@@ -1584,26 +1689,42 @@ dependencies = [
 "windows-targets 0.52.6",
 ]

+[[package]]
+name = "paste"
+version = "1.0.15"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "57c0d7b74b563b49d38dae00a0c37d4d6de9b432382b2892f0574ddcae73fd0a"
+
 [[package]]
 name = "pawctioneer-bot"
 version = "0.1.0"
 dependencies = [
 "anyhow",
+ "async-trait",
+ "base64",
 "chrono",
 "dotenvy",
+ "dptree",
 "env_logger",
 "futures",
+ "itertools 0.14.0",
 "lazy_static",
 "log",
+ "mockall",
 "num",
+ "paste",
+ "regex",
+ "reqwest",
 "rstest",
 "rust_decimal",
+ "seq-macro",
 "serde",
 "sqlx",
 "teloxide",
 "teloxide-core",
 "thiserror",
 "tokio",
+ "uuid",
 ]

 [[package]]
@@ -1719,6 +1840,32 @@ dependencies = [
 "zerocopy",
 ]

+[[package]]
+name = "predicates"
+version = "3.1.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a5d19ee57562043d37e82899fade9a22ebab7be9cef5026b07fda9cdd4293573"
+dependencies = [
+ "anstyle",
+ "predicates-core",
+]
+
+[[package]]
+name = "predicates-core"
+version = "1.0.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "727e462b119fe9c93fd0eb1429a5f7647394014cf3c04ab2c0350eeb09095ffa"
+
+[[package]]
+name = "predicates-tree"
+version = "1.0.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "72dd2d6d381dfb73a193c7fca536518d7caee39fc8503f74e7dc0be0531b425c"
+dependencies = [
+ "predicates-core",
+ "termtree",
+]
+
 [[package]]
 name = "proc-macro-crate"
 version = "3.3.0"
@@ -1928,16 +2075,20 @@ checksum = "d429f34c8092b2d42c7c93cec323bb4adeb7c67698f70839adec842ec10c7ceb"
 dependencies = [
 "base64",
 "bytes",
+ "encoding_rs",
 "futures-core",
 "futures-util",
+ "h2",
 "http",
 "http-body",
 "http-body-util",
 "hyper",
+ "hyper-rustls",
 "hyper-tls",
 "hyper-util",
 "js-sys",
 "log",
+ "mime",
 "mime_guess",
 "native-tls",
 "percent-encoding",
@@ -2225,6 +2376,12 @@ version = "1.0.26"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "56e6fa9c48d24d85fb3de5ad847117517440f6beceb7798af16b4a87d616b8d0"

+[[package]]
+name = "seq-macro"
+version = "0.3.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1bc711410fbe7399f390ca1c3b60ad0f53f80e95c5eb935e52268a0e2cd49acc"
+
 [[package]]
 name = "serde"
 version = "1.0.219"
@@ -2679,6 +2836,27 @@ dependencies = [
 "syn 2.0.106",
 ]

+[[package]]
+name = "system-configuration"
+version = "0.6.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3c879d448e9d986b661742763247d3693ed13609438cf3d006f51f5368a5ba6b"
+dependencies = [
+ "bitflags",
+ "core-foundation",
+ "system-configuration-sys",
+]
+
+[[package]]
+name = "system-configuration-sys"
+version = "0.6.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8e1d1b10ced5ca923a1fcb8d03e96b8d3268065d724548c0211415ff6ac6bac4"
+dependencies = [
+ "core-foundation-sys",
+ "libc",
+]
+
 [[package]]
 name = "take_mut"
 version = "0.2.2"
@@ -2780,6 +2958,12 @@ dependencies = [
 "windows-sys 0.60.2",
 ]

+[[package]]
+name = "termtree"
+version = "0.5.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8f50febec83f5ee1df3015341d8bd429f2d1cc62bcba7ea2076759d315084683"
+
 [[package]]
 name = "thiserror"
 version = "2.0.16"
@@ -2896,6 +3080,16 @@ dependencies = [
 "tokio",
 ]

+[[package]]
+name = "tokio-rustls"
+version = "0.26.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8e727b36a1a0e8b74c376ac2211e40c2c8af09fb4013c60d910495810f008e9b"
+dependencies = [
+ "rustls",
+ "tokio",
+]
+
 [[package]]
 name = "tokio-stream"
 version = "0.1.17"
@@ -3097,9 +3291,9 @@ checksum = "06abde3611657adf66d383f00b093d7faecc7fa57071cce2578660c9f1010821"

 [[package]]
 name = "uuid"
-version = "1.18.0"
+version = "1.18.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f33196643e165781c20a5ead5582283a7dacbb87855d867fbc2df3f81eddc1be"
+checksum = "2f87b8aa10b915a06587d0dec516c282ff295b475d94abf425d62b57710070a2"
 dependencies = [
 "getrandom 0.3.3",
 "js-sys",
@@ -3311,6 +3505,17 @@ version = "0.1.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "5e6ad25900d524eaabdbbb96d20b4311e1e7ae1699af4fb28c17ae66c80d798a"

+[[package]]
+name = "windows-registry"
+version = "0.5.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5b8a9ed28765efc97bbc954883f4e6796c33a06546ebafacbabee9696967499e"
+dependencies = [
+ "windows-link",
+ "windows-result",
+ "windows-strings",
+]
+
 [[package]]
 name = "windows-result"
 version = "0.3.4"
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -4,6 +4,7 @@ version = "0.1.0"
 edition = "2021"

 [dependencies]
+serde = { version = "1.0.219" }
 teloxide = { version = "0.17.0", features = ["macros", "ctrlc_handler"] }
 tokio = { version = "1.0", features = ["macros", "rt-multi-thread"] }
 sqlx = { version = "0.8.6", features = [
@@ -14,17 +15,26 @@ sqlx = { version = "0.8.6", features = [
    "rust_decimal",
 ] }
 rust_decimal = { version = "1.33" }
-chrono = { version = "0.4" }
+chrono = { version = "0.4", features = ["serde"] }
 log = "0.4"
 env_logger = "0.11.8"
 anyhow = "1.0"
 dotenvy = "0.15"
 lazy_static = "1.4"
-serde = "1.0.219"
 futures = "0.3.31"
 thiserror = "2.0.16"
 teloxide-core = "0.13.0"
 num = "0.4.3"
+itertools = "0.14.0"
+async-trait = "0.1"
+regex = "1.11.2"
+paste = "1.0"
+dptree = "0.5.1"
+seq-macro = "0.3.6"
+base64 = "0.22.1"
+mockall = "0.13.1"
+reqwest = "0.12.23"
+uuid = "1.18.1"

 [dev-dependencies]
 rstest = "0.26.1"
--- a/migrations/20240827001_initial_schema.sql
+++ b/migrations/20240827001_initial_schema.sql
@@ -9,12 +9,16 @@ CREATE TABLE users (
    id INTEGER PRIMARY KEY,
    telegram_id INTEGER UNIQUE NOT NULL,
    username TEXT,
-    display_name TEXT,
+    first_name TEXT,
+    last_name TEXT,
    is_banned INTEGER DEFAULT 0,
    created_at TEXT DEFAULT CURRENT_TIMESTAMP,
    updated_at TEXT DEFAULT CURRENT_TIMESTAMP
 ) STRICT;

+CREATE INDEX idx_users_telegram_id ON users(telegram_id);
+CREATE INDEX idx_users_username ON users(username);
+
 -- Main listing table (handles all listing types)
 CREATE TABLE listings (
    id INTEGER PRIMARY KEY,
@@ -22,6 +26,7 @@ CREATE TABLE listings (
    listing_type TEXT NOT NULL, -- 'basic_auction', 'multi_slot_auction', 'fixed_price_listing', 'blind_auction'
    title TEXT NOT NULL,
    description TEXT,
+    currency_type TEXT NOT NULL, -- 'usd'

    -- Pricing (stored as INTEGER cents for USD)
    starting_bid INTEGER,
@@ -32,6 +37,7 @@ CREATE TABLE listings (
    slots_available INTEGER DEFAULT 1,

    -- Timing
+    is_active INTEGER DEFAULT 1,
    starts_at TEXT DEFAULT CURRENT_TIMESTAMP,
    ends_at TEXT NOT NULL,
    anti_snipe_minutes INTEGER DEFAULT 5,
@@ -41,6 +47,10 @@ CREATE TABLE listings (
    FOREIGN KEY (seller_id) REFERENCES users(id)
 ) STRICT;

+CREATE INDEX idx_listings_seller_id ON listings(seller_id);
+CREATE INDEX idx_listings_type ON listings(listing_type);
+CREATE INDEX idx_listings_ends_at ON listings(ends_at);
+
 -- Proxy bid strategies (NOT actual bids, but bidding strategies)
 CREATE TABLE proxy_bids (
    id INTEGER PRIMARY KEY,
@@ -57,6 +67,8 @@ CREATE TABLE proxy_bids (
    UNIQUE(listing_id, buyer_id) -- One active proxy per user per listing
 ) STRICT;

+CREATE INDEX idx_proxy_bids_listing_buyer ON proxy_bids(listing_id, buyer_id);
+
 -- Actual bids that happened (events)
 CREATE TABLE bids (
    id INTEGER PRIMARY KEY,
@@ -81,6 +93,10 @@ CREATE TABLE bids (
    FOREIGN KEY (proxy_bid_id) REFERENCES proxy_bids(id)
 ) STRICT;

+CREATE INDEX idx_bids_listing_id ON bids(listing_id);
+CREATE INDEX idx_bids_buyer_id ON bids(buyer_id);
+CREATE INDEX idx_bids_amount ON bids(bid_amount);
+
 -- Media attachments
 CREATE TABLE listing_medias (
    id INTEGER PRIMARY KEY,
@@ -93,6 +109,8 @@ CREATE TABLE listing_medias (
    FOREIGN KEY (listing_id) REFERENCES listings(id)
 ) STRICT;

+CREATE INDEX idx_listing_medias_listing_id ON listing_medias(listing_id);
+
 -- User preferences
 CREATE TABLE user_settings (
    user_id INTEGER PRIMARY KEY,
@@ -104,12 +122,19 @@ CREATE TABLE user_settings (
    FOREIGN KEY (user_id) REFERENCES users(id)
 ) STRICT;

-- Create indexes for better performance
-CREATE INDEX idx_listings_seller_id ON listings(seller_id);
-CREATE INDEX idx_listings_type ON listings(listing_type);
-CREATE INDEX idx_listings_ends_at ON listings(ends_at);
-CREATE INDEX idx_bids_listing_id ON bids(listing_id);
-CREATE INDEX idx_bids_buyer_id ON bids(buyer_id);
-CREATE INDEX idx_bids_amount ON bids(bid_amount);
-CREATE INDEX idx_proxy_bids_listing_buyer ON proxy_bids(listing_id, buyer_id);
-CREATE INDEX idx_listing_medias_listing_id ON listing_medias(listing_id);
+-- Message about a listing that were forwarded from the bot to a channel or user
+CREATE TABLE forwarded_listings (
+    id INTEGER PRIMARY KEY,
+    listing_id INTEGER NOT NULL,
+    telegram_message_id INTEGER NOT NULL,
+    telegram_chat_id INTEGER NOT NULL,
+    forwarding_user_id INTEGER NOT NULL,
+    created_at TEXT DEFAULT CURRENT_TIMESTAMP,
+    updated_at TEXT DEFAULT CURRENT_TIMESTAMP,
+
+    FOREIGN KEY (listing_id) REFERENCES listings(id),
+    FOREIGN KEY (forwarding_user_id) REFERENCES users(id)
+) STRICT;
+
+CREATE INDEX idx_forwarded_listings_listing_id ON forwarded_listings(listing_id);
+CREATE INDEX idx_forwarded_listings_forwarding_user_id ON forwarded_listings(forwarding_user_id);
--- a/migrations/02_add_bid_active_listing_constraint.sql
+++ b/migrations/02_add_bid_active_listing_constraint.sql
@@ -0,0 +1,15 @@
+-- Add constraint to prevent bids on inactive listings
+-- This ensures atomicity at the database level
+
+-- Create a trigger to prevent bids on inactive listings
+-- This is more reliable than CHECK constraints in SQLite
+CREATE TRIGGER prevent_bid_on_inactive_listing
+    BEFORE INSERT ON bids
+    FOR EACH ROW
+    WHEN (
+        SELECT COALESCE(is_active, 0) FROM listings WHERE id = NEW.listing_id
+    ) != 1
+BEGIN
+    SELECT RAISE(ABORT, 'Cannot place bid on inactive listing');
+END;
+
--- a/src/bidding/confirm_bid_amount_callback.rs
+++ b/src/bidding/confirm_bid_amount_callback.rs
@@ -0,0 +1,336 @@
+use crate::{
+    bidding::BiddingState,
+    commands::new_listing::validations::{validate_price, SetFieldError},
+    db::{bid::NewBid, listing::PersistedListing, user::PersistedUser, MoneyAmount},
+    message::MessageType,
+    App, BotError, BotResult, RootDialogue,
+};
+use anyhow::{anyhow, Context};
+use chrono::Utc;
+use itertools::Itertools;
+use log::{error, info};
+use teloxide::types::*;
+
+pub async fn handle_awaiting_bid_amount_input(
+    app: App,
+    listing: PersistedListing,
+    dialogue: RootDialogue,
+    msg: Message,
+) -> BotResult {
+    // parse the bid amount into a MoneyAmount
+    let text = msg
+        .text()
+        .ok_or(BotError::user_visible("Please enter a valid bid amount"))?;
+    let bid_amount = match validate_price(text) {
+        Ok(bid_amount) => bid_amount,
+        Err(SetFieldError::ValidationFailed(e)) => {
+            return Err(BotError::user_visible(e));
+        }
+        Err(other) => {
+            return Err(anyhow!("Error validating bid amount: {other:?}").into());
+        }
+    };
+
+    let bid_amount_str = format!("{}", bid_amount.with_type(listing.base.currency_type));
+    app.bot
+        .send_html_message(
+            format!("Confirm bid amount: {bid_amount_str} - this cannot be undone!"),
+            Some(InlineKeyboardMarkup::default().append_row([
+                InlineKeyboardButton::callback(
+                    format!("Confirm bid amount: {bid_amount_str}"),
+                    "confirm_bid",
+                ),
+                InlineKeyboardButton::callback("Cancel", "cancel_bid"),
+            ])),
+        )
+        .await?;
+
+    dialogue
+        .update(BiddingState::AwaitingConfirmBidAmount(
+            listing.persisted.id,
+            bid_amount,
+        ))
+        .await
+        .context("failed to update dialogue")?;
+
+    Ok(())
+}
+
+pub async fn handle_awaiting_confirm_bid_amount_callback(
+    app: App,
+    buyer: PersistedUser,
+    listing: PersistedListing,
+    bid_amount: MoneyAmount,
+    dialogue: RootDialogue,
+    callback_query: CallbackQuery,
+) -> BotResult {
+    let callback_data = callback_query
+        .data
+        .as_deref()
+        .ok_or(BotError::user_visible("Missing data in callback query"))?;
+
+    let bid_amount = match callback_data {
+        "confirm_bid" => bid_amount,
+        "cancel_bid" => {
+            dialogue.exit().await.context("failed to exit dialogue")?;
+            app.bot
+                .send_html_message("Bid cancelled".to_string(), None)
+                .await?;
+            return Ok(());
+        }
+        _ => {
+            return Err(BotError::user_visible(format!(
+                "Invalid response {callback_data}"
+            )))
+        }
+    };
+
+    if listing.base.ends_at < Utc::now() {
+        return app
+            .send_message(MessageType::BidInvalidListingExpired { listing, buyer })
+            .await;
+    }
+
+    let bid = NewBid::new_basic(listing.persisted.id, buyer.persisted.id, bid_amount);
+    let bid = app.daos.bid.insert_bid(&bid).await?;
+    dialogue.exit().await.context("failed to exit dialogue")?;
+
+    app.send_message(MessageType::BidHasBeenConfirmedForBuyer {
+        listing: listing.clone(),
+        bid: bid.clone(),
+    })
+    .await?;
+
+    let other_bidder_ids = app
+        .daos
+        .bid
+        .bidder_ids_for_listing(listing.persisted.id)
+        .await?
+        .into_iter()
+        .filter(|id| *id != buyer.persisted.id)
+        .unique();
+
+    for buyer in app.daos.user.where_in_ids(other_bidder_ids).await? {
+        info!("Sending outbid message to {buyer:?}");
+        app.send_message(MessageType::UserHasBeenOutbidForBuyer {
+            listing: listing.clone(),
+            buyer,
+        })
+        .await?;
+    }
+
+    if let Some(seller) = app.daos.user.find_by_id(listing.base.seller_id).await? {
+        app.send_message(MessageType::BidHasBeenPlacedForSeller {
+            listing,
+            buyer,
+            seller,
+            bid,
+        })
+        .await?;
+    } else {
+        error!("Seller not found for listing {listing:?}");
+    }
+
+    Ok(())
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::{db::DAOs, message_sender::MockMessageSender, test_utils::*};
+    use chrono::{Duration, Utc};
+    use dptree::{
+        deps,
+        di::{DependencyMap, Injectable},
+    };
+    use mockall::predicate::function;
+    use std::str::FromStr;
+
+    struct Fixtures {
+        deps: DependencyMap,
+        seller: PersistedUser,
+        buyer: PersistedUser,
+        prev_buyer: PersistedUser,
+        listing: PersistedListing,
+    }
+    async fn set_up_fixtures() -> Fixtures {
+        let Deps { deps, .. } = create_deps().await;
+        let seller = with_test_user(&deps, |seller| {
+            seller.username = Some("seller".to_string());
+            seller.telegram_id = 123.into()
+        })
+        .await;
+        let buyer = with_test_user(&deps, |buyer| {
+            buyer.username = Some("buyer".to_string());
+            buyer.telegram_id = 456.into()
+        })
+        .await;
+        let prev_buyer = with_test_user(&deps, |buyer| {
+            buyer.username = Some("prev_buyer".to_string());
+            buyer.telegram_id = 789.into()
+        })
+        .await;
+        let listing = with_test_listing(&deps, &seller, |_| {}).await;
+        Fixtures {
+            deps,
+            seller,
+            buyer,
+            prev_buyer,
+            listing,
+        }
+    }
+
+    #[tokio::test]
+    async fn test_confirm_bid_with_expired_listing() {
+        let Fixtures {
+            deps,
+            buyer,
+            mut listing,
+            ..
+        } = set_up_fixtures().await;
+
+        // listing has already expired
+        listing.base.ends_at = Utc::now() - Duration::days(1);
+        let listing = deps
+            .get::<DAOs>()
+            .listing
+            .update_listing(&listing)
+            .await
+            .unwrap();
+
+        let cb_query = create_tele_callback_query(
+            "confirm_bid",
+            create_tele_user(|user| user.id = buyer.telegram_id.into()),
+        );
+
+        let mut message_sender = MockMessageSender::new();
+        {
+            let l = listing.clone();
+            let b = buyer.clone();
+            message_sender
+                .expect_send_message()
+                .once()
+                .with(function(move |m| match m {
+                    MessageType::BidInvalidListingExpired { listing, buyer } => {
+                        assert_eq!(listing, &l);
+                        assert_eq!(buyer, &b);
+                        true
+                    }
+                    _ => false,
+                }))
+                .returning(|_| Ok(()));
+        }
+        let deps = with_message_sender(deps, message_sender).await;
+
+        let mut deps = with_dialogue(deps, &buyer).await;
+        deps.insert_container(deps![
+            listing,
+            cb_query,
+            buyer,
+            MoneyAmount::from_str("100.00").unwrap()
+        ]);
+        let ret = handle_awaiting_confirm_bid_amount_callback.inject(&deps)().await;
+        assert!(ret.is_ok(), "{ret:?}");
+    }
+
+    #[tokio::test]
+    async fn test_confirm_bid_amount() {
+        let Fixtures {
+            deps,
+            seller,
+            buyer,
+            prev_buyer,
+            listing,
+        } = set_up_fixtures().await;
+
+        deps.get::<DAOs>()
+            .bid
+            .insert_bid(&NewBid::new_basic(
+                listing.persisted.id,
+                prev_buyer.persisted.id,
+                MoneyAmount::from_str("50.00").unwrap(),
+            ))
+            .await
+            .unwrap();
+
+        let mut message_sender = MockMessageSender::new();
+
+        {
+            let l = listing.clone();
+            let b = buyer.clone();
+            message_sender
+                .expect_send_message()
+                .once()
+                .with(function(move |m| match m {
+                    MessageType::BidHasBeenConfirmedForBuyer { listing, bid, .. } => {
+                        assert_eq!(listing, &l);
+                        assert_eq!(bid.buyer_id, b.persisted.id);
+                        assert_eq!(bid.bid_amount.cents(), 10_000);
+                        assert_eq!(bid.listing_id, l.persisted.id);
+                        true
+                    }
+                    _ => false,
+                }))
+                .returning(|_| Ok(()));
+        }
+
+        {
+            let l = listing.clone();
+            let b = buyer.clone();
+            let s = seller.clone();
+            message_sender
+                .expect_send_message()
+                .once()
+                .with(function(move |m| match m {
+                    MessageType::BidHasBeenPlacedForSeller {
+                        listing,
+                        buyer,
+                        seller,
+                        bid,
+                    } => {
+                        assert_eq!(listing, &l);
+                        assert_eq!(buyer, &b);
+                        assert_eq!(seller, &s);
+                        assert_eq!(bid.buyer_id, b.persisted.id);
+                        assert_eq!(bid.bid_amount.cents(), 10_000);
+                        assert_eq!(bid.listing_id, l.persisted.id);
+                        true
+                    }
+                    _ => false,
+                }))
+                .returning(|_| Ok(()));
+        }
+
+        {
+            let l = listing.clone();
+            let pb = prev_buyer.clone();
+            message_sender
+                .expect_send_message()
+                .once()
+                .with(function(move |m| match m {
+                    MessageType::UserHasBeenOutbidForBuyer { listing, buyer } => {
+                        assert_eq!(listing, &l);
+                        assert_eq!(buyer, &pb);
+                        true
+                    }
+                    _ => false,
+                }))
+                .returning(|_| Ok(()));
+        }
+
+        let deps = with_message_sender(deps, message_sender).await;
+        let cb_query = create_tele_callback_query(
+            "confirm_bid",
+            create_tele_user(|user| user.id = buyer.telegram_id.into()),
+        );
+        let mut deps = with_dialogue(deps, &buyer).await;
+        deps.insert_container(deps![
+            listing,
+            cb_query,
+            buyer,
+            MoneyAmount::from_str("100.00").unwrap()
+        ]);
+        let ret = handle_awaiting_confirm_bid_amount_callback.inject(&deps)().await;
+        assert!(ret.is_ok(), "{ret:?}");
+    }
+}
--- a/src/bidding/keyboards.rs
+++ b/src/bidding/keyboards.rs
@@ -0,0 +1 @@
+
--- a/src/bidding/mod.rs
+++ b/src/bidding/mod.rs
@@ -0,0 +1,189 @@
+mod confirm_bid_amount_callback;
+mod keyboards;
+
+use crate::{
+    bidding::confirm_bid_amount_callback::{
+        handle_awaiting_bid_amount_input, handle_awaiting_confirm_bid_amount_callback,
+    },
+    case,
+    db::{
+        listing::{ListingFields, PersistedListing},
+        user::PersistedUser,
+        DbListingId, DbUserId, MoneyAmount, UserDAO,
+    },
+    dptree_utils::MapTwo,
+    handle_error::with_error_handler,
+    handler_utils::find_listing_by_id,
+    message_utils::user_name_or_link,
+    start_command_data::StartCommandData,
+    App, BotError, BotHandler, BotResult, DialogueRootState, RootDialogue,
+};
+use anyhow::Context;
+use log::info;
+use serde::{Deserialize, Serialize};
+use std::collections::HashMap;
+use teloxide::{
+    dispatching::UpdateFilterExt,
+    types::{InlineKeyboardButton, InlineKeyboardMarkup, Update},
+};
+
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub enum BiddingState {
+    AwaitingBidAmount(DbListingId),
+    AwaitingConfirmBidAmount(DbListingId, MoneyAmount),
+}
+impl From<BiddingState> for DialogueRootState {
+    fn from(state: BiddingState) -> Self {
+        DialogueRootState::Bidding(state)
+    }
+}
+
+pub fn bidding_handler() -> BotHandler {
+    dptree::entry()
+        .branch(
+            Update::filter_message()
+                .filter_map(StartCommandData::get_from_update)
+                .filter_map(StartCommandData::get_place_bid_on_listing_start_command)
+                .branch(
+                    dptree::entry()
+                        .filter_map_async(find_listing_by_id)
+                        .endpoint(with_error_handler(handle_place_bid_on_listing)),
+                ),
+        )
+        .branch(
+            Update::filter_callback_query()
+                .filter_map(StartCommandData::get_from_callback_query)
+                .filter_map(StartCommandData::get_view_listing_bids_start_command)
+                .filter_map_async(find_listing_by_id)
+                .endpoint(with_error_handler(handle_view_listing_bids)),
+        )
+        .branch(
+            Update::filter_message()
+                .chain(case![DialogueRootState::Bidding(
+                    BiddingState::AwaitingBidAmount(listing_id)
+                )])
+                .filter_map_async(find_listing_by_id)
+                .endpoint(with_error_handler(handle_awaiting_bid_amount_input)),
+        )
+        .branch(
+            Update::filter_callback_query()
+                .chain(case![DialogueRootState::Bidding(
+                    BiddingState::AwaitingConfirmBidAmount(listing_id, bid_amount)
+                )])
+                .map2(|(listing_id, bid_amount): (DbListingId, MoneyAmount)| {
+                    (listing_id, bid_amount)
+                })
+                .filter_map_async(async |listing_dao, listing_id| {
+                    find_listing_by_id(listing_dao, listing_id).await
+                })
+                .endpoint(with_error_handler(
+                    handle_awaiting_confirm_bid_amount_callback,
+                )),
+        )
+}
+
+async fn handle_place_bid_on_listing(
+    app: App,
+    user_dao: UserDAO,
+    user: PersistedUser,
+    listing: PersistedListing,
+    dialogue: RootDialogue,
+) -> BotResult {
+    info!("Handling place bid on listing for listing {listing:?} for user {user:?}");
+    let seller = user_dao
+        .find_by_id(listing.base.seller_id)
+        .await?
+        .ok_or(BotError::UserVisibleError("Seller not found".to_string()))?;
+
+    let basic_auction_fields = match &listing.fields {
+        ListingFields::BasicAuction(fields) => fields,
+        _ => {
+            return Err(BotError::UserVisibleError(
+                "Unsupported listing type".to_string(),
+            ))
+        }
+    };
+
+    dialogue
+        .update(BiddingState::AwaitingBidAmount(listing.persisted.id))
+        .await
+        .context("failed to update dialogue")?;
+
+    let mut response_lines = vec![];
+    response_lines.push(format!(
+        "Placing a bid <b>{title}</b>, ran by {seller}",
+        title = listing.base.title,
+        seller = user_name_or_link(&seller)
+    ));
+    let currency_type = listing.base.currency_type;
+    response_lines.push(format!("You are bidding on this listing as: {user:?}"));
+    response_lines.push(format!(
+        "Minimum bid: {}",
+        basic_auction_fields.min_increment.with_type(currency_type)
+    ));
+
+    let keyboard = InlineKeyboardMarkup::default()
+        .append_row([InlineKeyboardButton::callback("Bid $1", "cancel")]);
+
+    app.bot
+        .send_html_message(response_lines.join("\n"), Some(keyboard))
+        .await?;
+
+    Ok(())
+}
+
+async fn handle_view_listing_bids(
+    app: App,
+    listing: PersistedListing,
+    user: PersistedUser,
+) -> BotResult {
+    if listing.base.seller_id != user.persisted.id {
+        return Err(BotError::user_visible(
+            "You are not the seller of this listing",
+        ));
+    }
+    let currency_type = listing.base.currency_type;
+
+    let bids = app.daos.bid.bids_for_listing(listing.persisted.id).await?;
+
+    let mut response_lines = vec![];
+    response_lines.push(format!(
+        "🔍 <b>Bids on <i>{title}</i></b>",
+        title = listing.base.title
+    ));
+
+    let bidding_users = app
+        .daos
+        .user
+        .where_in_ids(bids.iter().map(|bid| bid.buyer_id))
+        .await?
+        .into_iter()
+        .map(|bid| (bid.persisted.id, bid))
+        .collect::<HashMap<DbUserId, PersistedUser>>();
+
+    if let Some(current_bid) = bids.first() {
+        let buyer = bidding_users
+            .get(&current_bid.buyer_id)
+            .ok_or(BotError::internal_str("Buyer not found"))?;
+        response_lines.push(format!(
+            "💰 Current highest bid: <b>{current_bid}</b> from {buyer_name}",
+            current_bid = current_bid.bid_amount.with_type(currency_type),
+            buyer_name = user_name_or_link(buyer)
+        ));
+    } else {
+        response_lines.push("💰 No bids yet".to_string());
+    }
+
+    for bid in bids.iter() {
+        let bidder = bidding_users
+            .get(&bid.buyer_id)
+            .ok_or(BotError::internal_str("Bidder not found"))?;
+        response_lines.push(format!(
+            "💰 Bid: <b>{bid_amount}</b> from {buyer_name}",
+            bid_amount = bid.bid_amount.with_type(currency_type),
+            buyer_name = user_name_or_link(bidder)
+        ));
+    }
+
+    Ok(())
+}
--- a/src/bot_message_sender.rs
+++ b/src/bot_message_sender.rs
@@ -0,0 +1,296 @@
+use anyhow::Context;
+use async_trait::async_trait;
+use teloxide::{
+    payloads::{EditMessageTextSetters, SendMessageSetters},
+    prelude::Requester,
+    types::*,
+    Bot,
+};
+
+use crate::{
+    db::{bid::PersistedBid, listing::PersistedListing, user::PersistedUser},
+    message::MessageType,
+    message_sender::{BoxedMessageSender, MessageSender},
+    message_utils::user_name_or_link,
+    start_command_data::StartCommandData,
+    BotError, BotResult, MessageTarget,
+};
+
+pub struct BotMessageSender(Bot, Option<MessageTarget>);
+impl BotMessageSender {
+    pub fn new(bot: Bot, message_target: Option<MessageTarget>) -> Self {
+        Self(bot, message_target)
+    }
+}
+
+#[async_trait]
+impl MessageSender for BotMessageSender {
+    fn with_target(&self, target: MessageTarget) -> BoxedMessageSender {
+        let clone = Self(self.0.clone(), Some(target));
+        Box::new(clone)
+    }
+    async fn send_html_message(
+        &self,
+        text: String,
+        keyboard: Option<InlineKeyboardMarkup>,
+    ) -> BotResult {
+        let target = self
+            .1
+            .clone()
+            .ok_or(BotError::internal_str("No message target"))?;
+        if let Some(message_id) = target.message_id {
+            log::info!("Editing message in chat: {target:?}");
+            let mut message = self
+                .0
+                .edit_message_text(target.chat_id, message_id, &text)
+                .parse_mode(ParseMode::Html);
+            if let Some(kb) = keyboard {
+                message = message.reply_markup(kb);
+            }
+            message.await.context("failed to edit message")?;
+        } else {
+            log::info!("Sending message to chat: {target:?}");
+            let mut message = self
+                .0
+                .send_message(target.chat_id, &text)
+                .parse_mode(ParseMode::Html);
+            if let Some(kb) = keyboard {
+                message = message.reply_markup(kb);
+            }
+            message.await.context("failed to send message")?;
+        }
+        Ok(())
+    }
+
+    async fn answer_inline_query(
+        &self,
+        inline_query_id: InlineQueryId,
+        results: Vec<InlineQueryResult>,
+    ) -> BotResult {
+        self.0
+            .answer_inline_query(inline_query_id, results)
+            .await
+            .map(|_| ())
+            .map_err(|err| BotError::InternalError(err.into()))
+    }
+
+    async fn answer_callback_query(&self, query_id: CallbackQueryId) -> BotResult {
+        self.0
+            .answer_callback_query(query_id)
+            .await
+            .map(|_| ())
+            .map_err(|err| BotError::InternalError(err.into()))
+    }
+
+    async fn get_me(&self) -> BotResult<Me> {
+        self.0
+            .get_me()
+            .await
+            .map_err(|err| BotError::InternalError(err.into()))
+    }
+
+    async fn send_message(&self, message: MessageType) -> BotResult {
+        match message {
+            MessageType::UserHasBeenOutbidForBuyer { listing, buyer } => {
+                self.send_user_has_been_outbid(listing, buyer).await?;
+            }
+            MessageType::BidHasBeenPlacedForSeller {
+                listing,
+                buyer,
+                seller,
+                bid,
+            } => {
+                self.send_bid_has_been_placed(listing, buyer, seller, bid)
+                    .await?;
+            }
+            MessageType::BidHasBeenConfirmedForBuyer { listing, bid } => {
+                self.send_bid_has_been_confirmed(listing, bid).await?;
+            }
+            MessageType::BidInvalidListingExpired { listing, buyer } => {
+                self.send_bid_invalid_listing_expired(listing, buyer)
+                    .await?;
+            }
+            MessageType::UserHasWonListingForSeller {
+                listing,
+                buyer,
+                seller,
+                bid,
+            } => {
+                self.send_user_has_won_listing_for_seller(listing, buyer, seller, bid)
+                    .await?;
+            }
+            MessageType::UserHasWonListingForBuyer {
+                listing,
+                buyer,
+                seller,
+                bid,
+            } => {
+                self.send_user_has_won_listing_for_buyer(listing, buyer, seller, bid)
+                    .await?;
+            }
+            MessageType::UserHasLostListingForBuyer {
+                listing,
+                buyer,
+                seller,
+            } => {
+                self.send_user_has_lost_listing_for_buyer(listing, buyer, seller)
+                    .await?;
+            }
+            MessageType::ListingExpiredWithNoWinnerForSeller { listing, seller } => {
+                self.send_listing_expired_with_no_winner_for_seller(listing, seller)
+                    .await?;
+            }
+        }
+        Ok(())
+    }
+}
+
+impl BotMessageSender {
+    async fn send_user_has_been_outbid(
+        &self,
+        listing: PersistedListing,
+        buyer: PersistedUser,
+    ) -> BotResult {
+        self.with_target(buyer.into())
+            .send_html_message(
+                format!(
+                    "You have been outbid for {title}",
+                    title = listing.base.title
+                ),
+                None,
+            )
+            .await
+    }
+
+    async fn send_bid_has_been_placed(
+        &self,
+        listing: PersistedListing,
+        buyer: PersistedUser,
+        seller: PersistedUser,
+        bid: PersistedBid,
+    ) -> BotResult {
+        self.with_target(seller.into())
+            .send_html_message(
+                format!(
+                    "A bid was placed on {title} for <b>{bid_amount}</b> by {buyer}",
+                    bid_amount = bid.bid_amount.with_type(listing.base.currency_type),
+                    title = listing.base.title,
+                    buyer = user_name_or_link(&buyer),
+                ),
+                Some(
+                    InlineKeyboardMarkup::default().append_row([InlineKeyboardButton::callback(
+                        "View Details",
+                        StartCommandData::ViewListingDetailsAsBuyer(listing.persisted.id),
+                    )]),
+                ),
+            )
+            .await
+    }
+
+    async fn send_bid_has_been_confirmed(
+        &self,
+        listing: PersistedListing,
+        bid: PersistedBid,
+    ) -> BotResult {
+        self.send_html_message(
+            format!(
+                "Bid placed for <b>{bid_amount}</b> on {title}",
+                bid_amount = bid.bid_amount.with_type(listing.base.currency_type),
+                title = listing.base.title,
+            ),
+            None,
+        )
+        .await
+    }
+
+    async fn send_bid_invalid_listing_expired(
+        &self,
+        listing: PersistedListing,
+        buyer: PersistedUser,
+    ) -> BotResult {
+        self.with_target(buyer.into())
+            .send_html_message(
+                format!(
+                    "Auction <b>{title}</b> already ended on <b>{ends_at}</b>",
+                    title = listing.base.title,
+                    ends_at = listing.base.ends_at.format("%Y-%m-%d %H:%M:%S")
+                ),
+                None,
+            )
+            .await
+    }
+
+    async fn send_user_has_won_listing_for_seller(
+        &self,
+        listing: PersistedListing,
+        buyer: PersistedUser,
+        seller: PersistedUser,
+        bid: PersistedBid,
+    ) -> BotResult {
+        self.with_target(seller.into())
+            .send_html_message(
+                format!(
+                    "<b>{buyer}</b> has won {title} for <b>{bid_amount}</b>",
+                    buyer = user_name_or_link(&buyer),
+                    title = listing.base.title,
+                    bid_amount = bid.bid_amount.with_type(listing.base.currency_type),
+                ),
+                None,
+            )
+            .await
+    }
+
+    async fn send_user_has_won_listing_for_buyer(
+        &self,
+        listing: PersistedListing,
+        buyer: PersistedUser,
+        seller: PersistedUser,
+        bid: PersistedBid,
+    ) -> BotResult {
+        self.with_target(buyer.into())
+            .send_html_message(
+                format!(
+                    "You have won {title} by {seller} for <b>{bid_amount}</b>",
+                    title = listing.base.title,
+                    seller = user_name_or_link(&seller),
+                    bid_amount = bid.bid_amount.with_type(listing.base.currency_type),
+                ),
+                None,
+            )
+            .await
+    }
+
+    async fn send_user_has_lost_listing_for_buyer(
+        &self,
+        listing: PersistedListing,
+        buyer: PersistedUser,
+        seller: PersistedUser,
+    ) -> BotResult {
+        self.with_target(buyer.into())
+            .send_html_message(
+                format!(
+                    "Auction {title} by {seller} has ended, and you were not the winner",
+                    title = listing.base.title,
+                    seller = user_name_or_link(&seller),
+                ),
+                None,
+            )
+            .await
+    }
+
+    async fn send_listing_expired_with_no_winner_for_seller(
+        &self,
+        listing: PersistedListing,
+        seller: PersistedUser,
+    ) -> BotResult {
+        self.with_target(seller.into())
+            .send_html_message(
+                format!(
+                    "Auction {title} has ended with no winner",
+                    title = listing.base.title
+                ),
+                None,
+            )
+            .await
+    }
+}
--- a/src/bot_result.rs
+++ b/src/bot_result.rs
@@ -0,0 +1,24 @@
+use anyhow::Error;
+use teloxide::dispatching::DpHandlerDescription;
+
+#[derive(thiserror::Error, Debug)]
+pub enum BotError {
+    #[error("User visible error: {0}")]
+    UserVisibleError(String),
+    #[error(transparent)]
+    InternalError(#[from] anyhow::Error),
+}
+impl BotError {
+    pub fn user_visible(msg: impl Into<String>) -> Self {
+        Self::UserVisibleError(msg.into())
+    }
+    pub fn internal(msg: impl Into<Error>) -> Self {
+        Self::InternalError(msg.into())
+    }
+    pub fn internal_str(msg: impl Into<String>) -> Self {
+        Self::InternalError(anyhow::anyhow!(msg.into()))
+    }
+}
+
+pub type BotResult<T = ()> = Result<T, BotError>;
+pub type BotHandler = dptree::Handler<'static, BotResult, DpHandlerDescription>;
--- a/src/commands/help.rs
+++ b/src/commands/help.rs
@@ -1,8 +1,7 @@
-use teloxide::{prelude::*, types::Message, utils::command::BotCommands, Bot};
+use crate::{App, BotResult, Command};
+use teloxide::utils::command::BotCommands;

-use crate::{Command, HandlerResult};
-
-pub async fn handle_help(bot: Bot, msg: Message) -> HandlerResult {
+pub async fn handle_help(app: App) -> BotResult {
    let help_message = format!(
        "📋 Available Commands:\n\n{}\n\n\
        📧 Support: Contact @admin for help\n\
@@ -10,6 +9,6 @@ pub async fn handle_help(bot: Bot, msg: Message) -> HandlerResult {
        Command::descriptions()
    );

-    bot.send_message(msg.chat.id, help_message).await?;
+    app.bot.send_html_message(help_message, None).await?;
    Ok(())
 }
--- a/src/commands/mod.rs
+++ b/src/commands/mod.rs
@@ -3,9 +3,9 @@ pub mod my_bids;
 pub mod my_listings;
 pub mod new_listing;
 pub mod settings;
-pub mod start;
+mod start;

 pub use help::handle_help;
 pub use my_bids::handle_my_bids;
 pub use settings::handle_settings;
-pub use start::handle_start;
+pub use start::{enter_main_menu, handle_main_menu_callback, handle_start};
--- a/src/commands/my_bids.rs
+++ b/src/commands/my_bids.rs
@@ -1,16 +1,16 @@
+use crate::{App, BotResult};
 use log::info;
-use teloxide::{prelude::*, types::Message, Bot};
+use teloxide::types::Message;

-use crate::HandlerResult;
-
-pub async fn handle_my_bids(bot: Bot, msg: Message) -> HandlerResult {
+pub async fn handle_my_bids(app: App, msg: Message) -> BotResult {
    let response = "🎯 My Bids (Coming Soon)\n\n\
        Here you'll be able to view:\n\
        • Your active bids\n\
        • Bid status (winning/outbid)\n\
        • Proxy bid settings\n\
        • Auction end times\n\n\
-        Feature in development! 🏗️";
+        Feature in development! 🏗️"
+        .to_string();

    info!(
        "User {} ({}) checked their bids",
@@ -18,6 +18,6 @@ pub async fn handle_my_bids(bot: Bot, msg: Message) -> HandlerResult {
        msg.chat.id
    );

-    bot.send_message(msg.chat.id, response).await?;
+    app.bot.send_html_message(response, None).await?;
    Ok(())
 }
--- a/src/commands/my_listings.rs
+++ b/src/commands/my_listings.rs
@@ -1,268 +0,0 @@
-use crate::{
-    case,
-    db::{Listing, ListingDAO, ListingId, User, UserDAO},
-    keyboard_buttons,
-    message_utils::{extract_callback_data, pluralize_with_count, send_message, MessageTarget},
-    Command, DialogueRootState, HandlerResult, RootDialogue,
-};
-use serde::{Deserialize, Serialize};
-use sqlx::SqlitePool;
-use teloxide::{
-    dispatching::{DpHandlerDescription, UpdateFilterExt},
-    prelude::*,
-    types::{InlineKeyboardButton, Message},
-    Bot,
-};
-
-#[derive(Debug, Clone, PartialEq, Eq, Hash, Serialize, Deserialize)]
-pub enum MyListingsState {
-    ViewingListings,
-    ManagingListing(ListingId),
-    EditingListing(ListingId),
-}
-impl From<MyListingsState> for DialogueRootState {
-    fn from(state: MyListingsState) -> Self {
-        DialogueRootState::MyListings(state)
-    }
-}
-
-keyboard_buttons! {
-    enum ManageListingButtons {
-        [
-            Edit("✏️ Edit", "manage_listing_edit"),
-            Delete("🗑️ Delete", "manage_listing_delete"),
-        ],
-        [
-            Back("⬅️ Back", "manage_listing_back"),
-        ]
-    }
-}
-
-pub fn my_listings_handler() -> Handler<'static, HandlerResult, DpHandlerDescription> {
-    dptree::entry()
-        .branch(
-            Update::filter_message().filter_command::<Command>().branch(
-                dptree::case![Command::MyListings].endpoint(handle_my_listings_command_input),
-            ),
-        )
-        .branch(
-            Update::filter_callback_query()
-                .branch(
-                    // Callback when user taps a listing ID button to manage that listing
-                    case![DialogueRootState::MyListings(
-                        MyListingsState::ViewingListings
-                    )]
-                    .endpoint(handle_viewing_listings_callback),
-                )
-                .branch(
-                    case![DialogueRootState::MyListings(
-                        MyListingsState::ManagingListing(listing_id)
-                    )]
-                    .endpoint(handle_managing_listing_callback),
-                ),
-        )
-}
-
-async fn handle_my_listings_command_input(
-    db_pool: SqlitePool,
-    bot: Bot,
-    dialogue: RootDialogue,
-    msg: Message,
-) -> HandlerResult {
-    let from = msg.from.unwrap();
-    show_listings_for_user(db_pool, dialogue, bot, from.id, msg.chat).await?;
-    Ok(())
-}
-
-async fn show_listings_for_user(
-    db_pool: SqlitePool,
-    dialogue: RootDialogue,
-    bot: Bot,
-    user: teloxide::types::UserId,
-    target: impl Into<MessageTarget>,
-) -> HandlerResult {
-    // If we reach here, show the listings menu
-    let user = match UserDAO::find_by_telegram_id(&db_pool, user).await? {
-        Some(user) => user,
-        None => {
-            send_message(
-                &bot,
-                target,
-                "You don't have an account. Try creating an auction first.",
-                None,
-            )
-            .await?;
-            return Err(anyhow::anyhow!("User not found"));
-        }
-    };
-
-    // Transition to ViewingListings state
-    dialogue.update(MyListingsState::ViewingListings).await?;
-
-    let listings = ListingDAO::find_by_seller(&db_pool, user.id).await?;
-    if listings.is_empty() {
-        send_message(
-            &bot,
-            target,
-            "📋 <b>My Listings</b>\n\n\
-            You don't have any listings yet.\n\
-            Use /newlisting to create your first listing!",
-            None,
-        )
-        .await?;
-        return Ok(());
-    }
-
-    // Create keyboard with buttons for each listing
-    let mut keyboard = teloxide::types::InlineKeyboardMarkup::default();
-    for listing in &listings {
-        keyboard = keyboard.append_row(vec![InlineKeyboardButton::callback(
-            listing.base.title.to_string(),
-            listing.base.id.to_string(),
-        )]);
-    }
-
-    let mut response = format!(
-        "📋 <b>My Listings</b>\n\n\
-        You have {}.\n\n",
-        pluralize_with_count(listings.len(), "listing", "listings")
-    );
-
-    // Add each listing with its ID and title
-    for listing in &listings {
-        response.push_str(&format!(
-            "• <b>ID {}:</b> {}\n",
-            listing.base.id, listing.base.title
-        ));
-    }
-
-    response.push_str("\nTap a listing ID below to view details:");
-    send_message(&bot, target, response, Some(keyboard)).await?;
-    Ok(())
-}
-
-async fn handle_viewing_listings_callback(
-    db_pool: SqlitePool,
-    bot: Bot,
-    dialogue: RootDialogue,
-    callback_query: CallbackQuery,
-) -> HandlerResult {
-    let (data, from, message_id) = extract_callback_data(&bot, callback_query).await?;
-    let target = (from.clone(), message_id);
-
-    let listing_id = ListingId::new(data.parse::<i64>()?);
-    let (_, listing) =
-        get_user_and_listing(&db_pool, &bot, from.id, listing_id, target.clone()).await?;
-    dialogue
-        .update(MyListingsState::ManagingListing(listing_id))
-        .await?;
-    show_listing_details(&bot, listing, target).await?;
-
-    Ok(())
-}
-
-async fn show_listing_details(
-    bot: &Bot,
-    listing: Listing,
-    target: impl Into<MessageTarget>,
-) -> HandlerResult {
-    let response = format!(
-        "🔍 <b>Viewing Listing Details</b>\n\n\
-        <b>Title:</b> {}\n\
-        <b>Description:</b> {}\n\
-        <b>ID:</b> {}",
-        listing.base.title,
-        listing
-            .base
-            .description
-            .as_deref()
-            .unwrap_or("No description"),
-        listing.base.id
-    );
-
-    send_message(
-        bot,
-        target,
-        response,
-        Some(ManageListingButtons::to_keyboard()),
-    )
-    .await?;
-    Ok(())
-}
-
-async fn handle_managing_listing_callback(
-    db_pool: SqlitePool,
-    bot: Bot,
-    dialogue: RootDialogue,
-    callback_query: CallbackQuery,
-    listing_id: ListingId,
-) -> HandlerResult {
-    let (data, from, message_id) = extract_callback_data(&bot, callback_query).await?;
-    let target = (from.clone(), message_id);
-
-    let button = ManageListingButtons::try_from(data.as_str())
-        .map_err(|_| anyhow::anyhow!("Invalid ManageListingButtons callback data: {}", data))?;
-
-    match button {
-        ManageListingButtons::Edit => {
-            let (_, listing) =
-                get_user_and_listing(&db_pool, &bot, from.id, listing_id, target.clone()).await?;
-            dialogue
-                .update(MyListingsState::EditingListing(listing.base.id))
-                .await?;
-        }
-        ManageListingButtons::Delete => {
-            ListingDAO::delete_listing(&db_pool, listing_id).await?;
-            send_message(&bot, target, "Listing deleted.", None).await?;
-        }
-        ManageListingButtons::Back => {
-            dialogue.update(MyListingsState::ViewingListings).await?;
-            show_listings_for_user(db_pool, dialogue, bot, from.id, target).await?;
-        }
-    }
-
-    Ok(())
-}
-
-async fn get_user_and_listing(
-    db_pool: &SqlitePool,
-    bot: &Bot,
-    user_id: teloxide::types::UserId,
-    listing_id: ListingId,
-    target: impl Into<MessageTarget>,
-) -> HandlerResult<(User, Listing)> {
-    let user = match UserDAO::find_by_telegram_id(db_pool, user_id).await? {
-        Some(user) => user,
-        None => {
-            send_message(
-                bot,
-                target,
-                "❌ You don't have an account. Try creating an auction first.",
-                None,
-            )
-            .await?;
-            return Err(anyhow::anyhow!("User not found"));
-        }
-    };
-
-    let listing = match ListingDAO::find_by_id(db_pool, listing_id).await? {
-        Some(listing) => listing,
-        None => {
-            send_message(bot, target, "❌ Listing not found.", None).await?;
-            return Err(anyhow::anyhow!("Listing not found"));
-        }
-    };
-
-    if listing.base.seller_id != user.id {
-        send_message(
-            bot,
-            target,
-            "❌ You can only manage your own auctions.",
-            None,
-        )
-        .await?;
-        return Err(anyhow::anyhow!("User does not own listing"));
-    }
-
-    Ok((user, listing))
-}
--- a/src/commands/my_listings/keyboard.rs
+++ b/src/commands/my_listings/keyboard.rs
@@ -0,0 +1,70 @@
+use crate::{
+    db::{listing::PersistedListing, DbListingId},
+    keyboard_buttons,
+};
+use regex::Regex;
+use teloxide::types::InlineKeyboardButton;
+
+// keyboard_buttons! {
+//     pub enum MyListingsButtons {
+//         // SelectListing("Select Listing", "my_listings:", ListingDbId ),
+//         SelectListing("Select Listing", "my_listings:"),
+//         BackToMenu("⬅️ Back to Menu", "my_listings_back_to_menu"),
+//     }
+// }
+
+pub enum MyListingsButtons {
+    SelectListing(DbListingId),
+    NewListing,
+}
+impl MyListingsButtons {
+    pub fn listing_into_button(listing: &PersistedListing) -> InlineKeyboardButton {
+        let text = format!(
+            "{} {} - {}",
+            listing.fields.listing_type().emoji_str(),
+            listing.fields.listing_type(),
+            listing.base.title,
+        );
+        InlineKeyboardButton::callback(text, Self::encode_listing_id(listing.persisted.id))
+    }
+
+    pub fn new_listing_into_button() -> InlineKeyboardButton {
+        InlineKeyboardButton::callback("➕ New Listing", "my_listings_new_listing")
+    }
+
+    fn encode_listing_id(listing_id: DbListingId) -> String {
+        format!("my_listings:{listing_id}")
+    }
+
+    fn decode_listing_id(value: &str) -> Option<DbListingId> {
+        let re = Regex::new(r"my_listings:(\d+)").ok()?;
+        let caps = re.captures(value)?;
+        let listing_id = caps.get(1)?.as_str().parse::<i64>().ok()?;
+        Some(DbListingId::new(listing_id))
+    }
+}
+
+impl TryFrom<&str> for MyListingsButtons {
+    type Error = anyhow::Error;
+    fn try_from(value: &str) -> Result<Self, Self::Error> {
+        if let Some(listing_id) = Self::decode_listing_id(value) {
+            return Ok(MyListingsButtons::SelectListing(listing_id));
+        }
+        match value {
+            "my_listings_new_listing" => Ok(MyListingsButtons::NewListing),
+            _ => anyhow::bail!("Unknown MyListingsButtons: {value}"),
+        }
+    }
+}
+
+keyboard_buttons! {
+    pub enum ManageListingButtons {
+        [
+            PreviewMessage("👀 Preview", "manage_listing_preview"),
+            ForwardListing("↪️ Forward", "manage_listing_forward"),
+        ],
+        [Edit("✏️ Edit", "manage_listing_edit"),],
+        [Delete("🗑️ Delete", "manage_listing_delete"),],
+        [Back("⬅️ Back", "manage_listing_back"),]
+    }
+}
--- a/src/commands/my_listings/mod.rs
+++ b/src/commands/my_listings/mod.rs
@@ -0,0 +1,462 @@
+mod keyboard;
+
+use std::ops::Deref;
+
+use crate::{
+    case,
+    commands::{
+        enter_main_menu,
+        my_listings::keyboard::{ManageListingButtons, MyListingsButtons},
+        new_listing::{
+            enter_edit_listing_draft, enter_select_new_listing_type, keyboard::NavKeyboardButtons,
+            messages::steps_for_listing_type, ListingDraft,
+        },
+    },
+    db::{
+        listing::{ListingFields, PersistedListing},
+        user::PersistedUser,
+        DAOs, DbListingId, ListingType,
+    },
+    handle_error::with_error_handler,
+    handler_utils::{find_listing_by_id, find_or_create_db_user_from_update},
+    message_utils::{extract_callback_data, pluralize_with_count, user_name_or_link},
+    start_command_data::StartCommandData,
+    App, BotError, BotResult, Command, DialogueRootState, RootDialogue,
+};
+use anyhow::Context;
+use log::info;
+use serde::{Deserialize, Serialize};
+use teloxide::{
+    dispatching::{DpHandlerDescription, UpdateFilterExt},
+    prelude::*,
+    types::{
+        InlineKeyboardButton, InlineKeyboardMarkup, InlineQueryResult, InlineQueryResultArticle,
+        InputMessageContent, InputMessageContentText, ParseMode, User,
+    },
+};
+
+#[derive(Debug, Clone, PartialEq, Eq, Hash, Serialize, Deserialize)]
+pub enum MyListingsState {
+    ViewingListings,
+    ManagingListing(DbListingId),
+}
+impl From<MyListingsState> for DialogueRootState {
+    fn from(state: MyListingsState) -> Self {
+        DialogueRootState::MyListings(state)
+    }
+}
+
+pub fn my_listings_inline_handler() -> Handler<'static, BotResult, DpHandlerDescription> {
+    Update::filter_inline_query()
+        .filter_map_async(inline_query_extract_forward_listing)
+        .endpoint(handle_forward_listing)
+}
+
+pub fn my_listings_handler() -> Handler<'static, BotResult, DpHandlerDescription> {
+    dptree::entry()
+        .branch(
+            Update::filter_message()
+                .filter_map(StartCommandData::get_from_update)
+                .filter_map(StartCommandData::get_view_listing_details_as_buyer_start_command)
+                .filter_map_async(find_listing_by_id)
+                .endpoint(with_error_handler(handle_view_listing_details)),
+        )
+        .branch(
+            Update::filter_message().filter_command::<Command>().branch(
+                dptree::case![Command::MyListings]
+                    .filter_map_async(find_or_create_db_user_from_update)
+                    .endpoint(with_error_handler(handle_my_listings_command_input)),
+            ),
+        )
+        .branch(
+            Update::filter_callback_query()
+                .branch(
+                    // Callback when user taps a listing ID button to manage that listing
+                    case![DialogueRootState::MyListings(
+                        MyListingsState::ViewingListings
+                    )]
+                    .endpoint(with_error_handler(handle_viewing_listings_callback)),
+                )
+                .branch(
+                    case![DialogueRootState::MyListings(
+                        MyListingsState::ManagingListing(listing_id)
+                    )]
+                    .endpoint(with_error_handler(handle_managing_listing_callback)),
+                ),
+        )
+}
+
+async fn handle_view_listing_details(app: App, listing: PersistedListing) -> BotResult {
+    send_listing_details_message(app, listing, None).await?;
+    Ok(())
+}
+
+async fn inline_query_extract_forward_listing(
+    app: App,
+    inline_query: InlineQuery,
+) -> Option<PersistedListing> {
+    let query = &inline_query.query;
+    info!("Try to extract forward listing from query: {query}");
+    if !query.starts_with("forward_listing:") {
+        return None;
+    }
+    let listing_id_str = query.split(":").nth(1)?;
+    let listing_id = DbListingId::new(listing_id_str.parse::<i64>().ok()?);
+    let listing = app
+        .daos
+        .listing
+        .find_by_id(listing_id)
+        .await
+        .unwrap_or(None)?;
+    Some(listing)
+}
+
+async fn handle_forward_listing(
+    app: App,
+    inline_query: InlineQuery,
+    listing: PersistedListing,
+) -> BotResult {
+    info!("Handling forward listing inline query for listing {listing:?}");
+
+    // Create inline keyboard with auction interaction buttons
+    let keyboard = InlineKeyboardMarkup::default()
+        .append_row([
+            InlineKeyboardButton::url(
+                "💰 Place Bid",
+                app.url_for_start_command(StartCommandData::PlaceBidOnListing(
+                    listing.persisted.id,
+                )),
+            ),
+            InlineKeyboardButton::callback(
+                "👀 Watch",
+                format!("inline_watch:{}", listing.persisted.id),
+            ),
+        ])
+        .append_row([InlineKeyboardButton::url(
+            "🔗 View Full Details",
+            app.url_for_start_command(StartCommandData::ViewListingDetailsAsBuyer(
+                listing.persisted.id,
+            )),
+        )]);
+
+    // Get the current price based on listing type
+    let current_price = get_listing_current_price(&listing);
+    let seller = app
+        .daos
+        .user
+        .find_by_id(listing.base.seller_id)
+        .await?
+        .ok_or(BotError::internal_str("Seller not found"))?;
+
+    // Create a more detailed message content for the shared listing
+    let message_content = format!(
+        "🎯 <b>{title}</b> by {seller}\n\n\
+        📝 {description}\n\n\
+        💰 <b>Current Price:</b> ${current_price}\n\
+        ⏰ <b>Ends:</b> {ends_at}\n\n\
+        <i>Use the buttons below to interact! ⬇️</i>",
+        title = listing.base.title,
+        seller = user_name_or_link(&seller),
+        description = listing
+            .base
+            .description
+            .as_deref()
+            .unwrap_or("No description"),
+        ends_at = listing.base.ends_at.format("%b %d, %Y at %H:%M UTC")
+    );
+
+    app.bot
+        .answer_inline_query(
+            inline_query.id,
+            vec![InlineQueryResult::Article(
+                InlineQueryResultArticle::new(
+                    listing.persisted.id.to_string(),
+                    format!("💰 {} - ${}", listing.base.title, current_price),
+                    InputMessageContent::Text(
+                        InputMessageContentText::new(message_content).parse_mode(ParseMode::Html),
+                    ),
+                )
+                .description(&listing.base.title)
+                .reply_markup(keyboard), // Add the inline keyboard here!
+            )],
+        )
+        .await
+        .map_err(|e| anyhow::anyhow!("Error answering inline query: {e:?}"))?;
+    Ok(())
+}
+
+/// Helper function to get the current price of a listing based on its type
+fn get_listing_current_price(listing: &PersistedListing) -> String {
+    use crate::db::listing::ListingFields;
+
+    match &listing.fields {
+        ListingFields::BasicAuction(fields) => {
+            // For basic auctions, show starting bid (in a real app, you'd show current highest bid)
+            format!("{}", fields.starting_bid)
+        }
+        ListingFields::MultiSlotAuction(fields) => {
+            // For multi-slot auctions, show starting bid
+            format!("{}", fields.starting_bid)
+        }
+        ListingFields::FixedPriceListing(fields) => {
+            // For fixed price listings, show the fixed price
+            format!("{}", fields.buy_now_price)
+        }
+        ListingFields::BlindAuction(fields) => {
+            // For blind auctions, show starting bid
+            format!("{}", fields.starting_bid)
+        }
+    }
+}
+
+async fn handle_my_listings_command_input(
+    app: App,
+    dialogue: RootDialogue,
+    user: PersistedUser,
+) -> BotResult {
+    enter_my_listings(app, dialogue, user, None).await?;
+    Ok(())
+}
+
+pub async fn enter_my_listings(
+    app: App,
+    dialogue: RootDialogue,
+    user: PersistedUser,
+    flash: Option<String>,
+) -> BotResult {
+    // Transition to ViewingListings state
+    dialogue
+        .update(MyListingsState::ViewingListings)
+        .await
+        .context("failed to update dialogue")?;
+
+    let listings = app.daos.listing.find_by_seller(user.persisted.id).await?;
+    // Create keyboard with buttons for each listing
+    let mut keyboard = teloxide::types::InlineKeyboardMarkup::default();
+    for listing in &listings {
+        keyboard = keyboard.append_row(vec![MyListingsButtons::listing_into_button(listing)]);
+    }
+    keyboard = keyboard.append_row(vec![
+        MyListingsButtons::new_listing_into_button(),
+        NavKeyboardButtons::Back.to_button(),
+    ]);
+
+    if listings.is_empty() {
+        app.bot
+            .send_html_message(
+                "📋 <b>My Listings</b>\n\n\
+            You don't have any listings yet."
+                    .to_string(),
+                Some(keyboard),
+            )
+            .await?;
+        return Ok(());
+    }
+
+    let mut response = format!(
+        "📋 <b>My Listings</b>\n\n\
+        You have {}.\n\n\
+        Select a listing to view details",
+        pluralize_with_count(listings.len(), "listing", "listings")
+    );
+
+    if let Some(flash) = flash {
+        response = format!("{flash}\n\n{response}");
+    }
+
+    app.bot.send_html_message(response, Some(keyboard)).await?;
+    Ok(())
+}
+
+async fn handle_viewing_listings_callback(
+    app: App,
+    dialogue: RootDialogue,
+    callback_query: CallbackQuery,
+    user: PersistedUser,
+) -> BotResult {
+    let data = extract_callback_data(app.bot.deref(), callback_query).await?;
+
+    if let Ok(NavKeyboardButtons::Back) = NavKeyboardButtons::try_from(data.as_str()) {
+        return enter_main_menu(app, dialogue).await;
+    }
+
+    // Check if it's the back to menu button
+    let button = MyListingsButtons::try_from(data.as_str())?;
+    match button {
+        MyListingsButtons::SelectListing(listing_id) => {
+            let listing = get_listing_for_user(&app.daos, user, listing_id).await?;
+            enter_show_listing_details(app, dialogue, listing).await?;
+        }
+        MyListingsButtons::NewListing => {
+            enter_select_new_listing_type(app, dialogue).await?;
+        }
+    }
+
+    Ok(())
+}
+
+async fn enter_show_listing_details(
+    app: App,
+    dialogue: RootDialogue,
+    listing: PersistedListing,
+) -> BotResult {
+    let listing_id = listing.persisted.id;
+    dialogue
+        .update(MyListingsState::ManagingListing(listing_id))
+        .await
+        .context("failed to update dialogue")?;
+    let keyboard = InlineKeyboardMarkup::default()
+        .append_row([
+            ManageListingButtons::PreviewMessage.to_button(),
+            InlineKeyboardButton::switch_inline_query(
+                ManageListingButtons::ForwardListing.title(),
+                format!(
+                    "forward_listing:{listing_id}:{nonce}",
+                    nonce = uuid::Uuid::new_v4()
+                ),
+            ),
+        ])
+        .append_row([
+            ManageListingButtons::Edit.to_button(),
+            ManageListingButtons::Delete.to_button(),
+        ])
+        .append_row([ManageListingButtons::Back.to_button()]);
+    send_listing_details_message(app, listing, Some(keyboard)).await?;
+    Ok(())
+}
+
+async fn send_listing_details_message(
+    app: App,
+    listing: PersistedListing,
+    keyboard: Option<InlineKeyboardMarkup>,
+) -> BotResult {
+    let listing_type = Into::<ListingType>::into(&listing.fields);
+    let mut response_lines = vec![format!("🔍 <b>{listing_type} Details</b>")];
+    response_lines.push("".to_string());
+
+    let draft = ListingDraft::from_persisted(listing);
+    for step in steps_for_listing_type(listing_type) {
+        let field_value = match (step.get_field_value)(&draft) {
+            Ok(value) => value.unwrap_or_else(|| "(none)".to_string()),
+            Err(_) => continue,
+        };
+        response_lines.push(format!("<b>{}:</b> {}", step.field_name, field_value));
+    }
+    app.bot
+        .send_html_message(response_lines.join("\n"), keyboard)
+        .await?;
+    Ok(())
+}
+
+async fn handle_managing_listing_callback(
+    app: App,
+    dialogue: RootDialogue,
+    callback_query: CallbackQuery,
+    user: PersistedUser,
+    listing_id: DbListingId,
+) -> BotResult {
+    let from = callback_query.from.clone();
+    let data = extract_callback_data(&app.bot, callback_query).await?;
+
+    match ManageListingButtons::try_from(data.as_str())? {
+        ManageListingButtons::PreviewMessage => {
+            let listing = app
+                .daos
+                .listing
+                .find_by_id(listing_id)
+                .await?
+                .ok_or(anyhow::anyhow!("Listing not found"))?;
+            send_preview_listing_message(app, listing, from).await?;
+        }
+        ManageListingButtons::ForwardListing => {
+            unimplemented!("Forward listing not implemented");
+        }
+        ManageListingButtons::Edit => {
+            let listing = get_listing_for_user(&app.daos, user, listing_id).await?;
+            let draft = ListingDraft::from_persisted(listing);
+            enter_edit_listing_draft(app, draft, dialogue, None).await?;
+        }
+        ManageListingButtons::Delete => {
+            app.daos.listing.delete_listing(listing_id).await?;
+            enter_my_listings(app, dialogue, user, Some("Listing deleted.".to_string())).await?;
+        }
+        ManageListingButtons::Back => {
+            enter_my_listings(app, dialogue, user, None).await?;
+        }
+    }
+
+    Ok(())
+}
+
+fn keyboard_for_listing(listing: &PersistedListing) -> InlineKeyboardMarkup {
+    let mut keyboard = InlineKeyboardMarkup::default();
+    match listing.fields {
+        ListingFields::FixedPriceListing(_) => {
+            keyboard = keyboard.append_row([InlineKeyboardButton::callback(
+                "Buy",
+                "fixed_price_listing_buy",
+            )]);
+        }
+        ListingFields::BasicAuction(_) => {
+            keyboard = keyboard.append_row([
+                InlineKeyboardButton::callback("Submit Bid", "basic_auction_bid"),
+                InlineKeyboardButton::callback("Buy It Now", "basic_auction_buy_it_now"),
+            ]);
+        }
+        ListingFields::MultiSlotAuction(_) => {
+            keyboard = keyboard.append_row([InlineKeyboardButton::callback(
+                "Submit Bid",
+                "multi_slot_auction_submit_bid",
+            )]);
+        }
+        ListingFields::BlindAuction(_) => {
+            keyboard = keyboard.append_row([InlineKeyboardButton::callback(
+                "Submit Bid",
+                "blind_auction_submit_bid",
+            )]);
+        }
+    };
+    keyboard
+}
+
+async fn send_preview_listing_message(
+    app: App,
+    listing: PersistedListing,
+    from: User,
+) -> BotResult {
+    let mut response_lines = vec![];
+    response_lines.push(format!("<b>{}</b>", &listing.base.title));
+    if let Some(description) = &listing.base.description {
+        response_lines.push(description.to_owned());
+    }
+
+    app.bot
+        .with_target(from.into())
+        .send_html_message(
+            response_lines.join("\n\n"),
+            Some(keyboard_for_listing(&listing)),
+        )
+        .await?;
+    Ok(())
+}
+
+async fn get_listing_for_user(
+    daos: &DAOs,
+    user: PersistedUser,
+    listing_id: DbListingId,
+) -> BotResult<PersistedListing> {
+    let listing = match daos.listing.find_by_id(listing_id).await? {
+        Some(listing) => listing,
+        None => {
+            return Err(BotError::UserVisibleError("❌ Listing not found.".into()));
+        }
+    };
+
+    if listing.base.seller_id != user.persisted.id {
+        return Err(BotError::UserVisibleError(
+            "❌ You can only manage your own auctions.".into(),
+        ));
+    }
+
+    Ok(listing)
+}
--- a/src/commands/new_listing/callbacks.rs
+++ b/src/commands/new_listing/callbacks.rs
@@ -0,0 +1,300 @@
+//! Callback handling for the new listing wizard
+//!
+//! This module handles all callback query processing for buttons
+//! in the new listing creation and editing workflows.
+
+use std::str::FromStr;
+
+use crate::{
+    commands::{
+        my_listings::enter_my_listings,
+        new_listing::{
+            enter_select_new_listing_type,
+            field_processing::{transition_to_field, update_field_on_draft},
+            keyboard::*,
+            messages::*,
+            types::{ListingDraft, ListingField},
+            ui::enter_confirm_save_listing,
+        },
+    },
+    db::{user::PersistedUser, CurrencyType, ListingDuration, ListingType, MoneyAmount},
+    message_utils::*,
+    App, BotResult, RootDialogue,
+};
+use log::{error, info};
+use teloxide::types::CallbackQuery;
+
+/// Handle callbacks during the listing type selection phase
+pub async fn handle_selecting_listing_type_callback(
+    app: App,
+    dialogue: RootDialogue,
+    user: PersistedUser,
+    callback_query: CallbackQuery,
+) -> BotResult {
+    let data = extract_callback_data(&app.bot, callback_query).await?;
+    info!("User selected listing type: {data:?}");
+
+    if let Ok(NavKeyboardButtons::Back) = NavKeyboardButtons::try_from(data.as_str()) {
+        return enter_my_listings(app, dialogue, user, None).await;
+    }
+
+    // Parse the listing type from callback data
+    let (listing_type, type_name) = match ListingTypeKeyboardButtons::try_from(data.as_str())? {
+        ListingTypeKeyboardButtons::FixedPrice => {
+            (ListingType::FixedPriceListing, "Fixed Price Listing")
+        }
+        ListingTypeKeyboardButtons::BasicAuction => (ListingType::BasicAuction, "Basic Auction"),
+        ListingTypeKeyboardButtons::BlindAuction => (ListingType::BlindAuction, "Blind Auction"),
+        ListingTypeKeyboardButtons::MultiSlot => {
+            (ListingType::MultiSlotAuction, "Multi-Slot Auction")
+        }
+    };
+
+    // Create draft with selected listing type
+    let draft = ListingDraft::new_for_seller_with_type(user.persisted.id, listing_type);
+
+    // Transition to first field (Title)
+    transition_to_field(dialogue, ListingField::Title, draft).await?;
+
+    let response = format!(
+        "✅ <b>{} selected!</b>\n\n{}",
+        type_name,
+        get_step_message(ListingField::Title, listing_type)
+    );
+
+    app.bot
+        .send_html_message(response, get_keyboard_for_field(ListingField::Title))
+        .await?;
+
+    Ok(())
+}
+
+/// Handle callbacks during the field input phase
+pub async fn handle_awaiting_draft_field_callback(
+    app: App,
+    dialogue: RootDialogue,
+    field: ListingField,
+    draft: ListingDraft,
+    callback_query: CallbackQuery,
+) -> BotResult {
+    let data = extract_callback_data(&app.bot, callback_query).await?;
+    info!("User selected callback: {data:?}");
+
+    if let Ok(button) = NavKeyboardButtons::try_from(data.as_str()) {
+        match button {
+            NavKeyboardButtons::Back => {
+                return enter_select_new_listing_type(app, dialogue).await;
+            }
+            NavKeyboardButtons::Skip => {
+                return handle_skip_field(app, dialogue, field, draft).await;
+            }
+            NavKeyboardButtons::Cancel => {
+                return cancel_wizard(app, dialogue).await;
+            }
+        }
+    }
+
+    // Unified callback dispatch
+    match field {
+        ListingField::Slots => {
+            let button = SlotsKeyboardButtons::try_from(data.as_str())?;
+            handle_slots_callback(app, dialogue, draft, button).await
+        }
+        ListingField::StartTime => {
+            let button = StartTimeKeyboardButtons::try_from(data.as_str())?;
+            handle_start_time_callback(app, dialogue, draft, button).await
+        }
+        ListingField::EndTime => {
+            let button = DurationKeyboardButtons::try_from(data.as_str())?;
+            handle_duration_callback(app, dialogue, draft, button).await
+        }
+        ListingField::MinBidIncrement => {
+            let button = EditMinimumBidIncrementKeyboardButtons::try_from(data.as_str())?;
+            handle_starting_bid_amount_callback(app, dialogue, draft, button).await
+        }
+        ListingField::CurrencyType => {
+            let button = CurrencyTypeKeyboardButtons::try_from(data.as_str())?;
+            handle_currency_type_callback(app, dialogue, draft, button).await
+        }
+        _ => {
+            error!("Unknown callback data for field {field:?}: {data}");
+            Ok(())
+        }
+    }
+}
+
+async fn handle_skip_field(
+    app: App,
+    dialogue: RootDialogue,
+    current_field: ListingField,
+    draft: ListingDraft,
+) -> BotResult {
+    let field_name = get_field_name(current_field, draft.listing_type());
+    let next_field = get_next_field(current_field, draft.listing_type());
+    let flash = format!("✅ {field_name} skipped!");
+    if let Some(next_field) = next_field {
+        let response = format!(
+            "{}\n{}",
+            flash,
+            get_step_message(next_field, draft.listing_type())
+        );
+        transition_to_field(dialogue, next_field, draft).await?;
+        app.bot
+            .send_html_message(response, get_keyboard_for_field(next_field))
+            .await?;
+    } else {
+        enter_confirm_save_listing(app, dialogue, draft, Some(flash)).await?;
+    }
+    Ok(())
+}
+
+/// Handle slots selection callback
+async fn handle_slots_callback(
+    app: App,
+    dialogue: RootDialogue,
+    mut draft: ListingDraft,
+    button: SlotsKeyboardButtons,
+) -> BotResult {
+    let num_slots = match button {
+        SlotsKeyboardButtons::OneSlot => 1,
+        SlotsKeyboardButtons::TwoSlots => 2,
+        SlotsKeyboardButtons::FiveSlots => 5,
+        SlotsKeyboardButtons::TenSlots => 10,
+    };
+
+    update_field_on_draft(
+        ListingField::Slots,
+        &mut draft,
+        Some(num_slots.to_string().as_str()),
+    )
+    .map_err(|e| anyhow::anyhow!("Error updating slots: {e:?}"))?;
+
+    let response = format!(
+        "✅ Available slots: <b>{num_slots}</b>\n\n{}",
+        get_step_message(ListingField::StartTime, draft.listing_type())
+    );
+    transition_to_field(dialogue, ListingField::StartTime, draft).await?;
+    app.bot
+        .send_html_message(response, get_keyboard_for_field(ListingField::StartTime))
+        .await?;
+    Ok(())
+}
+
+/// Handle start time selection callback
+async fn handle_start_time_callback(
+    app: App,
+    dialogue: RootDialogue,
+    mut draft: ListingDraft,
+    button: StartTimeKeyboardButtons,
+) -> BotResult {
+    let start_time = match button {
+        StartTimeKeyboardButtons::Now => ListingDuration::zero(),
+    };
+
+    update_field_on_draft(
+        ListingField::StartTime,
+        &mut draft,
+        Some(start_time.to_string().as_str()),
+    )
+    .map_err(|e| anyhow::anyhow!("Error updating start time: {e:?}"))?;
+
+    let response = format!(
+        "✅ Listing will start: <b>{}</b>\n\n{}",
+        start_time,
+        get_step_message(ListingField::EndTime, draft.listing_type())
+    );
+    transition_to_field(dialogue, ListingField::EndTime, draft).await?;
+    app.bot
+        .send_html_message(response, get_keyboard_for_field(ListingField::EndTime))
+        .await?;
+    Ok(())
+}
+
+/// Handle duration selection callback
+async fn handle_duration_callback(
+    app: App,
+    dialogue: RootDialogue,
+    mut draft: ListingDraft,
+    button: DurationKeyboardButtons,
+) -> BotResult {
+    let duration = ListingDuration::days(match button {
+        DurationKeyboardButtons::OneDay => 1,
+        DurationKeyboardButtons::ThreeDays => 3,
+        DurationKeyboardButtons::SevenDays => 7,
+        DurationKeyboardButtons::FourteenDays => 14,
+    });
+
+    update_field_on_draft(
+        ListingField::EndTime,
+        &mut draft,
+        Some(duration.to_string().as_str()),
+    )
+    .map_err(|e| anyhow::anyhow!("Error updating duration: {e:?}"))?;
+
+    let flash = get_success_message(ListingField::EndTime, draft.listing_type());
+    enter_confirm_save_listing(app, dialogue, draft, Some(flash)).await
+}
+
+async fn handle_starting_bid_amount_callback(
+    app: App,
+    dialogue: RootDialogue,
+    mut draft: ListingDraft,
+    button: EditMinimumBidIncrementKeyboardButtons,
+) -> BotResult {
+    let starting_bid_amount = MoneyAmount::from_str(match button {
+        EditMinimumBidIncrementKeyboardButtons::OneDollar => "1.00",
+        EditMinimumBidIncrementKeyboardButtons::FiveDollars => "5.00",
+        EditMinimumBidIncrementKeyboardButtons::TenDollars => "10.00",
+    })
+    .map_err(|e| anyhow::anyhow!("Error parsing starting bid amount: {e:?}"))?;
+
+    update_field_on_draft(
+        ListingField::StartingBidAmount,
+        &mut draft,
+        Some(starting_bid_amount.to_string().as_str()),
+    )
+    .map_err(|e| anyhow::anyhow!("Error updating starting bid amount: {e:?}"))?;
+
+    let flash = get_success_message(ListingField::StartingBidAmount, draft.listing_type());
+    enter_confirm_save_listing(app, dialogue, draft, Some(flash)).await
+}
+
+async fn handle_currency_type_callback(
+    app: App,
+    dialogue: RootDialogue,
+    mut draft: ListingDraft,
+    button: CurrencyTypeKeyboardButtons,
+) -> BotResult {
+    let currency_type = match button {
+        CurrencyTypeKeyboardButtons::Usd => CurrencyType::Usd,
+        CurrencyTypeKeyboardButtons::Cad => CurrencyType::Cad,
+        CurrencyTypeKeyboardButtons::Gbp => CurrencyType::Gbp,
+        CurrencyTypeKeyboardButtons::Eur => CurrencyType::Eur,
+    };
+
+    update_field_on_draft(
+        ListingField::CurrencyType,
+        &mut draft,
+        Some(currency_type.to_string().as_str()),
+    )
+    .map_err(|e| anyhow::anyhow!("Error updating currency type: {e:?}"))?;
+
+    let next_field = ListingField::StartingBidAmount;
+    let response = format!(
+        "✅ Listing will use currency: <b>{}</b>\n\n{}",
+        currency_type,
+        get_step_message(next_field, draft.listing_type())
+    );
+    transition_to_field(dialogue, next_field, draft).await?;
+    app.bot
+        .send_html_message(response, get_keyboard_for_field(next_field))
+        .await?;
+    Ok(())
+}
+
+/// Cancel the wizard and exit
+pub async fn cancel_wizard(app: App, dialogue: RootDialogue) -> BotResult {
+    info!("User cancelled new listing wizard");
+    enter_select_new_listing_type(app, dialogue).await?;
+    Ok(())
+}
--- a/src/commands/new_listing/field_processing.rs
+++ b/src/commands/new_listing/field_processing.rs
@@ -0,0 +1,39 @@
+//! Field processing logic for the new listing wizard
+//!
+//! This module handles the core logic for processing and updating listing fields
+//! during both initial creation and editing workflows.
+
+use anyhow::Context;
+
+use crate::commands::new_listing::messages::step_for_field;
+use crate::commands::new_listing::{types::NewListingState, validations::*};
+use crate::{
+    commands::new_listing::types::{ListingDraft, ListingField},
+    BotResult, RootDialogue,
+};
+
+/// Helper function to transition to next field
+pub async fn transition_to_field(
+    dialogue: RootDialogue,
+    field: ListingField,
+    draft: ListingDraft,
+) -> BotResult {
+    dialogue
+        .update(NewListingState::AwaitingDraftField { field, draft })
+        .await
+        .context("failed to update dialogue")?;
+    Ok(())
+}
+
+/// Process field input and update the draft
+pub fn update_field_on_draft(
+    field: ListingField,
+    draft: &mut ListingDraft,
+    text: Option<&str>,
+) -> Result<(), SetFieldError> {
+    let step = step_for_field(field, draft.listing_type())
+        .ok_or(SetFieldError::UnsupportedFieldForListingType)?;
+    (step.set_field_value)(draft, text.map(|s| s.trim().to_string()))?;
+    draft.has_changes = true;
+    Ok(())
+}
--- a/src/commands/new_listing/handler_factory.rs
+++ b/src/commands/new_listing/handler_factory.rs
@@ -1,9 +1,14 @@
-use super::*;
-use crate::{case, Command, DialogueRootState, Handler};
+use super::{callbacks::*, handlers::*, types::*};
+use crate::{
+    dptree_utils::{identity, MapTwo},
+    handle_error::with_error_handler,
+    BotHandler, Command, DialogueRootState,
+};
+use dptree::case;
 use teloxide::{dptree, prelude::*, types::Update};

 // Create the dialogue handler tree for new listing wizard
-pub fn new_listing_handler() -> Handler {
+pub fn new_listing_handler() -> BotHandler {
    dptree::entry()
        .branch(
            Update::filter_message()
@@ -11,46 +16,47 @@ pub fn new_listing_handler() -> Handler {
                    dptree::entry()
                        .filter_command::<Command>()
                        .chain(case![Command::NewListing])
-                        .endpoint(handle_new_listing_command),
+                        .endpoint(with_error_handler(handle_new_listing_command)),
                )
                .branch(
-                    case![DialogueRootState::NewListing(
-                        NewListingState::AwaitingDraftField { field, draft }
-                    )]
-                    .endpoint(handle_awaiting_draft_field_input),
-                )
-                .branch(
-                    case![DialogueRootState::NewListing(
-                        NewListingState::EditingDraftField { field, draft }
-                    )]
-                    .endpoint(handle_editing_field_input),
+                    dptree::entry()
+                        .chain(case![DialogueRootState::NewListing(state)])
+                        .branch(
+                            case![NewListingState::AwaitingDraftField { field, draft }]
+                                .map2(identity::<(ListingField, ListingDraft)>)
+                                .endpoint(with_error_handler(handle_awaiting_draft_field_input)),
+                        )
+                        .branch(
+                            case![NewListingState::EditingDraftField { field, draft }]
+                                .map2(identity::<(ListingField, ListingDraft)>)
+                                .endpoint(with_error_handler(handle_editing_field_input)),
+                        ),
                ),
        )
        .branch(
            Update::filter_callback_query()
+                .chain(case![DialogueRootState::NewListing(state)])
                .branch(
-                    case![DialogueRootState::NewListing(
-                        NewListingState::AwaitingDraftField { field, draft }
-                    )]
-                    .endpoint(handle_awaiting_draft_field_callback),
+                    case![NewListingState::SelectingListingType]
+                        .endpoint(with_error_handler(handle_selecting_listing_type_callback)),
                )
                .branch(
-                    case![DialogueRootState::NewListing(
-                        NewListingState::ViewingDraft(draft)
-                    )]
-                    .endpoint(handle_viewing_draft_callback),
+                    case![NewListingState::AwaitingDraftField { field, draft }]
+                        .map2(identity::<(ListingField, ListingDraft)>)
+                        .endpoint(with_error_handler(handle_awaiting_draft_field_callback)),
                )
                .branch(
-                    case![DialogueRootState::NewListing(
-                        NewListingState::EditingDraft(draft)
-                    )]
-                    .endpoint(handle_editing_draft_callback),
+                    case![NewListingState::ViewingDraft(draft)]
+                        .endpoint(with_error_handler(handle_viewing_draft_callback)),
                )
                .branch(
-                    case![DialogueRootState::NewListing(
-                        NewListingState::EditingDraftField { field, draft }
-                    )]
-                    .endpoint(handle_editing_draft_field_callback),
+                    case![NewListingState::EditingDraft(draft)]
+                        .endpoint(with_error_handler(handle_editing_draft_callback)),
+                )
+                .branch(
+                    case![NewListingState::EditingDraftField { field, draft }]
+                        .map2(identity::<(ListingField, ListingDraft)>)
+                        .endpoint(with_error_handler(handle_editing_draft_field_callback)),
                ),
        )
 }
--- a/src/commands/new_listing/handlers.rs
+++ b/src/commands/new_listing/handlers.rs
@@ -0,0 +1,322 @@
+//! Main handler functions for the new listing wizard
+//!
+//! This module contains the primary handler functions that process
+//! user input and manage the listing creation workflow.
+
+use crate::{
+    commands::{
+        my_listings::enter_my_listings,
+        new_listing::{
+            field_processing::{transition_to_field, update_field_on_draft},
+            keyboard::{
+                ConfirmationKeyboardButtons, DurationKeyboardButtons,
+                FieldSelectionKeyboardButtons, SlotsKeyboardButtons, StartTimeKeyboardButtons,
+            },
+            messages::{
+                get_edit_success_message, get_keyboard_for_field, get_listing_type_keyboard,
+                get_listing_type_selection_message, get_next_field, get_step_message,
+                get_success_message, step_for_field,
+            },
+            types::{ListingDraft, ListingField, NewListingState},
+            ui::{display_listing_summary, enter_confirm_save_listing},
+            validations::SetFieldError,
+        },
+    },
+    db::{
+        listing::{NewListing, PersistedListing},
+        user::PersistedUser,
+        ListingDAO,
+    },
+    message_utils::*,
+    App, BotError, BotResult, DialogueRootState, RootDialogue,
+};
+use anyhow::{anyhow, Context};
+use log::info;
+use teloxide::{prelude::*, types::*};
+
+/// Handle the /newlisting command - starts the dialogue
+pub(super) async fn handle_new_listing_command(app: App, dialogue: RootDialogue) -> BotResult {
+    enter_select_new_listing_type(app, dialogue).await?;
+    Ok(())
+}
+
+pub async fn enter_select_new_listing_type(app: App, dialogue: RootDialogue) -> BotResult {
+    // Initialize the dialogue to listing type selection state
+    dialogue
+        .update(NewListingState::SelectingListingType)
+        .await
+        .context("failed to update dialogue")?;
+
+    app.bot
+        .send_html_message(
+            get_listing_type_selection_message().to_string(),
+            Some(get_listing_type_keyboard()),
+        )
+        .await?;
+    Ok(())
+}
+
+/// Handle text input for any field during creation
+pub async fn handle_awaiting_draft_field_input(
+    app: App,
+    dialogue: RootDialogue,
+    field: ListingField,
+    mut draft: ListingDraft,
+    msg: Message,
+) -> BotResult {
+    info!("User entered input step: {field:?}");
+
+    // Process the field update
+    match update_field_on_draft(field, &mut draft, msg.text()) {
+        Ok(()) => (),
+        Err(SetFieldError::ValidationFailed(e)) => {
+            return Err(BotError::user_visible(e));
+        }
+        Err(SetFieldError::UnsupportedFieldForListingType) => {
+            return Err(anyhow!("Cannot update field {field:?} for listing type").into());
+        }
+        Err(SetFieldError::FieldRequired) => {
+            return Err(anyhow!("Cannot update field {field:?} on existing listing").into());
+        }
+    };
+
+    // Handle final step or transition to next
+    if let Some(next_field) = get_next_field(field, draft.listing_type()) {
+        let response = format!(
+            "{}\n\n{}",
+            get_success_message(field, draft.listing_type()),
+            get_step_message(next_field, draft.listing_type())
+        );
+        transition_to_field(dialogue, next_field, draft).await?;
+        app.bot
+            .send_html_message(response, get_keyboard_for_field(next_field))
+            .await?;
+    } else {
+        // Final step - go to confirmation
+        enter_confirm_save_listing(app, dialogue, draft, None).await?;
+    }
+    Ok(())
+}
+
+/// Handle text input for field editing
+pub async fn handle_editing_field_input(
+    app: App,
+    dialogue: RootDialogue,
+    field: ListingField,
+    mut draft: ListingDraft,
+    msg: Message,
+) -> BotResult {
+    info!("User editing field {field:?}");
+
+    // Process the field update
+    match update_field_on_draft(field, &mut draft, msg.text()) {
+        Ok(()) => (),
+        Err(SetFieldError::ValidationFailed(e)) => {
+            return Err(BotError::user_visible(e));
+        }
+        Err(SetFieldError::UnsupportedFieldForListingType) => {
+            return Err(anyhow!("Cannot update field {field:?} for listing type").into());
+        }
+        Err(SetFieldError::FieldRequired) => {
+            return Err(anyhow!("Cannot update field {field:?} on existing listing").into());
+        }
+    };
+
+    let flash = get_edit_success_message(field, draft.listing_type());
+    enter_edit_listing_draft(app, draft, dialogue, Some(flash)).await?;
+    Ok(())
+}
+
+/// Handle viewing draft confirmation callbacks
+pub async fn handle_viewing_draft_callback(
+    app: App,
+    dialogue: RootDialogue,
+    draft: ListingDraft,
+    user: PersistedUser,
+    callback_query: CallbackQuery,
+) -> BotResult {
+    let data = extract_callback_data(&app.bot, callback_query).await?;
+
+    match ConfirmationKeyboardButtons::try_from(data.as_str())? {
+        ConfirmationKeyboardButtons::Create | ConfirmationKeyboardButtons::Save => {
+            info!("User confirmed listing creation");
+            let success_message = save_listing(&app.daos.listing, draft).await?;
+            enter_my_listings(app, dialogue, user, Some(success_message)).await?;
+        }
+        ConfirmationKeyboardButtons::Cancel => {
+            info!("User cancelled listing update");
+            let response = "🗑️ <b>Changes Discarded</b>\n\n\
+                    Your changes have been discarded and not saved."
+                .to_string();
+            app.bot.send_html_message(response, None).await?;
+            dialogue.exit().await.context("failed to exit dialogue")?;
+        }
+        ConfirmationKeyboardButtons::Discard => {
+            info!("User discarded listing creation");
+
+            let response = "🗑️ <b>Listing Discarded</b>\n\n\
+                    Your listing has been discarded and not created.\n\
+                    You can start a new listing anytime with /newlisting."
+                .to_string();
+            app.bot.send_html_message(response, None).await?;
+            dialogue.exit().await.context("failed to exit dialogue")?;
+        }
+        ConfirmationKeyboardButtons::Edit => {
+            info!("User chose to edit listing");
+            enter_edit_listing_draft(app, draft, dialogue, None).await?;
+        }
+    }
+
+    Ok(())
+}
+
+/// Handle editing draft field selection callbacks
+pub async fn handle_editing_draft_callback(
+    app: App,
+    draft: ListingDraft,
+    dialogue: RootDialogue,
+    callback_query: CallbackQuery,
+) -> BotResult {
+    let data = extract_callback_data(&app.bot, callback_query).await?;
+    info!("User in editing screen, showing field selection");
+
+    let button = FieldSelectionKeyboardButtons::try_from(data.as_str())?;
+    if button == FieldSelectionKeyboardButtons::Done {
+        return enter_confirm_save_listing(app, dialogue, draft, None).await;
+    }
+
+    let field = match button {
+        FieldSelectionKeyboardButtons::Title => ListingField::Title,
+        FieldSelectionKeyboardButtons::Description => ListingField::Description,
+        FieldSelectionKeyboardButtons::Price => ListingField::Price,
+        FieldSelectionKeyboardButtons::Slots => ListingField::Slots,
+        FieldSelectionKeyboardButtons::StartTime => ListingField::StartTime,
+        FieldSelectionKeyboardButtons::Duration => ListingField::EndTime,
+        FieldSelectionKeyboardButtons::Done => {
+            return Err(anyhow::anyhow!("Done button should not be used here").into());
+        }
+    };
+
+    let value = get_current_field_value(&draft, field)?;
+    let keyboard = get_edit_keyboard_for_field(field);
+
+    dialogue
+        .update(DialogueRootState::NewListing(
+            NewListingState::EditingDraftField { field, draft },
+        ))
+        .await
+        .context("failed to update dialogue")?;
+
+    let response = format!("Editing {field:?}\n\nPrevious value: {value}");
+    app.bot.send_html_message(response, Some(keyboard)).await?;
+
+    Ok(())
+}
+
+/// Handle editing draft field callbacks (back button, etc.)
+pub async fn handle_editing_draft_field_callback(
+    app: App,
+    dialogue: RootDialogue,
+    field: ListingField,
+    draft: ListingDraft,
+    callback_query: CallbackQuery,
+) -> BotResult {
+    let data = extract_callback_data(&app.bot, callback_query).await?;
+    info!("User editing field: {field:?} -> {data:?}");
+
+    if data == "edit_back" {
+        enter_edit_listing_draft(app, draft, dialogue, None).await?;
+        return Ok(());
+    }
+
+    // This callback handler typically receives button presses, not text input
+    // For now, just redirect back to edit screen since callback data isn't suitable for validation
+    enter_edit_listing_draft(app, draft, dialogue, None).await?;
+
+    Ok(())
+}
+
+/// Enter the edit listing draft screen
+pub async fn enter_edit_listing_draft(
+    app: App,
+    draft: ListingDraft,
+    dialogue: RootDialogue,
+    flash_message: Option<String>,
+) -> BotResult {
+    display_listing_summary(
+        app,
+        &draft,
+        Some(FieldSelectionKeyboardButtons::to_keyboard()),
+        flash_message,
+    )
+    .await?;
+    dialogue
+        .update(NewListingState::EditingDraft(draft))
+        .await
+        .context("failed to update dialogue")?;
+
+    Ok(())
+}
+
+/// Save the listing to the database
+async fn save_listing(listing_dao: &ListingDAO, draft: ListingDraft) -> BotResult<String> {
+    let (listing, success_message) = if let Some(fields) = draft.persisted {
+        let listing = listing_dao
+            .update_listing(&PersistedListing {
+                persisted: fields,
+                base: draft.base,
+                fields: draft.fields,
+            })
+            .await?;
+        (listing, "Listing updated!")
+    } else {
+        let listing = listing_dao
+            .insert_listing(&NewListing {
+                persisted: (),
+                base: draft.base,
+                fields: draft.fields,
+            })
+            .await?;
+        (listing, "Listing created!")
+    };
+
+    Ok(format!("✅ {success_message}: {}", listing.base.title))
+}
+
+/// Get the current value of a field for display
+fn get_current_field_value(
+    draft: &ListingDraft,
+    field: ListingField,
+) -> Result<String, anyhow::Error> {
+    let step = step_for_field(field, draft.listing_type())
+        .ok_or_else(|| anyhow::anyhow!("Cannot get field value for field {field:?}"))?;
+    match (step.get_field_value)(draft) {
+        Ok(value) => Ok(value.unwrap_or_else(|| "(none)".to_string())),
+        Err(e) => Err(anyhow::anyhow!(
+            "Cannot get field value for field {field:?}: {e:?}"
+        )),
+    }
+}
+
+/// Get the edit keyboard for a field
+fn get_edit_keyboard_for_field(field: ListingField) -> InlineKeyboardMarkup {
+    use crate::message_utils::create_single_button_keyboard;
+
+    let back_button = create_single_button_keyboard("🔙 Back", "edit_back");
+
+    match field {
+        ListingField::Description => {
+            let clear_button =
+                create_single_button_keyboard("🧹 Clear description", "edit_clear_description");
+            back_button.append_row(clear_button.inline_keyboard[0].clone())
+        }
+        ListingField::Slots => {
+            back_button.append_row(SlotsKeyboardButtons::to_keyboard().inline_keyboard[0].clone())
+        }
+        ListingField::StartTime => back_button
+            .append_row(StartTimeKeyboardButtons::to_keyboard().inline_keyboard[0].clone()),
+        ListingField::EndTime => back_button
+            .append_row(DurationKeyboardButtons::to_keyboard().inline_keyboard[0].clone()),
+        _ => back_button,
+    }
+}
--- a/src/commands/new_listing/keyboard.rs
+++ b/src/commands/new_listing/keyboard.rs
@@ -1,5 +1,26 @@
 use crate::keyboard_buttons;

+keyboard_buttons! {
+    pub enum NavKeyboardButtons {
+        Back("⬅️ Back", "back"),
+        Skip("⏭️ Skip", "skip"),
+        Cancel("❌ Cancel", "cancel"),
+    }
+}
+
+keyboard_buttons! {
+    pub enum CurrencyTypeKeyboardButtons {
+        [
+            Usd("🇺🇸 USD", "currency_type_usd"),
+            Cad("🇨🇦 CAD", "currency_type_cad"),
+        ],
+        [
+            Gbp("🇬🇧 GBP", "currency_type_gbp"),
+            Eur("🇪🇺 EUR", "currency_type_eur"),
+        ],
+    }
+}
+
 keyboard_buttons! {
    pub enum DurationKeyboardButtons {
        OneDay("1 day", "duration_1_day"),
@@ -20,9 +41,11 @@ keyboard_buttons! {

 keyboard_buttons! {
    pub enum ConfirmationKeyboardButtons {
+        Save("✅ Save", "confirm_save"),
        Create("✅ Create", "confirm_create"),
        Edit("✏️ Edit", "confirm_edit"),
        Discard("🗑️ Discard", "confirm_discard"),
+        Cancel("❌ Cancel", "confirm_cancel"),
    }
 }

@@ -42,7 +65,7 @@ keyboard_buttons! {
        ],
        [
            Done("✅ Done", "edit_done"),
-        ]
+        ],
    }
 }

@@ -51,3 +74,24 @@ keyboard_buttons! {
        Now("Now", "start_time_now"),
    }
 }
+
+keyboard_buttons! {
+    pub enum ListingTypeKeyboardButtons {
+        [
+            FixedPrice("🛍️ Fixed Price", "listing_type_fixed_price"),
+            BasicAuction("⏰ Basic Auction", "listing_type_basic_auction"),
+        ],
+        [
+            BlindAuction("🎭 Blind Auction", "listing_type_blind_auction"),
+            MultiSlot("🎯 Multi-Slot Auction", "listing_type_multi_slot"),
+        ]
+    }
+}
+
+keyboard_buttons! {
+    pub enum EditMinimumBidIncrementKeyboardButtons {
+        OneDollar("$1.00", "edit_minimum_bid_increment_1_00"),
+        FiveDollars("$5.00", "edit_minimum_bid_increment_5_00"),
+        TenDollars("$10.00", "edit_minimum_bid_increment_10_00"),
+    }
+}
--- a/src/commands/new_listing/messages.rs
+++ b/src/commands/new_listing/messages.rs
@@ -0,0 +1,371 @@
+//! Message constants and generation functions for the new listing wizard
+//!
+//! This module centralizes all user-facing messages to eliminate duplication
+//! and provide a single source of truth for wizard text.
+
+use crate::commands::new_listing::types::ListingField;
+use crate::commands::new_listing::validations::*;
+use crate::commands::new_listing::{keyboard::*, ListingDraft};
+use crate::db::listing::ListingFields;
+use crate::db::ListingType;
+use crate::message_utils::format_datetime;
+use teloxide::types::InlineKeyboardMarkup;
+
+#[derive(Debug)]
+pub enum GetFieldError {
+    UnsupportedListingType,
+}
+pub type GetFieldResult<T> = Result<Option<T>, GetFieldError>;
+
+#[derive(Copy, Clone)]
+pub struct ListingStepData {
+    pub field_type: ListingField,
+    pub field_name: &'static str,
+    pub description: &'static [&'static str],
+    pub get_field_value: fn(&ListingDraft) -> GetFieldResult<String>,
+    pub set_field_value: fn(&mut ListingDraft, Option<String>) -> Result<(), SetFieldError>,
+}
+
+macro_rules! get_field_mut {
+    ($fields:expr, $($variant:ident { $field:ident }),+) => {
+        match &mut $fields {
+            $(
+                get_field_mut!(@field_name $variant fields) => &mut fields.$field,
+            )+
+            _ => return Err(SetFieldError::UnsupportedFieldForListingType),
+        }
+    };
+    (@field_name BasicAuctionFields $f:ident) => { ListingFields::BasicAuction($f) };
+    (@field_name MultiSlotAuctionFields $f:ident) => { ListingFields::MultiSlotAuction($f) };
+    (@field_name FixedPriceListingFields $f:ident) => { ListingFields::FixedPriceListing($f) };
+    (@field_name BlindAuctionFields $f:ident) => { ListingFields::BlindAuction($f) };
+}
+
+macro_rules! get_field {
+    ($fields:expr, $($variant:ident { $field:ident }),+) => {
+        match &$fields {
+            $(
+                get_field!(@field_name $variant fields) => Ok(fields.$field),
+            )+
+            _ => Err(GetFieldError::UnsupportedListingType),
+        }
+    };
+    (@field_name BasicAuctionFields $f:ident) => { ListingFields::BasicAuction($f) };
+    (@field_name MultiSlotAuctionFields $f:ident) => { ListingFields::MultiSlotAuction($f) };
+    (@field_name FixedPriceListingFields $f:ident) => { ListingFields::FixedPriceListing($f) };
+    (@field_name BlindAuctionFields $f:ident) => { ListingFields::BlindAuction($f) };
+}
+
+const TITLE_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::Title,
+    field_name: "Title",
+    description: &["Please enter a title for your listing (max 100 characters)"],
+    get_field_value: |draft| Ok(Some(draft.base.title.clone())),
+    set_field_value: |draft, value| {
+        draft.base.title = require_field(value).and_then(validate_title)?;
+        Ok(())
+    },
+};
+
+const DESCRIPTION_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::Description,
+    field_name: "Description",
+    description: &["Please enter a description for your listing (optional)"],
+    get_field_value: |draft| Ok(draft.base.description.clone()),
+    set_field_value: |draft, value| {
+        draft.base.description = value.map(validate_description).transpose()?;
+        Ok(())
+    },
+};
+
+const CURRENCY_TYPE_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::CurrencyType,
+    field_name: "Currency Type",
+    description: &["Please enter the currency type for your listing (optional)"],
+    get_field_value: |draft| Ok(Some(draft.base.currency_type.to_string())),
+    set_field_value: |draft, value| {
+        draft.base.currency_type = require_field(value).and_then(validate_currency_type)?;
+        Ok(())
+    },
+};
+
+const START_TIME_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::StartTime,
+    field_name: "Start Time",
+    description: &[
+        "When should your listing start?",
+        "• Click 'Now' to start immediately",
+        "• Enter duration to delay (e.g., '2 days' for 2 days from now, '1 hour' for 1 hour from now)",
+        "• Maximum delay: 168 hours (7 days)",
+    ],
+    get_field_value: |draft| {
+        Ok(Some(format_datetime(draft.base.starts_at)))
+    },
+    set_field_value: |draft, value| {
+        draft.base.starts_at = require_field(value).and_then(validate_start_time)?;
+        Ok(())
+    },
+};
+
+const DURATION_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::EndTime,
+    field_name: "End Time",
+    description: &[
+        "When should your listing end?",
+        "• Enter duration in hours (minimum 1 hour, maximum 720 hours / 30 days):",
+    ],
+    get_field_value: |draft| Ok(Some(format_datetime(draft.base.ends_at))),
+    set_field_value: |draft, value| {
+        draft.base.ends_at =
+            draft.base.starts_at + require_field(value).and_then(validate_duration)?;
+        Ok(())
+    },
+};
+
+const PRICE_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::Price,
+    field_name: "Price",
+    description: &[
+        "Please enter the fixed price for your listing (e.g., 10.50, 25, 0.99)",
+        "• Price should be in USD",
+    ],
+    get_field_value: |draft| {
+        let buy_now_price = get_field!(draft.fields, FixedPriceListingFields { buy_now_price })?;
+        Ok(Some(format!("${buy_now_price}")))
+    },
+    set_field_value: |draft, value| {
+        *get_field_mut!(draft.fields, FixedPriceListingFields { buy_now_price }) =
+            require_field(value).and_then(validate_price)?;
+        Ok(())
+    },
+};
+
+const SLOTS_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::Slots,
+    field_name: "Slots",
+    description: &[
+        "How many items are available for sale?",
+        "• Choose a common value below or enter a custom number (1-1000)",
+    ],
+    get_field_value: |draft| {
+        let slots_available =
+            get_field!(draft.fields, FixedPriceListingFields { slots_available })?;
+        Ok(Some(format!("{slots_available} slots")))
+    },
+    set_field_value: |draft, value| {
+        *get_field_mut!(draft.fields, FixedPriceListingFields { slots_available }) =
+            require_field(value).and_then(validate_slots)?;
+        Ok(())
+    },
+};
+
+const STARTING_BID_AMOUNT_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::StartingBidAmount,
+    field_name: "Starting Bid Amount",
+    description: &[
+        "Please enter the starting bid amount for your auction (e.g., 10.50, 25, 0.99):",
+        "• Starting bid should be in USD",
+    ],
+    get_field_value: |draft| {
+        let starting_bid_amount = get_field!(draft.fields, BasicAuctionFields { starting_bid })?;
+        Ok(Some(format!("${starting_bid_amount}")))
+    },
+    set_field_value: |draft, value| {
+        *get_field_mut!(draft.fields, BasicAuctionFields { starting_bid }) =
+            require_field(value).and_then(validate_price)?;
+        Ok(())
+    },
+};
+
+const BUY_NOW_PRICE_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::BuyNowPrice,
+    field_name: "Buy Now Price",
+    description: &[
+        "Please enter the buy now price for your auction (e.g., 10.50, 25, 0.99):",
+        "• Buy now price should be in USD",
+    ],
+    get_field_value: |draft| {
+        let buy_now_price = get_field!(draft.fields, BasicAuctionFields { buy_now_price })?;
+        Ok(buy_now_price.map(|price| format!("${price}")))
+    },
+    set_field_value: |draft, value| {
+        *get_field_mut!(draft.fields, BasicAuctionFields { buy_now_price }) =
+            value.map(validate_price).transpose()?;
+        Ok(())
+    },
+};
+
+const BID_INCREMENT_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::MinBidIncrement,
+    field_name: "Minimum Bid Increment",
+    description: &[
+        "Please enter the minimum bid increment for your auction (e.g., 10.50, 25, 0.99):",
+        "• Default: $1.00",
+        "• Minimum bid increment should be in USD",
+    ],
+    get_field_value: |draft| {
+        let min_bid_increment = get_field!(draft.fields, BasicAuctionFields { min_increment })?;
+        Ok(Some(format!("${min_bid_increment}")))
+    },
+    set_field_value: |draft, value| {
+        *get_field_mut!(draft.fields, BasicAuctionFields { min_increment }) =
+            require_field(value).and_then(validate_price)?;
+        Ok(())
+    },
+};
+
+const ANTI_SNIPE_MINUTES_LISTING_STEP_DATA: ListingStepData = ListingStepData {
+    field_type: ListingField::AntiSnipeMinutes,
+    field_name: "Anti-Snipe Minutes",
+    description: &[
+        "Please enter the anti-snipe minutes for your auction (e.g., 10, 15, 20):",
+        "• Default: 5 minutes",
+        "• Anti-snipe will extend the auction duration by the number of minutes entered",
+        "• Anti-snipe minutes should be in minutes",
+    ],
+    get_field_value: |draft| {
+        let anti_snipe_minutes =
+            get_field!(draft.fields, BasicAuctionFields { anti_snipe_minutes })?;
+        Ok(anti_snipe_minutes.map(|minutes| format!("{minutes} minutes")))
+    },
+    set_field_value: |draft, value| {
+        *get_field_mut!(draft.fields, BasicAuctionFields { anti_snipe_minutes }) =
+            value.map(validate_anti_snipe_minutes).transpose()?;
+        Ok(())
+    },
+};
+
+const FIXED_PRICE_LISTING_STEPS: &[ListingStepData] = &[
+    TITLE_LISTING_STEP_DATA,
+    DESCRIPTION_LISTING_STEP_DATA,
+    CURRENCY_TYPE_LISTING_STEP_DATA,
+    PRICE_LISTING_STEP_DATA,
+    SLOTS_LISTING_STEP_DATA,
+    START_TIME_LISTING_STEP_DATA,
+    DURATION_LISTING_STEP_DATA,
+];
+
+const BASIC_AUCTION_STEPS: &[ListingStepData] = &[
+    TITLE_LISTING_STEP_DATA,
+    DESCRIPTION_LISTING_STEP_DATA,
+    CURRENCY_TYPE_LISTING_STEP_DATA,
+    STARTING_BID_AMOUNT_LISTING_STEP_DATA,
+    BUY_NOW_PRICE_LISTING_STEP_DATA,
+    BID_INCREMENT_LISTING_STEP_DATA,
+    ANTI_SNIPE_MINUTES_LISTING_STEP_DATA,
+    START_TIME_LISTING_STEP_DATA,
+    DURATION_LISTING_STEP_DATA,
+];
+
+const BLIND_AUCTION_STEPS: &[ListingStepData] = &[];
+const MULTI_SLOT_AUCTION_STEPS: &[ListingStepData] = &[];
+
+pub fn steps_for_listing_type(listing_type: ListingType) -> &'static [ListingStepData] {
+    match listing_type {
+        ListingType::FixedPriceListing => FIXED_PRICE_LISTING_STEPS,
+        ListingType::BasicAuction => BASIC_AUCTION_STEPS,
+        ListingType::BlindAuction => BLIND_AUCTION_STEPS,
+        ListingType::MultiSlotAuction => MULTI_SLOT_AUCTION_STEPS,
+    }
+}
+
+fn get_step_number(field: ListingField, listing_type: ListingType) -> Option<usize> {
+    let steps = steps_for_listing_type(listing_type);
+    steps.iter().position(|step| step.field_type == field)
+}
+
+fn get_total_steps(listing_type: ListingType) -> usize {
+    steps_for_listing_type(listing_type).len()
+}
+
+pub fn step_for_field(
+    field: ListingField,
+    listing_type: ListingType,
+) -> Option<&'static ListingStepData> {
+    steps_for_listing_type(listing_type)
+        .iter()
+        .find(|step| step.field_type == field)
+}
+
+/// Get the next field in the wizard sequence
+pub fn get_next_field(field: ListingField, listing_type: ListingType) -> Option<ListingField> {
+    let idx = get_step_number(field, listing_type)?;
+    let total_steps = get_total_steps(listing_type);
+    if idx + 1 >= total_steps {
+        return None;
+    }
+    Some(steps_for_listing_type(listing_type)[idx + 1].field_type)
+}
+
+/// Get the step instruction message for a field
+pub fn get_step_message(field: ListingField, listing_type: ListingType) -> String {
+    let step = step_for_field(field, listing_type).unwrap();
+    let setp_number = get_step_number(field, listing_type).unwrap() + 1;
+    let total_steps = get_total_steps(listing_type);
+    let description = step.description.join("\n");
+    format!("<i>Step {setp_number} / {total_steps}</i>: {description}")
+}
+
+/// Get the success message for completing a field
+pub fn get_success_message(field: ListingField, listing_type: ListingType) -> String {
+    let step = step_for_field(field, listing_type).unwrap();
+    let field_name = step.field_name;
+    format!("✅ {field_name} saved!")
+}
+
+/// Get the success message for editing a field
+pub fn get_edit_success_message(field: ListingField, listing_type: ListingType) -> String {
+    let step = step_for_field(field, listing_type).unwrap();
+    let field_name = step.field_name;
+    format!("✅ {field_name} updated!")
+}
+
+pub fn get_field_name(field: ListingField, listing_type: ListingType) -> String {
+    let step = step_for_field(field, listing_type).unwrap();
+    step.field_name.to_string()
+}
+
+/// Get the appropriate keyboard for a field
+pub fn get_keyboard_for_field(field: ListingField) -> Option<InlineKeyboardMarkup> {
+    match field {
+        ListingField::Title => Some(InlineKeyboardMarkup::new([[
+            NavKeyboardButtons::Back.to_button()
+        ]])),
+        ListingField::Description => Some(InlineKeyboardMarkup::new([[
+            NavKeyboardButtons::Back.to_button(),
+            NavKeyboardButtons::Skip.to_button(),
+        ]])),
+        ListingField::CurrencyType => Some(CurrencyTypeKeyboardButtons::to_keyboard()),
+        ListingField::Price => None,
+        ListingField::Slots => Some(SlotsKeyboardButtons::to_keyboard()),
+        ListingField::StartTime => Some(StartTimeKeyboardButtons::to_keyboard()),
+        ListingField::EndTime => Some(DurationKeyboardButtons::to_keyboard()),
+        // TODO - Add keyboards for these fields
+        ListingField::StartingBidAmount => None,
+        ListingField::BuyNowPrice => Some(InlineKeyboardMarkup::new([[
+            NavKeyboardButtons::Skip.to_button()
+        ]])),
+        ListingField::MinBidIncrement => Some(
+            EditMinimumBidIncrementKeyboardButtons::to_keyboard()
+                .append_row([NavKeyboardButtons::Skip.to_button()]),
+        ),
+        ListingField::AntiSnipeMinutes => Some(InlineKeyboardMarkup::new([[
+            NavKeyboardButtons::Skip.to_button(),
+        ]])),
+    }
+}
+
+/// Get the listing type selection message
+pub fn get_listing_type_selection_message() -> &'static str {
+    "🛍️ <b>What type of listing would you like to create?</b>\n\n\
+    <b>🛍️ Fixed Price:</b> Set a fixed price for immediate purchase\n\
+    <b>⏰ Basic Auction:</b> Traditional time-based auction with bidding\n\
+    <b>🎭 Blind Auction:</b> Buyers submit sealed bids, you choose the winner\n\
+    <b>🎯 Multi-Slot Auction:</b> Multiple items/winners in one auction\n\n\
+    Choose your listing type:"
+}
+
+/// Get the keyboard for listing type selection
+pub fn get_listing_type_keyboard() -> InlineKeyboardMarkup {
+    ListingTypeKeyboardButtons::to_keyboard().append_row([NavKeyboardButtons::Back.to_button()])
+}
--- a/src/commands/new_listing/mod.rs
+++ b/src/commands/new_listing/mod.rs
--- a/src/commands/new_listing/tests.rs
+++ b/src/commands/new_listing/tests.rs
@@ -0,0 +1,132 @@
+use std::str::FromStr;
+
+use chrono::Duration;
+
+use crate::{
+    assert_timestamps_approx_eq,
+    commands::new_listing::{
+        field_processing::update_field_on_draft,
+        types::{ListingDraft, ListingField},
+    },
+    db::{
+        listing::{FixedPriceListingFields, ListingFields},
+        CurrencyType, DbUserId, MoneyAmount,
+    },
+};
+
+fn create_test_draft() -> ListingDraft {
+    ListingDraft {
+        has_changes: false,
+        persisted: None,
+        base: crate::db::listing::ListingBase {
+            seller_id: DbUserId::new(1),
+            title: "".to_string(),
+            description: None,
+            currency_type: CurrencyType::Usd,
+            starts_at: chrono::Utc::now(),
+            ends_at: chrono::Utc::now() + chrono::Duration::hours(1),
+            is_active: true,
+        },
+        fields: ListingFields::FixedPriceListing(FixedPriceListingFields {
+            buy_now_price: MoneyAmount::default(),
+            slots_available: 0,
+        }),
+    }
+}
+
+// === Business Logic Tests ===
+
+#[test]
+fn test_complete_field_processing_workflow() {
+    let mut draft = create_test_draft();
+
+    // Process all fields in sequence with realistic inputs
+    let workflow = [
+        (ListingField::Title, "Handcrafted Wooden Bowl"),
+        (
+            ListingField::Description,
+            "Beautiful handmade oak bowl, perfect for serving",
+        ),
+        (ListingField::Price, "34.99"),
+        (ListingField::Slots, "2"),
+        (ListingField::StartTime, "1 hour"),
+        (ListingField::EndTime, "3 days"),
+    ];
+
+    for (field, input) in workflow {
+        let result = update_field_on_draft(field, &mut draft, Some(input));
+        assert!(result.is_ok(), "Processing {field:?} should succeed");
+    }
+
+    // Verify realistic final state
+    assert_eq!(draft.base.title, "Handcrafted Wooden Bowl");
+    assert!(draft
+        .base
+        .description
+        .as_ref()
+        .unwrap()
+        .contains("oak bowl"));
+
+    if let ListingFields::FixedPriceListing(fields) = &draft.fields {
+        assert_eq!(
+            fields.buy_now_price,
+            MoneyAmount::from_str("34.99").unwrap()
+        );
+        assert_eq!(fields.slots_available, 2);
+    }
+
+    assert_timestamps_approx_eq!(
+        draft.base.starts_at,
+        chrono::Utc::now() + Duration::hours(1),
+        Duration::milliseconds(100)
+    );
+    assert_timestamps_approx_eq!(
+        draft.base.ends_at,
+        chrono::Utc::now() + Duration::hours(72) + Duration::hours(1),
+        Duration::milliseconds(100)
+    );
+}
+
+#[test]
+fn test_natural_language_duration_conversion() {
+    let mut draft = create_test_draft();
+
+    // Test critical natural language parsing works in business context
+    let business_durations = [
+        ("1 day", 24),    // Common short listing
+        ("7 days", 168),  // Standard week-long listing
+        ("30 days", 720), // Maximum allowed duration
+    ];
+
+    for (input, expected_hours) in business_durations {
+        update_field_on_draft(ListingField::EndTime, &mut draft, Some(input)).unwrap();
+
+        assert_timestamps_approx_eq!(
+            draft.base.ends_at,
+            chrono::Utc::now() + chrono::Duration::hours(expected_hours),
+            Duration::milliseconds(100),
+            "Business duration '{input}' should convert correctly"
+        );
+    }
+}
+
+#[test]
+fn test_price_and_slots_consistency_for_fixed_price_listings() {
+    let mut draft = create_test_draft();
+
+    // Test that price and slots work together correctly for business logic
+    update_field_on_draft(ListingField::Price, &mut draft, Some("25.00")).unwrap();
+    update_field_on_draft(ListingField::Slots, &mut draft, Some("5")).unwrap();
+
+    if let ListingFields::FixedPriceListing(fields) = &draft.fields {
+        assert_eq!(
+            fields.buy_now_price,
+            MoneyAmount::from_str("25.00").unwrap()
+        );
+        assert_eq!(fields.slots_available, 5);
+
+        // Business logic: Total potential value is price * slots
+        let total_value = fields.buy_now_price.cents() * fields.slots_available as i64;
+        assert_eq!(total_value, 12500); // $25.00 * 5 = $125.00 (12500 cents)
+    }
+}
--- a/src/commands/new_listing/types.rs
+++ b/src/commands/new_listing/types.rs
@@ -1,32 +1,102 @@
 use crate::{
-    db::{ListingDuration, MoneyAmount},
+    db::{
+        listing::{
+            BasicAuctionFields, BlindAuctionFields, FixedPriceListingFields, ListingBase,
+            ListingFields, MultiSlotAuctionFields, PersistedListing, PersistedListingFields,
+        },
+        CurrencyType, DbUserId, ListingType, MoneyAmount,
+    },
    DialogueRootState,
 };
+use chrono::{Duration, Utc};
 use serde::{Deserialize, Serialize};

-#[derive(Debug, Clone, Eq, PartialEq, Serialize, Deserialize, Default)]
+#[derive(Debug, Clone, Eq, PartialEq, Serialize, Deserialize)]
 pub struct ListingDraft {
-    pub title: String,
-    pub description: Option<String>,
-    pub buy_now_price: MoneyAmount,
-    pub slots_available: i32,
-    pub start_delay: ListingDuration,
-    pub duration: ListingDuration,
+    pub has_changes: bool,
+    pub persisted: Option<PersistedListingFields>,
+    pub base: ListingBase,
+    pub fields: ListingFields,
+}
+
+impl ListingDraft {
+    pub fn new_for_seller_with_type(seller_id: DbUserId, listing_type: ListingType) -> Self {
+        let fields = match listing_type {
+            ListingType::BasicAuction => ListingFields::BasicAuction(BasicAuctionFields {
+                starting_bid: MoneyAmount::default(),
+                buy_now_price: None,
+                min_increment: MoneyAmount::from_cents(100), // Default $1.00 increment
+                anti_snipe_minutes: Some(5),
+            }),
+            ListingType::MultiSlotAuction => {
+                ListingFields::MultiSlotAuction(MultiSlotAuctionFields {
+                    starting_bid: MoneyAmount::default(),
+                    buy_now_price: MoneyAmount::default(),
+                    min_increment: Some(MoneyAmount::from_cents(100)), // Default $1.00 increment
+                    slots_available: 1,
+                    anti_snipe_minutes: 5,
+                })
+            }
+            ListingType::FixedPriceListing => {
+                ListingFields::FixedPriceListing(FixedPriceListingFields {
+                    buy_now_price: MoneyAmount::default(),
+                    slots_available: 1,
+                })
+            }
+            ListingType::BlindAuction => ListingFields::BlindAuction(BlindAuctionFields {
+                starting_bid: MoneyAmount::default(),
+            }),
+        };
+
+        Self {
+            has_changes: false,
+            persisted: None,
+            base: ListingBase {
+                seller_id,
+                currency_type: CurrencyType::Usd,
+                title: "".to_string(),
+                description: None,
+                starts_at: Utc::now(),
+                ends_at: Utc::now() + Duration::days(3),
+                is_active: true,
+            },
+            fields,
+        }
+    }
+
+    pub fn from_persisted(listing: PersistedListing) -> Self {
+        Self {
+            has_changes: false,
+            persisted: Some(listing.persisted),
+            base: listing.base,
+            fields: listing.fields,
+        }
+    }
+
+    pub fn listing_type(&self) -> ListingType {
+        (&self.fields).into()
+    }
 }

 #[derive(Copy, Clone, Serialize, Deserialize, PartialEq, Eq, Debug)]
 pub enum ListingField {
    Title,
    Description,
+    CurrencyType,
    Price,
    Slots,
    StartTime,
-    Duration,
+    EndTime,
+    StartingBidAmount,
+    BuyNowPrice,
+    MinBidIncrement,
+    AntiSnipeMinutes,
 }

 // Dialogue state for the new listing wizard
 #[derive(Debug, Clone, Eq, PartialEq, Serialize, Deserialize)]
 pub enum NewListingState {
+    SelectingListingType,
    AwaitingDraftField {
        field: ListingField,
        draft: ListingDraft,
--- a/src/commands/new_listing/ui.rs
+++ b/src/commands/new_listing/ui.rs
@@ -0,0 +1,85 @@
+//! UI display functions for the new listing wizard
+//!
+//! This module handles all user interface display logic including
+//! listing summaries, confirmation screens, and edit interfaces.
+
+use crate::commands::new_listing::keyboard::ConfirmationKeyboardButtons;
+use crate::commands::new_listing::messages::steps_for_listing_type;
+use crate::commands::new_listing::NewListingState;
+use crate::db::ListingType;
+use crate::App;
+use crate::RootDialogue;
+use crate::{commands::new_listing::types::ListingDraft, BotResult};
+use anyhow::Context;
+use teloxide::types::InlineKeyboardMarkup;
+
+/// Display the listing summary with optional flash message and keyboard
+pub async fn display_listing_summary(
+    app: App,
+    draft: &ListingDraft,
+    keyboard: Option<InlineKeyboardMarkup>,
+    flash_message: Option<String>,
+) -> BotResult {
+    let mut response_lines = vec![];
+    let listing_type: ListingType = (&draft.fields).into();
+
+    if let Some(flash_message) = flash_message {
+        response_lines.push(flash_message.to_string());
+    }
+
+    let unsaved_changes = if draft.has_changes {
+        "<i>Unsaved changes</i>"
+    } else {
+        ""
+    };
+    response_lines.push(format!(
+        "📋 <b>{listing_type} Summary</b> {unsaved_changes}"
+    ));
+    response_lines.push("".to_string());
+
+    for step in steps_for_listing_type(listing_type) {
+        let field_value = match (step.get_field_value)(draft) {
+            Ok(value) => value.unwrap_or_else(|| "(none)".to_string()),
+            Err(_) => continue,
+        };
+        response_lines.push(format!("<b>{}:</b> {}", step.field_name, field_value));
+    }
+
+    response_lines.push("".to_string());
+    response_lines.push("Edit your listing:".to_string());
+
+    app.bot
+        .send_html_message(response_lines.join("\n"), keyboard)
+        .await?;
+
+    Ok(())
+}
+
+/// Show the final confirmation screen before creating/saving the listing
+pub async fn enter_confirm_save_listing(
+    app: App,
+    dialogue: RootDialogue,
+    draft: ListingDraft,
+    flash: Option<String>,
+) -> BotResult {
+    let keyboard = if draft.persisted.is_some() {
+        InlineKeyboardMarkup::default().append_row([
+            ConfirmationKeyboardButtons::Save.to_button(),
+            ConfirmationKeyboardButtons::Edit.to_button(),
+            ConfirmationKeyboardButtons::Discard.to_button(),
+        ])
+    } else {
+        InlineKeyboardMarkup::default().append_row([
+            ConfirmationKeyboardButtons::Create.to_button(),
+            ConfirmationKeyboardButtons::Edit.to_button(),
+            ConfirmationKeyboardButtons::Cancel.to_button(),
+        ])
+    };
+
+    display_listing_summary(app, &draft, Some(keyboard), flash).await?;
+    dialogue
+        .update(NewListingState::ViewingDraft(draft))
+        .await
+        .context("failed to update dialogue")?;
+    Ok(())
+}
--- a/src/commands/new_listing/validations.rs
+++ b/src/commands/new_listing/validations.rs
@@ -1,74 +1,179 @@
-use crate::db::{ListingDuration, MoneyAmount};
+use std::str::FromStr;
+
+use chrono::{DateTime, Duration, Utc};
+
+use crate::db::{CurrencyType, MoneyAmount};
+
+#[derive(Debug)]
+pub enum SetFieldError {
+    FieldRequired,
+    ValidationFailed(String),
+    UnsupportedFieldForListingType,
+}
+
+type SetFieldResult<T> = Result<T, SetFieldError>;
+
+fn validation_failed<T>(message: &str) -> SetFieldResult<T> {
+    Err(SetFieldError::ValidationFailed(message.to_string()))
+}
+macro_rules! validation_failed {
+    ($message:expr) => {
+        return validation_failed($message)
+    };
+}
+
+pub fn require_field(field: Option<String>) -> SetFieldResult<String> {
+    field.ok_or(SetFieldError::FieldRequired)
+}

 // Common input validation functions
-pub fn validate_title(text: &str) -> Result<String, String> {
+pub fn validate_title(text: impl AsRef<str>) -> SetFieldResult<String> {
+    let text = text.as_ref();
    if text.is_empty() {
-        return Err("❌ Title cannot be empty. Please enter a title for your listing:".to_string());
+        validation_failed!("❌ Title cannot be empty");
    }
    if text.len() > 100 {
-        return Err(
-            "❌ Title is too long (max 100 characters). Please enter a shorter title:".to_string(),
-        );
+        validation_failed!("❌ Title is too long (max 100 characters)");
    }
    Ok(text.to_string())
 }

-pub fn validate_description(text: &str) -> Result<String, String> {
+pub fn validate_description(text: impl AsRef<str>) -> SetFieldResult<String> {
+    let text = text.as_ref();
    if text.len() > 1000 {
-        return Err(
-            "❌ Description is too long (max 1000 characters). Please enter a shorter description:"
-                .to_string(),
-        );
+        validation_failed!("❌ Description is too long (max 1000 characters)");
    }
    Ok(text.to_string())
 }

-pub fn validate_price(text: &str) -> Result<MoneyAmount, String> {
+pub fn validate_currency_type(text: impl AsRef<str>) -> SetFieldResult<CurrencyType> {
+    let text = text.as_ref();
+    if let Ok(currency_type) = CurrencyType::try_from(text) {
+        Ok(currency_type)
+    } else {
+        validation_failed!("❌ Invalid currency type");
+    }
+}
+
+pub fn validate_price(text: impl AsRef<str>) -> SetFieldResult<MoneyAmount> {
+    let text = text.as_ref();
+
    match MoneyAmount::from_str(text) {
        Ok(amount) => {
            if amount.cents() <= 0 {
-                Err("❌ Price must be greater than $0.00. Please enter a valid price:".to_string())
+                validation_failed!("❌ Price must be greater than $0.00");
            } else {
                Ok(amount)
            }
        }
-        Err(_) => Err(
-            "❌ Invalid price format. Please enter a valid price (e.g., 10.50, 25, 0.99):"
-                .to_string(),
+        Err(_) => validation_failed!(
+            "❌ Invalid price format (use decimal format, e.g., 10.50, 25, 0.99):"
        ),
    }
 }

-pub fn validate_slots(text: &str) -> Result<i32, String> {
+pub fn validate_slots(text: impl AsRef<str>) -> SetFieldResult<i32> {
+    let text = text.as_ref();
    match text.parse::<i32>() {
        Ok(slots) if (1..=1000).contains(&slots) => Ok(slots),
-        Ok(_) => Err(
-            "❌ Number of slots must be between 1 and 1000. Please enter a valid number:"
-                .to_string(),
-        ),
-        Err(_) => Err("❌ Invalid number. Please enter a number from 1 to 1000:".to_string()),
+        Ok(_) => validation_failed!("❌ Number of slots must be between 1 and 1000"),
+        Err(_) => validation_failed!("❌ Invalid number. Please enter a number from 1 to 1000"),
    }
 }

-pub fn validate_duration(text: &str) -> Result<ListingDuration, String> {
-    match text.parse::<i32>() {
-        Ok(hours) if (1..=720).contains(&hours) => Ok(ListingDuration::hours(hours)), // 1 hour to 30 days
-        Ok(_) => Err(
-            "❌ Duration must be between 1 and 720 hours. Please enter a valid number:".to_string(),
-        ),
-        Err(_) => Err("❌ Invalid number. Please enter number of hours (1-720):".to_string()),
+pub fn validate_time(text: impl AsRef<str>, field_name: &str) -> SetFieldResult<Duration> {
+    let text = text.as_ref();
+    let text = text.trim().to_lowercase();
+
+    // Try to parse as plain number first (backwards compatibility)
+    if let Ok(hours) = text.parse::<i32>() {
+        if (1..=720).contains(&hours) {
+            return Ok(Duration::hours(hours as i64));
+        } else {
+            validation_failed!(&format!(
+                "❌ {field_name} must be between 1 hour and 30 days (720 hours)"
+            ));
+        }
+    }
+
+    // Parse natural language duration
+    let parts: Vec<&str> = text.split_whitespace().collect();
+    let (number_str, unit) = if parts.len() == 2 {
+        (parts[0], parts[1])
+    } else if parts.len() == 1 {
+        (text.as_str(), "hour")
+    } else {
+        validation_failed!(&format!(
+            "❌ Please enter {field_name} like '1 hour', '7 days', or just hours (1-720)"
+        ));
+    };
+
+    let number = match number_str.parse::<i32>() {
+        Ok(n) if n > 0 => n,
+        _ => validation_failed!(&format!(
+            "❌ {field_name} number must be a positive integer"
+        )),
+    };
+
+    let hours = match unit {
+        "hour" | "hours" | "hr" | "hrs" | "h" | "hs" => number,
+        "day" | "days" | "d" | "ds" => number * 24,
+        _ => validation_failed!("❌ Supported units: hour(s), day(s)"),
+    };
+
+    if (1..=720).contains(&hours) {
+        Ok(Duration::hours(hours as i64))
+    } else {
+        validation_failed!(&format!(
+            "❌ {field_name} must be between 1 hour and 30 days (720 hours)"
+        ));
    }
 }

-pub fn validate_start_time(text: &str) -> Result<ListingDuration, String> {
+pub fn validate_duration(text: impl AsRef<str>) -> SetFieldResult<Duration> {
+    validate_time(text, "Duration")
+}
+
+pub fn validate_start_time(text: impl AsRef<str>) -> SetFieldResult<DateTime<Utc>> {
+    validate_time(text, "Start Time").map(|duration| Utc::now() + duration)
+}
+
+pub fn validate_anti_snipe_minutes(text: impl AsRef<str>) -> SetFieldResult<i32> {
+    let text = text.as_ref();
    match text.parse::<i32>() {
-        Ok(hours) if (0..=168).contains(&hours) => Ok(ListingDuration::hours(hours)), // Max 1 week delay
-        Ok(_) => Err(
-            "❌ Start time must be between 0 and 168 hours. Please enter a valid number:"
-                .to_string(),
-        ),
-        Err(_) => Err(
-            "❌ Invalid number. Please enter number of hours (0 for immediate start):".to_string(),
-        ),
+        Ok(minutes) if (0..=1440).contains(&minutes) => Ok(minutes),
+        Ok(_) => validation_failed!("❌ Anti-snipe minutes must be between 0 and 1440"),
+        Err(_) => validation_failed!("❌ Invalid number. Please enter a number from 0 to 1440"),
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use rstest::rstest;
+
+    #[rstest]
+    #[case("24", Duration::hours(24))] // Plain number
+    #[case("1 hour", Duration::hours(1))]
+    #[case("2 hours", Duration::hours(2))]
+    #[case("1 day", Duration::hours(24))]
+    #[case("7 days", Duration::hours(168))]
+    #[case("30 days", Duration::hours(720))] // Max 30 days
+    fn test_validate_duration_valid(#[case] input: &str, #[case] expected: Duration) {
+        let result = validate_duration(input).unwrap();
+        assert_eq!(result, expected);
+    }
+
+    #[rstest]
+    #[case("0")]
+    #[case("0 hours")]
+    #[case("721")] // Over limit
+    #[case("1 week")] // Unsupported unit
+    #[case("1 month")] // Unsupported unit
+    #[case("1 year")] // Unsupported unit
+    #[case("abc")] // Invalid text
+    #[case("-1 hour")] // Negative
+    fn test_validate_duration_invalid(#[case] input: &str) {
+        assert!(validate_duration(input).is_err());
    }
 }
--- a/src/commands/settings.rs
+++ b/src/commands/settings.rs
@@ -1,16 +1,16 @@
+use crate::{App, BotResult};
 use log::info;
-use teloxide::{prelude::*, types::Message, Bot};
+use teloxide::types::Message;

-use crate::HandlerResult;
-
-pub async fn handle_settings(bot: Bot, msg: Message) -> HandlerResult {
+pub async fn handle_settings(app: App, msg: Message) -> BotResult {
    let response = "⚙️ Settings (Coming Soon)\n\n\
        Here you'll be able to configure:\n\
        • Notification preferences\n\
        • Language settings\n\
        • Default bid increments\n\
        • Outbid alerts\n\n\
-        Feature in development! 🛠️";
+        Feature in development! 🛠️"
+        .to_string();

    info!(
        "User {} ({}) accessed settings",
@@ -18,6 +18,6 @@ pub async fn handle_settings(bot: Bot, msg: Message) -> HandlerResult {
        msg.chat.id
    );

-    bot.send_message(msg.chat.id, response).await?;
+    app.bot.send_html_message(response, None).await?;
    Ok(())
 }
--- a/src/commands/start.rs
+++ b/src/commands/start.rs
@@ -1,24 +1,119 @@
+use anyhow::Context;
 use log::info;
-use teloxide::{prelude::*, types::Message, Bot};
+use teloxide::{
+    types::{CallbackQuery, Update},
+    utils::command::BotCommands,
+};

-use crate::HandlerResult;
+use crate::{
+    commands::my_listings::enter_my_listings, db::user::PersistedUser, keyboard_buttons,
+    message_utils::extract_callback_data, App, BotResult, Command, DialogueRootState, RootDialogue,
+};

-pub async fn handle_start(bot: Bot, msg: Message) -> HandlerResult {
-    let welcome_message = "🎯 Welcome to Pawctioneer Bot! 🎯\n\n\
-        This bot helps you participate in various types of auctions:\n\
-        • Standard auctions with anti-sniping protection\n\
-        • Multi-slot auctions (multiple winners)\n\
-        • Fixed price sales\n\
-        • Blind auctions\n\n\
-        Use /help to see all available commands.\n\n\
-        Ready to start your auction experience? 🚀";
+keyboard_buttons! {
+    pub enum MainMenuButtons {
+        [
+            MyListings("📋 My Listings", "menu_my_listings"),
+            MyBids("💰 My Bids", "menu_my_bids"),
+        ],
+        [
+            Settings("⚙️ Settings", "menu_settings"),
+            Help("❓ Help", "menu_help"),
+        ]
+    }
+}

-    info!(
-        "User {} ({}) started the bot",
-        msg.chat.username().unwrap_or("unknown"),
-        msg.chat.id
-    );
+/// Get the main menu welcome message
+fn get_main_menu_message() -> &'static str {
+    "🎯 <b>Welcome to Pawctioneer Bot!</b> 🎯\n\n\
+    This bot helps you participate in various types of auctions:\n\
+    • Standard auctions with anti-sniping protection\n\
+    • Multi-slot auctions (multiple winners)\n\
+    • Fixed price sales\n\
+    • Blind auctions\n\n\
+    Choose an option below to get started! 🚀"
+}
+
+pub async fn handle_start(app: App, dialogue: RootDialogue, update: Update) -> BotResult {
+    info!("got start message: {update:?}");
+    enter_main_menu(app, dialogue).await?;
+    Ok(())
+}
+
+/// Show the main menu with buttons
+pub async fn enter_main_menu(app: App, dialogue: RootDialogue) -> BotResult {
+    dialogue
+        .update(DialogueRootState::MainMenu)
+        .await
+        .context("failed to update dialogue")?;
+
+    app.bot
+        .send_html_message(
+            get_main_menu_message().to_string(),
+            Some(MainMenuButtons::to_keyboard()),
+        )
+        .await?;
+
+    Ok(())
+}
+
+pub async fn handle_main_menu_callback(
+    app: App,
+    dialogue: RootDialogue,
+    user: PersistedUser,
+    callback_query: CallbackQuery,
+) -> BotResult {
+    let data = extract_callback_data(&app.bot, callback_query).await?;
+    info!("User selected main menu option: {data:?}");
+
+    let button = MainMenuButtons::try_from(data.as_str())?;
+    match button {
+        MainMenuButtons::MyListings => {
+            // Call show_listings_for_user directly
+            enter_my_listings(app, dialogue, user, None).await?;
+        }
+        MainMenuButtons::MyBids => {
+            app.bot
+                .send_html_message(
+                    "💰 <b>My Bids (Coming Soon)</b>\n\n\
+                Here you'll be able to view:\n\
+                • Your active bids\n\
+                • Bid history\n\
+                • Won/lost auctions\n\
+                • Outbid notifications\n\n\
+                Feature in development! 🛠️"
+                        .to_string(),
+                    Some(MainMenuButtons::to_keyboard()),
+                )
+                .await?;
+        }
+        MainMenuButtons::Settings => {
+            app.bot
+                .send_html_message(
+                    "⚙️ <b>Settings (Coming Soon)</b>\n\n\
+                Here you'll be able to configure:\n\
+                • Notification preferences\n\
+                • Language settings\n\
+                • Default bid increments\n\
+                • Outbid alerts\n\n\
+                Feature in development! 🛠️"
+                        .to_string(),
+                    Some(MainMenuButtons::to_keyboard()),
+                )
+                .await?;
+        }
+        MainMenuButtons::Help => {
+            let help_message = format!(
+                "📋 <b>Available Commands:</b>\n\n{}\n\n\
+                📧 <b>Support:</b> Contact @admin for help\n\
+                🔗 <b>More info:</b> Use individual commands to get started!",
+                Command::descriptions()
+            );
+            app.bot
+                .send_html_message(help_message, Some(MainMenuButtons::to_keyboard()))
+                .await?;
+        }
+    }

-    bot.send_message(msg.chat.id, welcome_message).await?;
    Ok(())
 }
--- a/src/db/bind_fields.rs
+++ b/src/db/bind_fields.rs
@@ -0,0 +1,59 @@
+
+use sqlx::{prelude::*, query::Query, sqlite::SqliteArguments, Encode, Sqlite};
+
+type BindFn = Box<
+    dyn for<'q> FnOnce(
+            Query<'q, Sqlite, SqliteArguments<'q>>,
+        ) -> Query<'q, Sqlite, SqliteArguments<'q>>
+        + Send,
+>;
+
+fn make_bind_fn<T>(value: T) -> BindFn
+where
+    T: for<'q> Encode<'q, Sqlite> + Type<Sqlite> + Send + 'static,
+{
+    Box::new(move |query| query.bind(value))
+}
+
+#[derive(Default)]
+pub struct BindFields {
+    binds: Vec<(&'static str, BindFn)>,
+}
+
+
+impl BindFields {
+    #[must_use]
+    pub fn push<'a>(
+        mut self,
+        field: &'static str,
+        value: &'a (impl for<'q> Encode<'q, Sqlite> + Type<Sqlite> + Send + 'static + Clone),
+    ) -> Self {
+        self.binds.push((field, make_bind_fn(value.clone())));
+        self
+    }
+
+    #[must_use]
+    pub fn extend(mut self, other: Self) -> Self {
+        self.binds.extend(other.binds);
+        self
+    }
+
+    pub fn bind_to_query<'q>(
+        self,
+        query: Query<'q, Sqlite, SqliteArguments<'q>>,
+    ) -> Query<'q, Sqlite, SqliteArguments<'q>> {
+        let mut query = query;
+        for (_, bind_fn) in self.binds {
+            query = bind_fn(query);
+        }
+        query
+    }
+
+    pub fn bind_names(&self) -> impl Iterator<Item = &'static str> + '_ {
+        self.binds.iter().map(|(name, _)| *name)
+    }
+
+    pub fn bind_placeholders(&self) -> impl Iterator<Item = &'static str> + '_ {
+        std::iter::repeat_n("?", self.binds.len())
+    }
+}
--- a/src/db/dao/bid_dao.rs
+++ b/src/db/dao/bid_dao.rs
@@ -0,0 +1,272 @@
+use crate::db::{
+    bid::{NewBid, PersistedBid, PersistedBidFields},
+    bind_fields::BindFields,
+    DbListingId, DbUserId,
+};
+use anyhow::Result;
+use chrono::Utc;
+use itertools::Itertools as _;
+use sqlx::{prelude::*, sqlite::SqliteRow, SqlitePool};
+
+#[derive(Clone)]
+pub struct BidDAO(SqlitePool);
+
+impl BidDAO {
+    pub fn new(pool: SqlitePool) -> Self {
+        Self(pool)
+    }
+}
+
+#[allow(unused)]
+impl BidDAO {
+    pub async fn insert_bid(&self, bid: &NewBid) -> Result<PersistedBid> {
+        let mut tx = self.0.begin().await?;
+
+        // First, validate that the listing is active within the transaction
+        // Note: SQLite doesn't support FOR UPDATE, but transactions provide isolation
+        let is_active: bool = sqlx::query_scalar("SELECT is_active FROM listings WHERE id = ?")
+            .bind(bid.listing_id)
+            .fetch_optional(&mut *tx)
+            .await?
+            .ok_or_else(|| anyhow::anyhow!("Listing not found"))?;
+
+        if !is_active {
+            return Err(anyhow::anyhow!("Cannot place bid on inactive listing"));
+        }
+
+        let now = Utc::now();
+        let binds = BindFields::default()
+            .push("listing_id", &bid.listing_id)
+            .push("buyer_id", &bid.buyer_id)
+            .push("bid_amount", &bid.bid_amount)
+            .push("description", &bid.description)
+            .push("is_cancelled", &bid.is_cancelled)
+            .push("slot_number", &bid.slot_number)
+            .push("proxy_bid_id", &bid.proxy_bid_id)
+            .push("created_at", &now)
+            .push("updated_at", &now);
+
+        let insert_bid_query_str = format!(
+            r#"
+                INSERT INTO bids ({}) VALUES ({})
+                RETURNING *
+            "#,
+            binds.bind_names().join(", "),
+            binds.bind_placeholders().join(", ")
+        );
+        let insert_bid_query = binds.bind_to_query(sqlx::query(&insert_bid_query_str));
+
+        let row = insert_bid_query.fetch_one(&mut *tx).await?;
+        tx.commit().await?;
+        Ok(PersistedBid::from_row(&row)?)
+    }
+
+    pub async fn bidder_ids_for_listing(&self, listing_id: DbListingId) -> Result<Vec<DbUserId>> {
+        let rows =
+            sqlx::query_as::<_, (DbUserId,)>("SELECT buyer_id FROM bids WHERE listing_id = ?")
+                .bind(listing_id)
+                .fetch_all(&self.0)
+                .await?;
+        Ok(rows.into_iter().map(|(id,)| id).collect())
+    }
+
+    pub async fn bids_for_listing(&self, listing_id: DbListingId) -> Result<Vec<PersistedBid>> {
+        let rows = sqlx::query_as::<_, PersistedBid>(
+            "SELECT * FROM bids WHERE listing_id = ? ORDER BY bid_amount DESC",
+        )
+        .bind(listing_id)
+        .fetch_all(&self.0)
+        .await?;
+        Ok(rows)
+    }
+}
+
+impl FromRow<'_, SqliteRow> for PersistedBid {
+    fn from_row(row: &'_ SqliteRow) -> std::result::Result<Self, sqlx::Error> {
+        Ok(PersistedBid {
+            persisted: PersistedBidFields::from_row(row)?,
+            listing_id: row.get("listing_id"),
+            buyer_id: row.get("buyer_id"),
+            bid_amount: row.get("bid_amount"),
+            description: row.get("description"),
+            is_cancelled: row.get("is_cancelled"),
+            slot_number: row.get("slot_number"),
+            proxy_bid_id: row.get("proxy_bid_id"),
+        })
+    }
+}
+
+impl FromRow<'_, SqliteRow> for PersistedBidFields {
+    fn from_row(row: &'_ SqliteRow) -> std::result::Result<Self, sqlx::Error> {
+        Ok(PersistedBidFields {
+            id: row.get("id"),
+            created_at: row.get("created_at"),
+            updated_at: row.get("updated_at"),
+        })
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use std::str::FromStr;
+
+    use super::*;
+    use crate::db::{
+        dao::listing_dao::{ListingEventSender, ListingUpdatedEvent},
+        listing::{BasicAuctionFields, ListingFields},
+        models::{listing::NewListing, user::NewUser},
+        CurrencyType, ListingDAO, MoneyAmount, UserDAO,
+    };
+    use crate::test_utils::create_test_pool;
+    use chrono::Utc;
+    use teloxide::types::UserId;
+
+    async fn create_test_user_and_listing() -> (
+        UserDAO,
+        ListingDAO,
+        BidDAO,
+        crate::db::DbUserId,
+        crate::db::DbListingId,
+    ) {
+        let (tx, _) = tokio::sync::mpsc::channel::<ListingUpdatedEvent>(1);
+        let pool = create_test_pool().await;
+        let user_dao = UserDAO::new(pool.clone());
+        let listing_dao = ListingDAO::new(pool.clone(), ListingEventSender::new(tx));
+        let bid_dao = BidDAO::new(pool);
+
+        // Create a test user
+        let new_user = NewUser {
+            persisted: (),
+            telegram_id: UserId(12345).into(),
+            first_name: "Test User".to_string(),
+            last_name: None,
+            username: Some("testuser".to_string()),
+            is_banned: false,
+        };
+
+        let user = user_dao
+            .insert_user(&new_user)
+            .await
+            .expect("Failed to insert test user");
+
+        // Create a test listing
+        let new_listing = NewListing {
+            persisted: (),
+            base: crate::db::listing::ListingBase {
+                seller_id: user.persisted.id,
+                title: "Test Listing".to_string(),
+                description: Some("Test description".to_string()),
+                currency_type: CurrencyType::Usd,
+                starts_at: Utc::now(),
+                ends_at: Utc::now() + chrono::Duration::hours(24),
+                is_active: true,
+            },
+            fields: ListingFields::BasicAuction(BasicAuctionFields {
+                starting_bid: MoneyAmount::from_str("10.00").unwrap(),
+                buy_now_price: Some(MoneyAmount::from_str("100.00").unwrap()),
+                min_increment: MoneyAmount::from_str("1.00").unwrap(),
+                anti_snipe_minutes: Some(5),
+            }),
+        };
+
+        let listing = listing_dao
+            .insert_listing(&new_listing)
+            .await
+            .expect("Failed to insert test listing");
+
+        (
+            user_dao,
+            listing_dao,
+            bid_dao,
+            user.persisted.id,
+            listing.persisted.id,
+        )
+    }
+
+    #[tokio::test]
+    async fn test_insert_bid_on_active_listing() {
+        let (_user_dao, _listing_dao, bid_dao, user_id, listing_id) =
+            create_test_user_and_listing().await;
+
+        let new_bid = NewBid {
+            persisted: (),
+            listing_id,
+            buyer_id: user_id,
+            bid_amount: MoneyAmount::from_str("25.50").unwrap(),
+            description: Some("Test bid description".to_string()),
+            is_cancelled: false,
+            slot_number: Some(1),
+            proxy_bid_id: None,
+        };
+
+        // Insert bid on active listing should succeed
+        let inserted_bid = bid_dao
+            .insert_bid(&new_bid)
+            .await
+            .expect("Failed to insert bid on active listing");
+
+        // Verify the inserted bid has the correct values
+        assert_eq!(inserted_bid.listing_id, new_bid.listing_id);
+        assert_eq!(inserted_bid.buyer_id, new_bid.buyer_id);
+        assert_eq!(inserted_bid.bid_amount, new_bid.bid_amount);
+        assert_eq!(inserted_bid.description, new_bid.description);
+        assert_eq!(inserted_bid.is_cancelled, new_bid.is_cancelled);
+        assert_eq!(inserted_bid.slot_number, new_bid.slot_number);
+        assert_eq!(inserted_bid.proxy_bid_id, new_bid.proxy_bid_id);
+
+        // Verify persisted fields are populated
+        assert!(inserted_bid.persisted.id.get() > 0);
+        assert!(inserted_bid.persisted.created_at <= chrono::Utc::now());
+        assert!(inserted_bid.persisted.updated_at <= chrono::Utc::now());
+        assert_eq!(
+            inserted_bid.persisted.created_at,
+            inserted_bid.persisted.updated_at
+        );
+    }
+
+    #[tokio::test]
+    async fn test_insert_bid_on_inactive_listing_fails() {
+        let (_user_dao, listing_dao, bid_dao, user_id, listing_id) =
+            create_test_user_and_listing().await;
+
+        // Mark the listing as inactive
+
+        listing_dao
+            .set_listing_is_active(listing_id, false)
+            .await
+            .unwrap();
+
+        let new_bid = NewBid {
+            persisted: (),
+            listing_id,
+            buyer_id: user_id,
+            bid_amount: MoneyAmount::from_str("25.50").unwrap(),
+            description: Some("Test bid description".to_string()),
+            is_cancelled: false,
+            slot_number: Some(1),
+            proxy_bid_id: None,
+        };
+
+        // Verify the listing is actually inactive
+        let updated_listing = listing_dao.find_by_id(listing_id).await.unwrap().unwrap();
+        assert!(
+            !updated_listing.base.is_active,
+            "Listing should be inactive"
+        );
+
+        // Insert bid on inactive listing should fail
+        let result = bid_dao.insert_bid(&new_bid).await;
+        match result {
+            Ok(_) => panic!("Expected bid insertion to fail on inactive listing, but it succeeded"),
+            Err(e) => {
+                let error_msg = e.to_string();
+                assert!(
+                    error_msg.contains("inactive listing")
+                        || error_msg.contains("Cannot place bid"),
+                    "Expected error about inactive listing, got: {}",
+                    error_msg
+                );
+            }
+        }
+    }
+}
--- a/src/db/dao/listing_dao.rs
+++ b/src/db/dao/listing_dao.rs
@@ -3,178 +3,445 @@
 //! Provides encapsulated CRUD operations for Listing entities

 use anyhow::Result;
-use sqlx::{sqlite::SqliteRow, Row, SqlitePool};
+use chrono::Utc;
+use itertools::Itertools;
+use sqlx::{sqlite::SqliteRow, FromRow, Row, SqlitePool};
+use std::fmt::Debug;
+use tokio::sync::mpsc::{Receiver, Sender};

 use crate::db::{
-    new_listing::{NewListing, NewListingFields},
-    ListingBase, ListingFields,
+    bind_fields::BindFields,
+    listing::{
+        BasicAuctionFields, BlindAuctionFields, FixedPriceListingFields, Listing, ListingBase,
+        ListingFields, MultiSlotAuctionFields, NewListing, PersistedListing,
+        PersistedListingFields,
+    },
+    DbListingId, DbUserId, ListingType,
 };

-use super::super::{Listing, ListingId, ListingType, UserRowId};
+#[derive(Debug, Clone, Copy)]
+pub enum ListingUpdatedEvent {
+    Created(DbListingId),
+    Updated(DbListingId),
+    Deleted(DbListingId),
+}
+
+#[derive(Clone)]
+pub struct ListingEventSender(Sender<ListingUpdatedEvent>);
+impl ListingEventSender {
+    pub fn new(sender: Sender<ListingUpdatedEvent>) -> Self {
+        Self(sender)
+    }
+
+    pub fn channel() -> (ListingEventSender, Receiver<ListingUpdatedEvent>) {
+        let (sender, receiver) = tokio::sync::mpsc::channel::<ListingUpdatedEvent>(1);
+        (ListingEventSender::new(sender), receiver)
+    }
+
+    pub fn send(&self, event: ListingUpdatedEvent) {
+        if let Err(e) = self.0.try_send(event) {
+            log::error!("Error sending listing updated event: {e:?}");
+        }
+    }
+}

 /// Data Access Object for Listing operations
-pub struct ListingDAO;
+#[derive(Clone)]
+pub struct ListingDAO(SqlitePool, ListingEventSender);

 impl ListingDAO {
+    pub fn new(pool: SqlitePool, sender: ListingEventSender) -> Self {
+        Self(pool, sender)
+    }
+
+    fn send_event(&self, event: ListingUpdatedEvent) {
+        self.1.send(event);
+    }
+
    /// Insert a new listing into the database
-    pub async fn insert_listing(pool: &SqlitePool, new_listing: &NewListing) -> Result<Listing> {
-        let listing_type = new_listing.listing_type();
-        let base = &new_listing.base;
-        let fields = &new_listing.fields;
+    pub async fn insert_listing(&self, listing: &NewListing) -> Result<PersistedListing> {
+        let now = Utc::now();

-        let base_query = match listing_type {
-            ListingType::BasicAuction => sqlx::query(
-                r#"
-                INSERT INTO listings (
-                    seller_id, listing_type, title, description, starts_at, ends_at,
-                    starting_bid, buy_now_price, min_increment, anti_snipe_minutes
-                ) VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
-                RETURNING id, seller_id, listing_type, title, description, starts_at, ends_at, created_at, updated_at,
-                          starting_bid, buy_now_price, min_increment, anti_snipe_minutes
-                "#,
-            ),
-            ListingType::MultiSlotAuction => sqlx::query(
-                r#"
-                INSERT INTO listings (
-                    seller_id, listing_type, title, description, starts_at, ends_at,
-                    starting_bid, buy_now_price, min_increment, slots_available, anti_snipe_minutes
-                ) VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
-                RETURNING id, seller_id, listing_type, title, description, starts_at, ends_at, created_at, updated_at,
-                          starting_bid, buy_now_price, min_increment, slots_available, anti_snipe_minutes
-                "#,
-            ),
-            ListingType::FixedPriceListing => sqlx::query(
-                r#"
-                INSERT INTO listings (
-                    seller_id, listing_type, title, description, starts_at, ends_at,
-                    buy_now_price, slots_available
-                ) VALUES (?, ?, ?, ?, ?, ?, ?, ?)
-                RETURNING id, seller_id, listing_type, title, description, starts_at, ends_at, created_at, updated_at,
-                          buy_now_price, slots_available
-                "#,
-            ),
-            ListingType::BlindAuction => sqlx::query(
-                r#"
-                INSERT INTO listings (
-                    seller_id, listing_type, title, description, starts_at, ends_at,
-                    starting_bid
-                ) VALUES (?, ?, ?, ?, ?, ?, ?)
-                RETURNING id, seller_id, listing_type, title, description, starts_at, ends_at, created_at, updated_at,
-                          starting_bid
-                "#,
-            ),
-        };
+        let binds = binds_for_listing(listing)
+            .push("seller_id", &listing.base.seller_id)
+            .push("starts_at", &listing.base.starts_at)
+            .push("ends_at", &listing.base.ends_at)
+            .push("created_at", &now)
+            .push("updated_at", &now);

-        let row = base_query
-            .bind(base.seller_id)
-            .bind(listing_type)
-            .bind(&base.title)
-            .bind(&base.description)
-            .bind(base.starts_at)
-            .bind(base.ends_at);
+        let query_str = format!(
+            r#"
+            INSERT INTO listings ({}) VALUES ({})
+            RETURNING *
+        "#,
+            binds.bind_names().join(", "),
+            binds.bind_placeholders().join(", "),
+        );

-        let row = match &fields {
-            NewListingFields::BasicAuction {
-                starting_bid,
-                buy_now_price,
-                min_increment,
-                anti_snipe_minutes,
-            } => row
-                .bind(starting_bid)
-                .bind(buy_now_price)
-                .bind(min_increment)
-                .bind(anti_snipe_minutes),
-            NewListingFields::MultiSlotAuction {
-                starting_bid,
-                buy_now_price,
-                min_increment,
-                slots_available,
-                anti_snipe_minutes,
-            } => row
-                .bind(starting_bid)
-                .bind(buy_now_price)
-                .bind(min_increment)
-                .bind(slots_available)
-                .bind(anti_snipe_minutes),
-            NewListingFields::FixedPriceListing {
-                buy_now_price,
-                slots_available,
-            } => row.bind(buy_now_price).bind(slots_available),
-            NewListingFields::BlindAuction { starting_bid } => row.bind(starting_bid),
-        };
+        let row = binds
+            .bind_to_query(sqlx::query(&query_str))
+            .fetch_one(&self.0)
+            .await?;
+        let listing = PersistedListing::from_row(&row)?;
+        self.send_event(ListingUpdatedEvent::Created(listing.persisted.id));
+        Ok(listing)
+    }

-        let row = row.fetch_one(pool).await?;
-        Self::row_to_listing(row)
+    pub async fn update_listing(&self, listing: &PersistedListing) -> Result<PersistedListing> {
+        let now = Utc::now();
+        let binds = binds_for_listing(listing).push("updated_at", &now);
+
+        let query_str = format!(
+            r#"
+                UPDATE listings
+                SET {}
+                WHERE id = ?
+                AND   seller_id = ?
+                RETURNING *
+            "#,
+            binds
+                .bind_names()
+                .map(|name| format!("{name} = ?"))
+                .join(", "),
+        );
+
+        let row = binds
+            .bind_to_query(sqlx::query(&query_str))
+            .bind(listing.persisted.id)
+            .bind(listing.base.seller_id)
+            .fetch_one(&self.0)
+            .await?;
+        let listing = PersistedListing::from_row(&row)?;
+        self.send_event(ListingUpdatedEvent::Updated(listing.persisted.id));
+        Ok(listing)
    }

    /// Find a listing by its ID
-    pub async fn find_by_id(pool: &SqlitePool, listing_id: ListingId) -> Result<Option<Listing>> {
-        let result = sqlx::query("SELECT * FROM listings WHERE id = ?")
+    pub async fn find_by_id(&self, listing_id: DbListingId) -> Result<Option<PersistedListing>> {
+        let result = sqlx::query_as("SELECT * FROM listings WHERE id = ?")
            .bind(listing_id)
-            .fetch_optional(pool)
+            .fetch_optional(&self.0)
            .await?;

-        result.map(Self::row_to_listing).transpose()
+        Ok(result)
    }

    /// Find all listings by a seller
-    pub async fn find_by_seller(pool: &SqlitePool, seller_id: UserRowId) -> Result<Vec<Listing>> {
+    pub async fn find_by_seller(&self, seller_id: DbUserId) -> Result<Vec<PersistedListing>> {
        let rows =
-            sqlx::query("SELECT * FROM listings WHERE seller_id = ? ORDER BY created_at DESC")
+            sqlx::query_as("SELECT * FROM listings WHERE seller_id = ? ORDER BY created_at DESC")
                .bind(seller_id)
-                .fetch_all(pool)
+                .fetch_all(&self.0)
                .await?;
-
-        rows
-            .into_iter()
-            .map(Self::row_to_listing)
-            .collect::<Result<Vec<_>>>()
+        Ok(rows)
    }

    /// Delete a listing
-    pub async fn delete_listing(pool: &SqlitePool, listing_id: ListingId) -> Result<()> {
+    pub async fn delete_listing(&self, listing_id: DbListingId) -> Result<()> {
        sqlx::query("DELETE FROM listings WHERE id = ?")
            .bind(listing_id)
-            .execute(pool)
+            .execute(&self.0)
            .await?;

+        self.send_event(ListingUpdatedEvent::Deleted(listing_id));
+
        Ok(())
    }

-    fn row_to_listing(row: SqliteRow) -> Result<Listing> {
+    pub async fn set_listing_is_active(
+        &self,
+        listing_id: DbListingId,
+        is_active: bool,
+    ) -> Result<PersistedListing> {
+        let result = sqlx::query_as::<_, PersistedListing>(
+            r#"
+            UPDATE listings
+            SET is_active = ?
+            WHERE id = ?
+            RETURNING *"#,
+        )
+        .bind(is_active)
+        .bind(listing_id)
+        .fetch_one(&self.0)
+        .await?;
+        self.send_event(ListingUpdatedEvent::Updated(result.persisted.id));
+        Ok(result)
+    }
+
+    pub async fn find_next_ending_listing(&self) -> Result<Option<PersistedListing>> {
+        let result = sqlx::query_as(
+            r#"
+            SELECT * FROM listings
+            WHERE is_active = 1
+            ORDER BY ends_at ASC
+            LIMIT 1"#,
+        )
+        .fetch_optional(&self.0)
+        .await?;
+        Ok(result)
+    }
+}
+
+fn binds_for_listing<P: Debug + Clone>(listing: &Listing<P>) -> BindFields {
+    BindFields::default()
+        .extend(binds_for_base(&listing.base))
+        .extend(binds_for_fields(&listing.fields))
+}
+
+fn binds_for_base(base: &ListingBase) -> BindFields {
+    BindFields::default()
+        .push("title", &base.title)
+        .push("description", &base.description)
+        .push("currency_type", &base.currency_type)
+        .push("starts_at", &base.starts_at)
+        .push("ends_at", &base.ends_at)
+        .push("is_active", &base.is_active)
+}
+
+fn binds_for_fields(fields: &ListingFields) -> BindFields {
+    match fields {
+        ListingFields::BasicAuction(fields) => BindFields::default()
+            .push("listing_type", &ListingType::BasicAuction)
+            .push("starting_bid", &fields.starting_bid)
+            .push("buy_now_price", &fields.buy_now_price)
+            .push("min_increment", &fields.min_increment)
+            .push("anti_snipe_minutes", &fields.anti_snipe_minutes),
+        ListingFields::MultiSlotAuction(fields) => BindFields::default()
+            .push("listing_type", &ListingType::MultiSlotAuction)
+            .push("starting_bid", &fields.starting_bid)
+            .push("buy_now_price", &fields.buy_now_price)
+            .push("min_increment", &fields.min_increment)
+            .push("slots_available", &fields.slots_available)
+            .push("anti_snipe_minutes", &fields.anti_snipe_minutes),
+        ListingFields::FixedPriceListing(fields) => BindFields::default()
+            .push("listing_type", &ListingType::FixedPriceListing)
+            .push("buy_now_price", &fields.buy_now_price)
+            .push("slots_available", &fields.slots_available),
+        ListingFields::BlindAuction(fields) => BindFields::default()
+            .push("listing_type", &ListingType::BlindAuction)
+            .push("starting_bid", &fields.starting_bid),
+    }
+}
+
+impl FromRow<'_, SqliteRow> for PersistedListing {
+    fn from_row(row: &'_ SqliteRow) -> std::result::Result<Self, sqlx::Error> {
        let listing_type = row.get("listing_type");
-        let base = ListingBase {
-            id: ListingId::new(row.get("id")),
-            seller_id: row.get("seller_id"),
-            title: row.get("title"),
-            description: row.get("description"),
-            starts_at: row.get("starts_at"),
-            ends_at: row.get("ends_at"),
+        let persisted = PersistedListingFields {
+            id: row.get("id"),
            created_at: row.get("created_at"),
            updated_at: row.get("updated_at"),
        };
-        let fields = match listing_type {
-            ListingType::BasicAuction => ListingFields::BasicAuction {
-                starting_bid: row.get("starting_bid"),
-                buy_now_price: row.get("buy_now_price"),
-                min_increment: row.get("min_increment"),
-                anti_snipe_minutes: row.get("anti_snipe_minutes"),
-            },
-            ListingType::MultiSlotAuction => ListingFields::MultiSlotAuction {
-                starting_bid: row.get("starting_bid"),
-                buy_now_price: row.get("buy_now_price"),
-                min_increment: row.get("min_increment"),
-                slots_available: row.get("slots_available"),
-                anti_snipe_minutes: row.get("anti_snipe_minutes"),
-            },
-            ListingType::FixedPriceListing => ListingFields::FixedPriceListing {
-                buy_now_price: row.get("buy_now_price"),
-                slots_available: row.get("slots_available"),
-            },
-            ListingType::BlindAuction => ListingFields::BlindAuction {
-                starting_bid: row.get("starting_bid"),
-            },
+        let base = ListingBase {
+            seller_id: row.get("seller_id"),
+            title: row.get("title"),
+            description: row.get("description"),
+            currency_type: row.get("currency_type"),
+            starts_at: row.get("starts_at"),
+            ends_at: row.get("ends_at"),
+            is_active: row.get("is_active"),
        };
-        Ok(Listing { base, fields })
+        let fields = match listing_type {
+            ListingType::BasicAuction => ListingFields::BasicAuction(BasicAuctionFields {
+                starting_bid: row.get("starting_bid"),
+                buy_now_price: row.get("buy_now_price"),
+                min_increment: row.get("min_increment"),
+                anti_snipe_minutes: row.get("anti_snipe_minutes"),
+            }),
+            ListingType::MultiSlotAuction => {
+                ListingFields::MultiSlotAuction(MultiSlotAuctionFields {
+                    starting_bid: row.get("starting_bid"),
+                    buy_now_price: row.get("buy_now_price"),
+                    min_increment: row.get("min_increment"),
+                    slots_available: row.get("slots_available"),
+                    anti_snipe_minutes: row.get("anti_snipe_minutes"),
+                })
+            }
+            ListingType::FixedPriceListing => {
+                ListingFields::FixedPriceListing(FixedPriceListingFields {
+                    buy_now_price: row.get("buy_now_price"),
+                    slots_available: row.get("slots_available"),
+                })
+            }
+            ListingType::BlindAuction => ListingFields::BlindAuction(BlindAuctionFields {
+                starting_bid: row.get("starting_bid"),
+            }),
+        };
+        Ok(PersistedListing {
+            persisted,
+            base,
+            fields,
+        })
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use crate::test_utils::{create_deps, with_test_listing, with_test_user};
+    use chrono::{Duration, Utc};
+    use rstest::rstest;
+
+    #[tokio::test]
+    async fn test_find_next_ending_listing_no_active_listings() {
+        let deps = create_deps().await;
+        let listing_dao = &deps.deps.get::<crate::db::DAOs>().listing;
+
+        let result = listing_dao
+            .find_next_ending_listing()
+            .await
+            .expect("Failed to query for next ending listing");
+
+        assert!(
+            result.is_none(),
+            "Expected no listings when database is empty"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_find_next_ending_listing_single_active_listing() {
+        let deps = create_deps().await;
+        let listing_dao = &deps.deps.get::<crate::db::DAOs>().listing;
+
+        let seller = with_test_user(&deps.deps, |_| {}).await;
+        let ends_at = Utc::now() + Duration::hours(1);
+
+        let inserted_listing = with_test_listing(&deps.deps, &seller, |listing| {
+            listing.base.ends_at = ends_at;
+        })
+        .await;
+
+        let result = listing_dao
+            .find_next_ending_listing()
+            .await
+            .expect("Failed to query for next ending listing");
+
+        assert!(result.is_some(), "Expected to find the active listing");
+        let found_listing = result.unwrap();
+        assert_eq!(found_listing.persisted.id, inserted_listing.persisted.id);
+        assert_eq!(found_listing.base.ends_at, ends_at);
+        assert!(found_listing.base.is_active);
+    }
+
+    #[rstest]
+    #[case(3, vec![2, 1, 3], 1)] // Multiple listings, should return the one ending soonest (index 1)
+    #[case(2, vec![1, 2], 0)] // Two listings, should return the one ending first (index 0)
+    #[case(4, vec![4, 1, 3, 2], 1)] // Four listings, should return the one ending soonest (index 1)
+    #[tokio::test]
+    async fn test_find_next_ending_listing_multiple_active_listings(
+        #[case] _num_listings: usize,
+        #[case] hours_from_now: Vec<i64>,
+        #[case] expected_index: usize,
+    ) {
+        let deps = create_deps().await;
+        let listing_dao = &deps.deps.get::<crate::db::DAOs>().listing;
+        let seller = with_test_user(&deps.deps, |_| {}).await;
+
+        let mut inserted_listings = Vec::new();
+        let base_time = Utc::now();
+
+        // Create multiple listings with different end times
+        for (_i, hours) in hours_from_now.iter().enumerate() {
+            let ends_at = base_time + Duration::hours(*hours);
+            let inserted_listing = with_test_listing(&deps.deps, &seller, |listing| {
+                listing.base.ends_at = ends_at;
+            })
+            .await;
+            inserted_listings.push(inserted_listing);
+        }
+
+        let result = listing_dao
+            .find_next_ending_listing()
+            .await
+            .expect("Failed to query for next ending listing");
+
+        assert!(result.is_some(), "Expected to find an active listing");
+        let found_listing = result.unwrap();
+
+        // Should return the listing that ends soonest
+        let expected_listing = &inserted_listings[expected_index];
+        assert_eq!(found_listing.persisted.id, expected_listing.persisted.id);
+        assert_eq!(found_listing.base.ends_at, expected_listing.base.ends_at);
+    }
+
+    #[tokio::test]
+    async fn test_find_next_ending_listing_ignores_inactive_listings() {
+        let deps = create_deps().await;
+        let listing_dao = &deps.deps.get::<crate::db::DAOs>().listing;
+        let seller = with_test_user(&deps.deps, |_| {}).await;
+
+        // Create an inactive listing that ends sooner
+        let inactive_ends_at = Utc::now() + Duration::hours(1);
+        with_test_listing(&deps.deps, &seller, |listing| {
+            listing.base.ends_at = inactive_ends_at;
+            listing.base.is_active = false;
+        })
+        .await;
+
+        // Create an active listing that ends later
+        let active_ends_at = Utc::now() + Duration::hours(2);
+        let inserted_active_listing = with_test_listing(&deps.deps, &seller, |listing| {
+            listing.base.ends_at = active_ends_at;
+        })
+        .await;
+
+        let result = listing_dao
+            .find_next_ending_listing()
+            .await
+            .expect("Failed to query for next ending listing");
+
+        assert!(result.is_some(), "Expected to find the active listing");
+        let found_listing = result.unwrap();
+
+        // Should return the active listing, not the inactive one that ends sooner
+        assert_eq!(
+            found_listing.persisted.id,
+            inserted_active_listing.persisted.id
+        );
+        assert_eq!(found_listing.base.ends_at, active_ends_at);
+        assert!(found_listing.base.is_active);
+    }
+
+    #[tokio::test]
+    async fn test_find_next_ending_listing_with_mixed_active_inactive() {
+        let deps = create_deps().await;
+        let listing_dao = &deps.deps.get::<crate::db::DAOs>().listing;
+        let seller = with_test_user(&deps.deps, |_| {}).await;
+
+        let base_time = Utc::now();
+        let mut inserted_active_listings = Vec::new();
+
+        // Create a mix of active and inactive listings
+        let listing_configs = vec![
+            (1, false), // inactive, ends in 1 hour
+            (2, true),  // active, ends in 2 hours
+            (3, false), // inactive, ends in 3 hours
+            (4, true),  // active, ends in 4 hours
+            (5, true),  // active, ends in 5 hours
+        ];
+
+        for (hours, is_active) in listing_configs {
+            let ends_at = base_time + Duration::hours(hours);
+            let inserted_listing = with_test_listing(&deps.deps, &seller, |listing| {
+                listing.base.ends_at = ends_at;
+                listing.base.is_active = is_active;
+            })
+            .await;
+
+            if is_active {
+                inserted_active_listings.push(inserted_listing);
+            }
+        }
+
+        let result = listing_dao
+            .find_next_ending_listing()
+            .await
+            .expect("Failed to query for next ending listing");
+
+        assert!(result.is_some(), "Expected to find an active listing");
+        let found_listing = result.unwrap();
+
+        // Should return the first active listing (ends in 2 hours), ignoring inactive ones
+        let expected_listing = &inserted_active_listings[0]; // The one ending in 2 hours
+        assert_eq!(found_listing.persisted.id, expected_listing.persisted.id);
+        assert!(found_listing.base.is_active);
    }
 }
--- a/src/db/dao/mod.rs
+++ b/src/db/dao/mod.rs
@@ -1,6 +1,27 @@
-pub mod listing_dao;
-pub mod user_dao;
+mod bid_dao;
+mod listing_dao;
+mod user_dao;

 // Re-export DAO structs for easy access
+pub use bid_dao::BidDAO;
 pub use listing_dao::ListingDAO;
+pub use listing_dao::{ListingEventSender, ListingUpdatedEvent};
+use sqlx::SqlitePool;
 pub use user_dao::UserDAO;
+
+#[derive(Clone)]
+pub struct DAOs {
+    pub user: UserDAO,
+    pub listing: ListingDAO,
+    pub bid: BidDAO,
+}
+
+impl DAOs {
+    pub fn new(pool: SqlitePool, sender: ListingEventSender) -> Self {
+        Self {
+            user: UserDAO::new(pool.clone()),
+            listing: ListingDAO::new(pool.clone(), sender),
+            bid: BidDAO::new(pool),
+        }
+    }
+}
--- a/src/db/dao/user_dao.rs
+++ b/src/db/dao/user_dao.rs
@@ -3,129 +3,193 @@
 //! Provides encapsulated CRUD operations for User entities

 use anyhow::Result;
-use sqlx::SqlitePool;
+use itertools::Itertools as _;
+use sqlx::{sqlite::SqliteRow, FromRow, SqlitePool};

 use crate::db::{
-    models::user::{NewUser, User},
-    TelegramUserId, UserRowId,
+    bind_fields::BindFields,
+    models::user::NewUser,
+    user::{PersistedUser, PersistedUserFields},
+    DbTelegramUserId, DbUserId,
 };

 /// Data Access Object for User operations
-pub struct UserDAO;
+#[derive(Clone)]
+pub struct UserDAO(SqlitePool);

 #[allow(unused)]
 impl UserDAO {
-    /// Insert a new user into the database
-    pub async fn insert_user(pool: &SqlitePool, new_user: &NewUser) -> Result<User> {
-        let user = sqlx::query_as::<_, User>(
-            r#"
-            INSERT INTO users (telegram_id, username, display_name)
-            VALUES (?, ?, ?)
-            RETURNING id, telegram_id, username, display_name, is_banned, created_at, updated_at
-            "#,
-        )
-        .bind(new_user.telegram_id)
-        .bind(&new_user.username)
-        .bind(&new_user.display_name)
-        .fetch_one(pool)
-        .await?;
+    pub fn new(pool: SqlitePool) -> Self {
+        Self(pool)
+    }

-        Ok(user)
+    /// Insert a new user into the database
+    pub async fn insert_user(&self, new_user: &NewUser) -> Result<PersistedUser> {
+        let binds = BindFields::default()
+            .push("telegram_id", &new_user.telegram_id)
+            .push("first_name", &new_user.first_name)
+            .push("last_name", &new_user.last_name)
+            .push("username", &new_user.username);
+
+        let query_str = format!(
+            r#"
+                INSERT INTO users ({})
+                VALUES ({})
+                RETURNING *
+            "#,
+            binds.bind_names().join(", "),
+            binds.bind_placeholders().join(", "),
+        );
+        let query = sqlx::query(&query_str);
+        let row = binds.bind_to_query(query).fetch_one(&self.0).await?;
+
+        Ok(FromRow::from_row(&row)?)
    }

    /// Find a user by their ID
-    pub async fn find_by_id(pool: &SqlitePool, user_id: UserRowId) -> Result<Option<User>> {
-        let user = sqlx::query_as::<_, User>(
-            "SELECT id, telegram_id, username, display_name, is_banned, created_at, updated_at FROM users WHERE id = ?"
+    pub async fn find_by_id(&self, user_id: DbUserId) -> Result<Option<PersistedUser>> {
+        Ok(
+            sqlx::query_as::<_, PersistedUser>("SELECT * FROM users WHERE id = ? ")
+                .bind(user_id)
+                .fetch_optional(&self.0)
+                .await?,
        )
-        .bind(user_id)
-        .fetch_optional(pool)
-        .await?;
-
-        Ok(user)
    }

    /// Find a user by their Telegram ID
    pub async fn find_by_telegram_id(
-        pool: &SqlitePool,
-        telegram_id: impl Into<TelegramUserId>,
-    ) -> Result<Option<User>> {
+        &self,
+        telegram_id: impl Into<DbTelegramUserId>,
+    ) -> Result<Option<PersistedUser>> {
        let telegram_id = telegram_id.into();
-        let user = sqlx::query_as::<_, User>(
-            "SELECT id, telegram_id, username, display_name, is_banned, created_at, updated_at FROM users WHERE telegram_id = ?"
+        Ok(sqlx::query_as(
+            r#"
+                SELECT id, telegram_id, username, first_name, last_name, is_banned, created_at, updated_at
+                FROM users
+                WHERE telegram_id = ?
+            "#,
        )
        .bind(telegram_id)
-        .fetch_optional(pool)
-        .await?;
+        .fetch_optional(&self.0)
+        .await?)
+    }

+    pub async fn find_or_create_by_telegram_user(
+        &self,
+        user: teloxide::types::User,
+    ) -> Result<PersistedUser> {
+        let binds = BindFields::default()
+            .push("telegram_id", &DbTelegramUserId::from(user.id))
+            .push("username", &user.username)
+            .push("first_name", &user.first_name)
+            .push("last_name", &user.last_name);
+
+        let query_str = format!(
+            r#"
+                INSERT INTO users ({})
+                VALUES ({})
+                ON CONFLICT (telegram_id) DO UPDATE SET
+                    username = EXCLUDED.username,
+                    first_name = EXCLUDED.first_name,
+                    last_name = EXCLUDED.last_name
+                RETURNING *
+            "#,
+            binds.bind_names().join(", "),
+            binds.bind_placeholders().join(", "),
+        );
+
+        let row = binds
+            .bind_to_query(sqlx::query(&query_str))
+            .fetch_one(&self.0)
+            .await?;
+
+        let user = FromRow::from_row(&row)?;
+        log::info!("load user from db: {user:?}");
        Ok(user)
    }

    /// Update a user's information
-    pub async fn update_user(pool: &SqlitePool, user: &User) -> Result<User> {
-        let updated_user = sqlx::query_as::<_, User>(
+    pub async fn update_user(&self, user: &PersistedUser) -> Result<PersistedUser> {
+        let updated_user = sqlx::query_as::<_, PersistedUser>(
            r#"
            UPDATE users
-            SET username = ?, display_name = ?, is_banned = ?, updated_at = CURRENT_TIMESTAMP
+            SET username = ?, first_name = ?, last_name = ?, is_banned = ?, updated_at = CURRENT_TIMESTAMP
            WHERE id = ?
-            RETURNING id, telegram_id, username, display_name, is_banned, created_at, updated_at
+            RETURNING id, telegram_id, first_name, last_name, username, is_banned, created_at, updated_at
            "#,
        )
        .bind(&user.username)
-        .bind(&user.display_name)
+        .bind(&user.first_name)
+        .bind(&user.last_name)
        .bind(user.is_banned) // sqlx automatically converts bool to INTEGER for SQLite
-        .bind(user.id)
-        .fetch_one(pool)
+        .bind(user.persisted.id)
+        .fetch_one(&self.0)
        .await?;

        Ok(updated_user)
    }

    /// Set a user's ban status
-    pub async fn set_ban_status(
-        pool: &SqlitePool,
-        user_id: UserRowId,
-        is_banned: bool,
-    ) -> Result<()> {
+    pub async fn set_ban_status(&self, user_id: DbUserId, is_banned: bool) -> Result<()> {
        sqlx::query("UPDATE users SET is_banned = ?, updated_at = CURRENT_TIMESTAMP WHERE id = ?")
            .bind(is_banned) // sqlx automatically converts bool to INTEGER for SQLite
            .bind(user_id)
-            .execute(pool)
+            .execute(&self.0)
            .await?;

        Ok(())
    }

    /// Delete a user (soft delete by setting is_banned = true might be better in production)
-    pub async fn delete_user(pool: &SqlitePool, user_id: UserRowId) -> Result<()> {
+    pub async fn delete_user(&self, user_id: DbUserId) -> Result<()> {
        sqlx::query("DELETE FROM users WHERE id = ?")
            .bind(user_id)
-            .execute(pool)
+            .execute(&self.0)
            .await?;

        Ok(())
    }

-    /// Get or create a user (find by telegram_id, create if not found)
-    pub async fn get_or_create_user(
-        pool: &SqlitePool,
-        telegram_id: TelegramUserId,
-        username: Option<String>,
-        display_name: Option<String>,
-    ) -> Result<User> {
-        // Try to find existing user first
-        if let Some(existing_user) = Self::find_by_telegram_id(pool, telegram_id).await? {
-            return Ok(existing_user);
+    pub async fn where_in_ids(
+        &self,
+        ids: impl Iterator<Item = DbUserId>,
+    ) -> Result<Vec<PersistedUser>> {
+        let mut builder =
+            sqlx::query_builder::QueryBuilder::new("SELECT * FROM users WHERE id IN (");
+        let mut count = 0;
+        for id in ids {
+            count += 1;
+            builder.push_bind(id);
        }
+        if count == 0 {
+            return Ok(vec![]);
+        }
+        builder.push(")");

-        // Create new user if not found
-        let new_user = NewUser {
-            telegram_id,
-            username,
-            display_name,
-        };
+        let rows = builder.build().fetch_all(&self.0).await?;
+        Ok(rows
+            .into_iter()
+            .map(|row| PersistedUser::from_row(&row))
+            .collect::<Result<Vec<_>, _>>()?)
+    }
+}

-        Self::insert_user(pool, &new_user).await
+impl FromRow<'_, SqliteRow> for PersistedUser {
+    fn from_row(row: &'_ SqliteRow) -> std::result::Result<Self, sqlx::Error> {
+        use sqlx::Row as _;
+
+        Ok(PersistedUser {
+            persisted: PersistedUserFields {
+                id: row.get("id"),
+                created_at: row.get("created_at"),
+                updated_at: row.get("updated_at"),
+            },
+            telegram_id: row.get("telegram_id"),
+            username: row.get("username"),
+            first_name: row.get("first_name"),
+            last_name: row.get("last_name"),
+            is_banned: row.get("is_banned"),
+        })
    }
 }

@@ -133,12 +197,11 @@ impl UserDAO {
 mod tests {
    use super::*;
    use crate::db::models::user::NewUser;
-    use rstest::rstest;
    use sqlx::SqlitePool;
    use teloxide::types::UserId;

    /// Create test database for UserDAO tests
-    async fn create_test_pool() -> SqlitePool {
+    async fn create_test_dao() -> UserDAO {
        let pool = SqlitePool::connect("sqlite::memory:")
            .await
            .expect("Failed to create in-memory database");
@@ -149,118 +212,106 @@ mod tests {
            .await
            .expect("Failed to run database migrations");

-        pool
+        UserDAO::new(pool)
    }

    #[tokio::test]
    async fn test_insert_and_find_user() {
-        let pool = create_test_pool().await;
+        let dao = create_test_dao().await;

        let new_user = NewUser {
+            persisted: (),
            telegram_id: 12345.into(),
+            first_name: "Test User".to_string(),
+            last_name: None,
            username: Some("testuser".to_string()),
-            display_name: Some("Test User".to_string()),
+            is_banned: false,
        };

        // Insert user
-        let inserted_user = UserDAO::insert_user(&pool, &new_user)
+        let inserted_user = dao
+            .insert_user(&new_user)
            .await
            .expect("Failed to insert user");

        assert_eq!(inserted_user.telegram_id, 12345.into());
        assert_eq!(inserted_user.username, Some("testuser".to_string()));
-        assert_eq!(inserted_user.display_name, Some("Test User".to_string()));
-        assert_eq!(inserted_user.is_banned, false);
+        assert_eq!(inserted_user.first_name, "Test User".to_string());
+        assert!(!inserted_user.is_banned);

        // Find by ID
-        let found_user = UserDAO::find_by_id(&pool, inserted_user.id)
+        let found_user = dao
+            .find_by_id(inserted_user.persisted.id)
            .await
            .expect("Failed to find user by id")
            .expect("User should be found");

-        assert_eq!(found_user.id, inserted_user.id);
+        assert_eq!(found_user.persisted.id, inserted_user.persisted.id);
        assert_eq!(found_user.telegram_id, inserted_user.telegram_id);

        // Find by telegram ID
-        let found_by_telegram = UserDAO::find_by_telegram_id(&pool, UserId(12345))
+        let found_by_telegram = dao
+            .find_by_telegram_id(UserId(12345))
            .await
            .expect("Failed to find user by telegram_id")
            .expect("User should be found");

-        assert_eq!(found_by_telegram.id, inserted_user.id);
+        assert_eq!(found_by_telegram.persisted.id, inserted_user.persisted.id);
        assert_eq!(found_by_telegram.telegram_id, 12345.into());
    }

    #[tokio::test]
    async fn test_get_or_create_user() {
-        let pool = create_test_pool().await;
+        let dao = create_test_dao().await;

        // First call should create the user
-        let user1 = UserDAO::get_or_create_user(
-            &pool,
-            67890.into(),
-            Some("newuser".to_string()),
-            Some("New User".to_string()),
-        )
-        .await
-        .expect("Failed to get or create user");
+        let user1 = dao
+            .find_or_create_by_telegram_user(teloxide::types::User {
+                id: UserId(67890),
+                is_bot: false,
+                first_name: "New User".to_string(),
+                last_name: None,
+                username: Some("newuser".to_string()),
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            })
+            .await
+            .expect("Failed to get or create user");

        assert_eq!(user1.telegram_id, 67890.into());
        assert_eq!(user1.username, Some("newuser".to_string()));

        // Second call should return the same user
-        let user2 = UserDAO::get_or_create_user(
-            &pool,
-            67890.into(),
-            Some("differentusername".to_string()), // This should be ignored
-            Some("Different Name".to_string()),    // This should be ignored
-        )
-        .await
-        .expect("Failed to get or create user");
+        let user2 = dao
+            .find_or_create_by_telegram_user(teloxide::types::User {
+                id: UserId(67890),
+                is_bot: false,
+                first_name: "New User".to_string(),
+                last_name: None,
+                username: Some("newuser".to_string()),
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            })
+            .await
+            .expect("Failed to get or create user");

-        assert_eq!(user1.id, user2.id);
+        assert_eq!(user1.persisted.id, user2.persisted.id);
        assert_eq!(user2.username, Some("newuser".to_string())); // Original username preserved
    }

-    #[rstest]
-    #[case(true)]
-    #[case(false)]
-    #[tokio::test]
-    async fn test_ban_status_operations(#[case] is_banned: bool) {
-        let pool = create_test_pool().await;
-
-        let new_user = NewUser {
-            telegram_id: 99999.into(),
-            username: Some("bantest".to_string()),
-            display_name: Some("Ban Test User".to_string()),
-        };
-
-        let user = UserDAO::insert_user(&pool, &new_user)
-            .await
-            .expect("Failed to insert user");
-
-        // Set ban status
-        UserDAO::set_ban_status(&pool, user.id, is_banned)
-            .await
-            .expect("Failed to set ban status");
-
-        // Verify ban status
-        let updated_user = UserDAO::find_by_id(&pool, user.id)
-            .await
-            .expect("Failed to find user")
-            .expect("User should exist");
-
-        assert_eq!(updated_user.is_banned, is_banned);
-    }
-
    #[tokio::test]
    async fn test_update_user() {
-        let pool = create_test_pool().await;
+        let pool = create_test_dao().await;

        let new_user = NewUser {
+            persisted: (),
            telegram_id: 55555.into(),
            username: Some("oldname".to_string()),
-            display_name: Some("Old Name".to_string()),
+            first_name: "Old Name".to_string(),
+            last_name: None,
+            is_banned: false,
        };

        let mut user = UserDAO::insert_user(&pool, &new_user)
@@ -269,7 +320,7 @@ mod tests {

        // Update user information
        user.username = Some("newname".to_string());
-        user.display_name = Some("New Name".to_string());
+        user.first_name = "New Name".to_string();
        user.is_banned = true;

        let updated_user = UserDAO::update_user(&pool, &user)
@@ -277,18 +328,21 @@ mod tests {
            .expect("Failed to update user");

        assert_eq!(updated_user.username, Some("newname".to_string()));
-        assert_eq!(updated_user.display_name, Some("New Name".to_string()));
-        assert_eq!(updated_user.is_banned, true);
+        assert_eq!(updated_user.first_name, "New Name".to_string());
+        assert!(updated_user.is_banned);
    }

    #[tokio::test]
    async fn test_delete_user() {
-        let pool = create_test_pool().await;
+        let pool = create_test_dao().await;

        let new_user = NewUser {
+            persisted: (),
            telegram_id: 77777.into(),
            username: Some("deleteme".to_string()),
-            display_name: Some("Delete Me".to_string()),
+            first_name: "Delete Me".to_string(),
+            last_name: None,
+            is_banned: false,
        };

        let user = UserDAO::insert_user(&pool, &new_user)
@@ -296,12 +350,12 @@ mod tests {
            .expect("Failed to insert user");

        // Delete user
-        UserDAO::delete_user(&pool, user.id)
+        UserDAO::delete_user(&pool, user.persisted.id)
            .await
            .expect("Failed to delete user");

        // Verify user is gone
-        let not_found = UserDAO::find_by_id(&pool, user.id)
+        let not_found = UserDAO::find_by_id(&pool, user.persisted.id)
            .await
            .expect("Database operation should succeed");

@@ -310,10 +364,10 @@ mod tests {

    #[tokio::test]
    async fn test_find_nonexistent_user() {
-        let pool = create_test_pool().await;
+        let pool = create_test_dao().await;

        // Try to find a user that doesn't exist
-        let not_found = UserDAO::find_by_id(&pool, UserRowId::new(99999))
+        let not_found = UserDAO::find_by_id(&pool, DbUserId::new(99999))
            .await
            .expect("Database operation should succeed");

@@ -325,4 +379,145 @@ mod tests {

        assert!(not_found_by_telegram.is_none());
    }
+
+    mod upsert_tests {
+        use super::*;
+        use rstest::rstest;
+
+        #[rstest]
+        #[case(None, None, None)]
+        #[case(Some("new_user"), None, None)]
+        #[case(None, Some("New First"), None)]
+        #[case(None, None, Some("New Last"))]
+        #[case(Some(""), None, Some(""))]
+        #[tokio::test]
+        async fn test_upsert_updates_fields(
+            #[case] username: Option<&str>,
+            #[case] first_name: Option<&str>,
+            #[case] last_name: Option<&str>,
+        ) {
+            let pool = create_test_dao().await;
+            let user_id = UserId(12345);
+
+            let initial = teloxide::types::User {
+                id: user_id,
+                is_bot: false,
+                first_name: "First".into(),
+                last_name: Some("Last".into()),
+                username: Some("user".into()),
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            };
+
+            let created = UserDAO::find_or_create_by_telegram_user(&pool, initial)
+                .await
+                .unwrap();
+
+            let mut updated = teloxide::types::User {
+                id: user_id,
+                is_bot: false,
+                first_name: "First".into(),
+                last_name: Some("Last".into()),
+                username: Some("user".into()),
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            };
+            if let Some(u) = username {
+                updated.username = if u.is_empty() { None } else { Some(u.into()) };
+            }
+            if let Some(f) = first_name {
+                updated.first_name = f.into();
+            }
+            if let Some(l) = last_name {
+                updated.last_name = if l.is_empty() { None } else { Some(l.into()) };
+            }
+
+            let result = UserDAO::find_or_create_by_telegram_user(&pool, updated.clone())
+                .await
+                .unwrap();
+
+            assert_eq!(created.persisted.id, result.persisted.id);
+            assert_eq!(result.username, updated.username);
+            assert_eq!(result.first_name, updated.first_name);
+            assert_eq!(result.last_name, updated.last_name);
+        }
+
+        #[tokio::test]
+        async fn test_multiple_users_separate() {
+            let pool = create_test_dao().await;
+
+            let user1 = teloxide::types::User {
+                id: UserId(111),
+                is_bot: false,
+                first_name: "One".into(),
+                last_name: None,
+                username: Some("one".into()),
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            };
+            let user2 = teloxide::types::User {
+                id: UserId(222),
+                is_bot: false,
+                first_name: "Two".into(),
+                last_name: Some("Last".into()),
+                username: None,
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            };
+
+            let p1 = UserDAO::find_or_create_by_telegram_user(&pool, user1)
+                .await
+                .unwrap();
+            let p2 = UserDAO::find_or_create_by_telegram_user(&pool, user2)
+                .await
+                .unwrap();
+
+            assert_ne!(p1.persisted.id, p2.persisted.id);
+            assert_eq!(p1.telegram_id, UserId(111).into());
+            assert_eq!(p2.telegram_id, UserId(222).into());
+        }
+
+        #[tokio::test]
+        async fn test_upsert_preserves_id_and_timestamps() {
+            let pool = create_test_dao().await;
+
+            let user = teloxide::types::User {
+                id: UserId(333),
+                is_bot: false,
+                first_name: "Original".into(),
+                last_name: None,
+                username: Some("orig".into()),
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            };
+
+            let created = UserDAO::find_or_create_by_telegram_user(&pool, user)
+                .await
+                .unwrap();
+
+            let updated_user = teloxide::types::User {
+                id: UserId(333),
+                is_bot: false,
+                first_name: "Original".into(),
+                last_name: None,
+                username: Some("updated".into()),
+                language_code: None,
+                is_premium: false,
+                added_to_attachment_menu: false,
+            };
+
+            let updated = UserDAO::find_or_create_by_telegram_user(&pool, updated_user)
+                .await
+                .unwrap();
+
+            assert_eq!(created.persisted.id, updated.persisted.id);
+            assert_eq!(created.persisted.created_at, updated.persisted.created_at);
+            assert_eq!(updated.username, Some("updated".to_string()));
+        }
+    }
 }
--- a/src/db/mod.rs
+++ b/src/db/mod.rs
@@ -1,3 +1,4 @@
+pub mod bind_fields;
 pub mod dao;
 pub mod models;
 pub mod types;
--- a/src/db/models/bid.rs
+++ b/src/db/models/bid.rs
@@ -1,15 +1,26 @@
 use chrono::{DateTime, Utc};
-use sqlx::FromRow;

-use crate::db::MoneyAmount;
+use crate::db::{DbBidId, DbListingId, DbProxyBidId, DbUserId, MoneyAmount};
+
+pub type PersistedBid = Bid<PersistedBidFields>;
+#[allow(unused)]
+pub type NewBid = Bid<()>;
+
+#[derive(Debug, Clone, PartialEq)]
+#[allow(unused)]
+pub struct PersistedBidFields {
+    pub id: DbBidId,
+    pub created_at: DateTime<Utc>,
+    pub updated_at: DateTime<Utc>,
+}

 /// Actual bids placed on listings
+#[derive(Debug, Clone, PartialEq)]
 #[allow(unused)]
-#[derive(Debug, Clone, FromRow)]
-pub struct Bid {
-    pub id: i64,
-    pub listing_id: i64,
-    pub buyer_id: i64,
+pub struct Bid<P> {
+    pub persisted: P,
+    pub listing_id: DbListingId,
+    pub buyer_id: DbUserId,
    pub bid_amount: MoneyAmount,

    // For blind listings
@@ -20,20 +31,24 @@ pub struct Bid {
    pub slot_number: Option<i32>, // For multi-slot listings

    // Reference to proxy bid if auto-generated
-    pub proxy_bid_id: Option<i64>,
-
-    pub created_at: DateTime<Utc>,
-    pub updated_at: DateTime<Utc>,
+    pub proxy_bid_id: Option<DbProxyBidId>,
 }

-/// New bid data for insertion
-#[allow(unused)]
-#[derive(Debug, Clone)]
-pub struct NewBid {
-    pub listing_id: i64,
-    pub buyer_id: i64,
-    pub bid_amount: MoneyAmount,
-    pub description: Option<String>,
-    pub slot_number: Option<i32>,
-    pub proxy_bid_id: Option<i64>,
+impl<P> Bid<P> {
+    pub fn new_basic(
+        listing_id: DbListingId,
+        buyer_id: DbUserId,
+        bid_amount: MoneyAmount,
+    ) -> NewBid {
+        NewBid {
+            persisted: (),
+            listing_id,
+            buyer_id,
+            bid_amount,
+            description: None,
+            is_cancelled: false,
+            slot_number: None,
+            proxy_bid_id: None,
+        }
+    }
 }
--- a/src/db/models/listing.rs
+++ b/src/db/models/listing.rs
@@ -9,389 +9,213 @@
 //! The main `Listing` enum ensures that only valid fields are accessible for each type.
 //! Database mapping is handled through `ListingRow` with conversion traits.

-use super::listing_type::ListingType;
-use crate::db::{ListingId, MoneyAmount, UserRowId};
+use crate::db::{CurrencyType, DbListingId, DbUserId, ListingType, MoneyAmount};
 use chrono::{DateTime, Utc};
+use serde::{Deserialize, Serialize};
+use std::fmt::Debug;

-/// Main listing/auction entity
-#[derive(Debug, Clone)]
-#[allow(unused)]
-pub struct Listing {
-    pub base: ListingBase,
-    pub fields: ListingFields,
-}
+pub type NewListing = Listing<()>;
+pub type PersistedListing = Listing<PersistedListingFields>;

-/// Common fields shared by all listing types
-#[derive(Debug, Clone)]
-#[allow(unused)]
-pub struct ListingBase {
-    pub id: ListingId,
-    pub seller_id: UserRowId,
-    pub title: String,
-    pub description: Option<String>,
-    pub starts_at: DateTime<Utc>,
-    pub ends_at: DateTime<Utc>,
+#[derive(Debug, Clone, Serialize, Deserialize, Eq, PartialEq)]
+pub struct PersistedListingFields {
+    pub id: DbListingId,
    pub created_at: DateTime<Utc>,
    pub updated_at: DateTime<Utc>,
 }

-#[derive(Debug, Clone)]
-#[allow(unused)]
-pub enum ListingFields {
-    BasicAuction {
-        starting_bid: MoneyAmount,
-        buy_now_price: Option<MoneyAmount>,
-        min_increment: MoneyAmount,
-        anti_snipe_minutes: Option<i32>,
-    },
-    MultiSlotAuction {
-        starting_bid: MoneyAmount,
-        buy_now_price: MoneyAmount,
-        min_increment: Option<MoneyAmount>,
-        slots_available: i32,
-        anti_snipe_minutes: i32,
-    },
-    FixedPriceListing {
-        buy_now_price: MoneyAmount,
-        slots_available: i32,
-    },
-    BlindAuction {
-        starting_bid: MoneyAmount,
-    },
+/// Main listing/auction entity
+#[derive(Debug, Clone, Eq, PartialEq)]
+pub struct Listing<P: Debug + Clone> {
+    pub persisted: P,
+    pub base: ListingBase,
+    pub fields: ListingFields,
 }

-#[allow(unused)]
-impl Listing {
-    /// Get the listing type as an enum value
-    pub fn listing_type(&self) -> ListingType {
-        match &self.fields {
-            ListingFields::BasicAuction { .. } => ListingType::BasicAuction,
-            ListingFields::MultiSlotAuction { .. } => ListingType::MultiSlotAuction,
-            ListingFields::FixedPriceListing { .. } => ListingType::FixedPriceListing,
-            ListingFields::BlindAuction { .. } => ListingType::BlindAuction,
+pub type ListingBaseFields<'a> = (&'a ListingBase, &'a ListingFields);
+pub type ListingBaseFieldsMut<'a> = (&'a mut ListingBase, &'a mut ListingFields);
+
+impl<'a, P: Debug + Clone> From<&'a Listing<P>> for ListingBaseFields<'a> {
+    fn from(value: &'a Listing<P>) -> Self {
+        (&value.base, &value.fields)
+    }
+}
+impl<'a, P: Debug + Clone> From<&'a mut Listing<P>> for ListingBaseFieldsMut<'a> {
+    fn from(value: &'a mut Listing<P>) -> Self {
+        (&mut value.base, &mut value.fields)
+    }
+}
+
+/// Common fields shared by all listing types
+#[derive(Debug, Clone, Eq, PartialEq, Serialize, Deserialize)]
+pub struct ListingBase {
+    pub seller_id: DbUserId,
+    pub title: String,
+    pub description: Option<String>,
+    pub starts_at: DateTime<Utc>,
+    pub ends_at: DateTime<Utc>,
+    pub currency_type: CurrencyType,
+    pub is_active: bool,
+}
+
+impl ListingBase {
+    #[cfg(test)]
+    pub fn with_fields(self, fields: ListingFields) -> NewListing {
+        Listing {
+            persisted: (),
+            base: self,
+            fields,
        }
    }
 }

+/// Fields specific to basic auction listings
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub struct BasicAuctionFields {
+    pub starting_bid: MoneyAmount,
+    pub buy_now_price: Option<MoneyAmount>,
+    pub min_increment: MoneyAmount,
+    pub anti_snipe_minutes: Option<i32>,
+}
+
+/// Fields specific to multi-slot auction listings
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub struct MultiSlotAuctionFields {
+    pub starting_bid: MoneyAmount,
+    pub buy_now_price: MoneyAmount,
+    pub min_increment: Option<MoneyAmount>,
+    pub slots_available: i32,
+    pub anti_snipe_minutes: i32,
+}
+
+/// Fields specific to fixed price listings
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub struct FixedPriceListingFields {
+    pub buy_now_price: MoneyAmount,
+    pub slots_available: i32,
+}
+
+/// Fields specific to blind auction listings
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub struct BlindAuctionFields {
+    pub starting_bid: MoneyAmount,
+}
+
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub enum ListingFields {
+    BasicAuction(BasicAuctionFields),
+    MultiSlotAuction(MultiSlotAuctionFields),
+    FixedPriceListing(FixedPriceListingFields),
+    BlindAuction(BlindAuctionFields),
+}
+
+impl ListingFields {
+    pub fn listing_type(&self) -> ListingType {
+        match self {
+            ListingFields::BasicAuction(_) => ListingType::BasicAuction,
+            ListingFields::MultiSlotAuction(_) => ListingType::MultiSlotAuction,
+            ListingFields::FixedPriceListing(_) => ListingType::FixedPriceListing,
+            ListingFields::BlindAuction(_) => ListingType::BlindAuction,
+        }
+    }
+}
+
+impl From<&ListingFields> for ListingType {
+    fn from(fields: &ListingFields) -> ListingType {
+        fields.listing_type()
+    }
+}
+
 #[cfg(test)]
 mod tests {
-    use crate::db::{new_listing::NewListingBase, ListingDAO, TelegramUserId};
-    use crate::{assert_listing_timestamps_approx_eq, assert_timestamps_approx_eq_default};
+    use std::str::FromStr;

    use super::*;
-    use chrono::{Duration, Utc};
+    use crate::db::{DbTelegramUserId, UserDAO};
+    use chrono::Duration;
    use rstest::rstest;
-    use sqlx::SqlitePool;
-
-    /// Test utilities for creating an in-memory database with migrations
-    async fn create_test_pool() -> SqlitePool {
-        // Create an in-memory SQLite database for testing
-        let pool = SqlitePool::connect("sqlite::memory:")
-            .await
-            .expect("Failed to create in-memory database");
-
-        // Run the migration
-        apply_test_migrations(&pool).await;
-
-        pool
-    }
-
-    /// Apply the database migrations for testing
-    async fn apply_test_migrations(pool: &SqlitePool) {
-        // Run the actual migrations from the migrations directory
-        sqlx::migrate!("./migrations")
-            .run(pool)
-            .await
-            .expect("Failed to run database migrations");
-    }

    /// Create a test user using UserDAO and return their ID
    async fn create_test_user(
-        pool: &SqlitePool,
-        telegram_id: TelegramUserId,
+        user_dao: &UserDAO,
+        telegram_id: DbTelegramUserId,
        username: Option<&str>,
-    ) -> UserRowId {
-        use crate::db::{models::user::NewUser, UserDAO};
+    ) -> DbUserId {
+        use crate::db::models::user::NewUser;

        let new_user = NewUser {
+            persisted: (),
            telegram_id,
+            first_name: "Test User".to_string(),
+            last_name: None,
            username: username.map(|s| s.to_string()),
-            display_name: username.map(|s| s.to_string()),
+            is_banned: false,
        };

-        let user = UserDAO::insert_user(pool, &new_user)
+        let user = user_dao
+            .insert_user(&new_user)
            .await
            .expect("Failed to create test user");
-        user.id
-    }
-
-    /// Fetch a listing using ListingDAO by ID
-    async fn fetch_listing_using_dao(pool: &SqlitePool, id: ListingId) -> Listing {
-        use crate::db::ListingDAO;
-
-        ListingDAO::find_by_id(pool, id)
-            .await
-            .expect("Failed to fetch listing using DAO")
-            .expect("Listing should exist")
-    }
-
-    #[tokio::test]
-    async fn test_basic_auction_crud() {
-        let pool = create_test_pool().await;
-        let seller_id = create_test_user(&pool, 12345.into(), Some("testuser")).await;
-
-        // Create a basic auction listing
-        let starts_at = Utc::now();
-        let ends_at = starts_at + Duration::hours(24);
-
-        let new_listing = build_base_listing(
-            seller_id,
-            "Test Basic Auction",
-            Some("A test auction for basic functionality"),
-        )
-        .new_basic_auction(
-            MoneyAmount::from_str("10.00").unwrap(),
-            Some(MoneyAmount::from_str("100.00").unwrap()),
-            MoneyAmount::from_str("1.00").unwrap(),
-            Some(5),
-        );
-
-        // Insert using DAO
-        let actual_id = ListingDAO::insert_listing(&pool, &new_listing)
-            .await
-            .expect("Failed to insert listing")
-            .base
-            .id;
-
-        // Fetch back from database using DAO
-        let reconstructed_listing = fetch_listing_using_dao(&pool, actual_id).await;
-
-        // Verify the round trip worked correctly
-        match reconstructed_listing.fields {
-            ListingFields::BasicAuction {
-                starting_bid,
-                buy_now_price,
-                min_increment,
-                anti_snipe_minutes,
-            } => {
-                assert_eq!(reconstructed_listing.base.seller_id, seller_id);
-                assert_eq!(reconstructed_listing.base.title, "Test Basic Auction");
-                assert_eq!(
-                    reconstructed_listing.base.description,
-                    Some("A test auction for basic functionality".to_string())
-                );
-                assert_eq!(starting_bid, MoneyAmount::from_str("10.00").unwrap());
-                assert_eq!(
-                    buy_now_price,
-                    Some(MoneyAmount::from_str("100.00").unwrap())
-                );
-                assert_eq!(min_increment, MoneyAmount::from_str("1.00").unwrap());
-                assert_eq!(anti_snipe_minutes, Some(5));
-                assert_timestamps_approx_eq_default!(
-                    reconstructed_listing.base.starts_at,
-                    starts_at
-                );
-                assert_timestamps_approx_eq_default!(reconstructed_listing.base.ends_at, ends_at);
-            }
-            _ => panic!("Expected BasicAuction, got different variant"),
-        }
+        user.persisted.id
    }

    fn build_base_listing(
-        seller_id: UserRowId,
-        title: &str,
+        seller_id: DbUserId,
+        title: impl Into<String>,
        description: Option<&str>,
-    ) -> NewListingBase {
-        NewListingBase {
+        currency_type: CurrencyType,
+    ) -> ListingBase {
+        ListingBase {
            seller_id,
-            title: title.to_string(),
+            title: title.into(),
            description: description.map(|s| s.to_string()),
+            currency_type,
            starts_at: Utc::now(),
-            ends_at: Utc::now() + Duration::hours(24),
-        }
-    }
-
-    #[tokio::test]
-    async fn test_multi_slot_auction_crud() {
-        let pool = create_test_pool().await;
-        let seller_id = create_test_user(&pool, 67890.into(), Some("multislotuser")).await;
-        let listing = build_base_listing(seller_id, "Test Multi-Slot Auction", None)
-            .new_multi_slot_auction(
-                MoneyAmount::from_str("10.00").unwrap(),
-                MoneyAmount::from_str("50.00").unwrap(),
-                Some(MoneyAmount::from_str("2.50").unwrap()),
-                5,
-                10,
-            );
-
-        // Insert using DAO
-        let actual_id = ListingDAO::insert_listing(&pool, &listing)
-            .await
-            .expect("Failed to insert listing")
-            .base
-            .id;
-
-        // Fetch back from database using DAO
-        let reconstructed_listing = fetch_listing_using_dao(&pool, actual_id).await;
-
-        // Verify the round trip worked correctly
-        match reconstructed_listing.fields {
-            ListingFields::MultiSlotAuction {
-                starting_bid,
-                buy_now_price,
-                min_increment,
-                slots_available,
-                anti_snipe_minutes,
-            } => {
-                let reconstructed_base = reconstructed_listing.base;
-                assert_eq!(reconstructed_base.seller_id, seller_id);
-                assert_eq!(reconstructed_base.title, "Test Multi-Slot Auction");
-                assert_eq!(reconstructed_base.description, None);
-                assert_eq!(starting_bid, MoneyAmount::from_str("10.00").unwrap());
-                assert_eq!(buy_now_price, MoneyAmount::from_str("50.00").unwrap());
-                assert_eq!(min_increment, Some(MoneyAmount::from_str("2.50").unwrap()));
-                assert_eq!(slots_available, 5);
-                assert_eq!(anti_snipe_minutes, 10);
-                assert_listing_timestamps_approx_eq!(reconstructed_base, listing.base);
-            }
-            _ => panic!("Expected MultiSlotAuction, got different variant"),
-        }
-    }
-
-    #[tokio::test]
-    async fn test_fixed_price_listing_crud() {
-        let pool = create_test_pool().await;
-        let seller_id = create_test_user(&pool, 11111.into(), Some("fixedpriceuser")).await;
-
-        let listing = build_base_listing(
-            seller_id,
-            "Test Fixed Price Item",
-            Some("Fixed price sale with multiple slots"),
-        )
-        .new_fixed_price_listing(MoneyAmount::from_str("25.99").unwrap(), 3);
-
-        // Insert using DAO
-        let actual_id = ListingDAO::insert_listing(&pool, &listing)
-            .await
-            .expect("Failed to insert listing")
-            .base
-            .id;
-
-        // Fetch back from database using DAO
-        let reconstructed_listing = fetch_listing_using_dao(&pool, actual_id).await;
-
-        // Verify the round trip worked correctly
-        match reconstructed_listing.fields {
-            ListingFields::FixedPriceListing {
-                buy_now_price,
-                slots_available,
-            } => {
-                assert_eq!(reconstructed_listing.base.seller_id, seller_id);
-                assert_eq!(reconstructed_listing.base.title, "Test Fixed Price Item");
-                assert_eq!(
-                    listing.base.description,
-                    Some("Fixed price sale with multiple slots".to_string())
-                );
-                assert_eq!(buy_now_price, MoneyAmount::from_str("25.99").unwrap());
-                assert_eq!(slots_available, 3);
-                assert_listing_timestamps_approx_eq!(reconstructed_listing.base, listing.base);
-            }
-            _ => panic!("Expected FixedPriceListing, got different variant"),
-        }
-    }
-
-    #[tokio::test]
-    async fn test_blind_auction_crud() {
-        let pool = create_test_pool().await;
-        let seller_id = create_test_user(&pool, 99999.into(), Some("blinduser")).await;
-
-        let listing = build_base_listing(
-            seller_id,
-            "Test Blind Auction",
-            Some("Seller chooses winner"),
-        )
-        .new_blind_auction(MoneyAmount::from_str("100.00").unwrap());
-
-        // Insert using DAO
-        let actual_id = ListingDAO::insert_listing(&pool, &listing)
-            .await
-            .expect("Failed to insert listing")
-            .base
-            .id;
-
-        // Fetch back from database using DAO
-        let reconstructed_listing = fetch_listing_using_dao(&pool, actual_id).await;
-
-        // Verify the round trip worked correctly
-        match reconstructed_listing.fields {
-            ListingFields::BlindAuction { starting_bid } => {
-                assert_eq!(reconstructed_listing.base.seller_id, seller_id);
-                assert_eq!(reconstructed_listing.base.title, "Test Blind Auction");
-                assert_eq!(
-                    reconstructed_listing.base.description,
-                    Some("Seller chooses winner".to_string())
-                );
-                assert_listing_timestamps_approx_eq!(reconstructed_listing.base, listing.base);
-                assert_eq!(starting_bid, MoneyAmount::from_str("100.00").unwrap());
-            }
-            _ => panic!("Expected BlindAuction, got different variant"),
+            ends_at: Utc::now() + Duration::days(3),
+            is_active: true,
        }
    }

    #[rstest]
-    #[case("10.50", "100.00", "1.00")]
-    #[case("0.00", "50.00", "0.25")]
-    #[case("25.75", "999.99", "5.50")]
+    #[case(ListingFields::BlindAuction(BlindAuctionFields { starting_bid: MoneyAmount::from_str("100.00").unwrap() }))]
+    #[case(ListingFields::BasicAuction(BasicAuctionFields { starting_bid: MoneyAmount::from_str("100.00").unwrap(), buy_now_price: Some(MoneyAmount::from_str("100.00").unwrap()), min_increment: MoneyAmount::from_str("1.00").unwrap(), anti_snipe_minutes: Some(5) }))]
+    #[case(ListingFields::MultiSlotAuction(MultiSlotAuctionFields { starting_bid: MoneyAmount::from_str("100.00").unwrap(), buy_now_price: MoneyAmount::from_str("100.00").unwrap(), min_increment: Some(MoneyAmount::from_str("1.00").unwrap()), slots_available: 10, anti_snipe_minutes: 5 }))]
+    #[case(ListingFields::FixedPriceListing(FixedPriceListingFields { buy_now_price: MoneyAmount::from_str("100.00").unwrap(), slots_available: 10 }))]
    #[tokio::test]
-    async fn test_money_amount_precision_in_listings(
-        #[case] starting_bid_str: &str,
-        #[case] buy_now_price_str: &str,
-        #[case] min_increment_str: &str,
-    ) {
-        let pool = create_test_pool().await;
-        let seller_id = create_test_user(&pool, 55555.into(), Some("precisionuser")).await;
+    async fn test_blind_auction_crud(#[case] fields: ListingFields) {
+        use crate::{
+            db::{ListingDAO, ListingEventSender},
+            test_utils::create_test_pool,
+        };

-        let listing = build_base_listing(seller_id, "Precision Test Auction", None)
-            .new_basic_auction(
-                MoneyAmount::from_str(starting_bid_str).unwrap(),
-                Some(MoneyAmount::from_str(buy_now_price_str).unwrap()),
-                MoneyAmount::from_str(min_increment_str).unwrap(),
-                Some(5),
-            );
+        let (tx, _) = ListingEventSender::channel();
+        let pool = create_test_pool().await;
+        let user_dao = UserDAO::new(pool.clone());
+        let listing_dao = ListingDAO::new(pool.clone(), tx);
+        let seller_id = create_test_user(&user_dao, 99999.into(), Some("testuser")).await;
+        let new_listing = build_base_listing(
+            seller_id,
+            "Test Auction",
+            Some("Test description"),
+            CurrencyType::Usd,
+        )
+        .with_fields(fields);

        // Insert using DAO
-        let actual_id = ListingDAO::insert_listing(&pool, &listing)
+        let created_listing = listing_dao
+            .insert_listing(&new_listing)
            .await
-            .expect("Failed to insert listing")
-            .base
-            .id;
+            .expect("Failed to insert listing");

-        // Fetch back from database using DAO
-        let reconstructed_listing = fetch_listing_using_dao(&pool, actual_id).await;
+        assert_eq!(created_listing.base, new_listing.base);
+        assert_eq!(created_listing.fields, new_listing.fields);

-        // Verify precision is maintained
-        match reconstructed_listing.fields {
-            ListingFields::BasicAuction {
-                starting_bid,
-                buy_now_price,
-                min_increment,
-                anti_snipe_minutes,
-            } => {
-                assert_eq!(
-                    starting_bid,
-                    MoneyAmount::from_str(starting_bid_str).unwrap()
-                );
-                assert_eq!(
-                    buy_now_price,
-                    Some(MoneyAmount::from_str(buy_now_price_str).unwrap())
-                );
-                assert_eq!(
-                    min_increment,
-                    MoneyAmount::from_str(min_increment_str).unwrap(),
-                );
-                assert_eq!(anti_snipe_minutes, Some(5));
-            }
-            _ => panic!("Expected BasicAuction"),
-        }
+        let read_listing = listing_dao
+            .find_by_id(created_listing.persisted.id)
+            .await
+            .expect("Failed to find listing")
+            .expect("Listing should exist");
+
+        assert_eq!(read_listing, created_listing);
    }
 }
--- a/src/db/models/listing_type.rs
+++ b/src/db/models/listing_type.rs
@@ -1,14 +1,42 @@
+use std::fmt::Display;
+
 /// Types of listings supported by the platform
-#[derive(Debug, Clone, PartialEq, Eq, sqlx::Type)]
+#[derive(Debug, Clone, PartialEq, Eq, Copy, sqlx::Type)]
 #[sqlx(type_name = "TEXT")]
 #[sqlx(rename_all = "snake_case")]
 pub enum ListingType {
+    /// Fixed price sale with no bidding
+    FixedPriceListing,
    /// Traditional time-based auction with bidding
    BasicAuction,
    /// Auction with multiple winners/slots available
    MultiSlotAuction,
-    /// Fixed price sale with no bidding
-    FixedPriceListing,
    /// Blind auction where seller chooses winner
    BlindAuction,
 }
+
+impl ListingType {
+    pub fn as_str(&self) -> &'static str {
+        match self {
+            ListingType::FixedPriceListing => "Fixed Price Listing",
+            ListingType::BasicAuction => "Basic Auction",
+            ListingType::MultiSlotAuction => "Multi-Slot Auction",
+            ListingType::BlindAuction => "Blind Auction",
+        }
+    }
+
+    pub fn emoji_str(&self) -> &'static str {
+        match self {
+            ListingType::FixedPriceListing => "🛍️",
+            ListingType::BasicAuction => "⏰",
+            ListingType::MultiSlotAuction => "🎯",
+            ListingType::BlindAuction => "🎭",
+        }
+    }
+}
+
+impl Display for ListingType {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        write!(f, "{}", self.as_str())
+    }
+}
--- a/src/db/models/mod.rs
+++ b/src/db/models/mod.rs
@@ -2,12 +2,9 @@ pub mod bid;
 pub mod listing;
 pub mod listing_media;
 pub mod listing_type;
-pub mod new_listing;
 pub mod proxy_bid;
 pub mod user;
 pub mod user_settings;

 // Re-export all types for easy access
-pub use listing::*;
 pub use listing_type::*;
-pub use user::*;
--- a/src/db/models/new_listing.rs
+++ b/src/db/models/new_listing.rs
@@ -1,136 +0,0 @@
-use crate::db::{ListingType, MoneyAmount, UserRowId};
-use chrono::{DateTime, Utc};
-
-/// New listing data for insertion
-#[derive(Debug, Clone)]
-pub struct NewListing {
-    pub base: NewListingBase,
-    pub fields: NewListingFields,
-}
-
-impl NewListing {
-    pub fn listing_type(&self) -> ListingType {
-        match &self.fields {
-            NewListingFields::BasicAuction { .. } => ListingType::BasicAuction,
-            NewListingFields::MultiSlotAuction { .. } => ListingType::MultiSlotAuction,
-            NewListingFields::FixedPriceListing { .. } => ListingType::FixedPriceListing,
-            NewListingFields::BlindAuction { .. } => ListingType::BlindAuction,
-        }
-    }
-}
-
-#[derive(Debug, Clone)]
-pub struct NewListingBase {
-    pub seller_id: UserRowId,
-    pub title: String,
-    pub description: Option<String>,
-    pub starts_at: DateTime<Utc>,
-    pub ends_at: DateTime<Utc>,
-}
-
-#[derive(Debug, Clone)]
-#[allow(unused)]
-pub enum NewListingFields {
-    BasicAuction {
-        starting_bid: MoneyAmount,
-        buy_now_price: Option<MoneyAmount>,
-        min_increment: MoneyAmount,
-        anti_snipe_minutes: Option<i32>,
-    },
-    MultiSlotAuction {
-        starting_bid: MoneyAmount,
-        buy_now_price: MoneyAmount,
-        min_increment: Option<MoneyAmount>,
-        slots_available: i32,
-        anti_snipe_minutes: i32,
-    },
-    FixedPriceListing {
-        buy_now_price: MoneyAmount,
-        slots_available: i32,
-    },
-    BlindAuction {
-        starting_bid: MoneyAmount,
-    },
-}
-
-#[allow(unused)]
-impl NewListingBase {
-    pub fn new(
-        seller_id: UserRowId,
-        title: String,
-        description: Option<String>,
-        starts_at: DateTime<Utc>,
-        ends_at: DateTime<Utc>,
-    ) -> Self {
-        Self {
-            seller_id,
-            title,
-            description,
-            starts_at,
-            ends_at,
-        }
-    }
-
-    /// Create a new basic auction listing
-    pub fn new_basic_auction(
-        self,
-        starting_bid: MoneyAmount,
-        buy_now_price: Option<MoneyAmount>,
-        min_increment: MoneyAmount,
-        anti_snipe_minutes: Option<i32>,
-    ) -> NewListing {
-        NewListing {
-            base: self,
-            fields: NewListingFields::BasicAuction {
-                starting_bid,
-                buy_now_price,
-                min_increment,
-                anti_snipe_minutes,
-            },
-        }
-    }
-
-    /// Create a new multi-slot auction listing
-    pub fn new_multi_slot_auction(
-        self,
-        starting_bid: MoneyAmount,
-        buy_now_price: MoneyAmount,
-        min_increment: Option<MoneyAmount>,
-        slots_available: i32,
-        anti_snipe_minutes: i32,
-    ) -> NewListing {
-        NewListing {
-            base: self,
-            fields: NewListingFields::MultiSlotAuction {
-                starting_bid,
-                buy_now_price,
-                min_increment,
-                slots_available,
-                anti_snipe_minutes,
-            },
-        }
-    }
-
-    /// Create a new fixed price listing
-    pub fn new_fixed_price_listing(
-        self,
-        buy_now_price: MoneyAmount,
-        slots_available: i32,
-    ) -> NewListing {
-        NewListing {
-            base: self,
-            fields: NewListingFields::FixedPriceListing {
-                buy_now_price,
-                slots_available,
-            },
-        }
-    }
-
-    /// Create a new blind auction listing
-    pub fn new_blind_auction(self, starting_bid: MoneyAmount) -> NewListing {
-        NewListing {
-            base: self,
-            fields: NewListingFields::BlindAuction { starting_bid },
-        }
-    }
-}
--- a/src/db/models/user.rs
+++ b/src/db/models/user.rs
@@ -1,26 +1,44 @@
 use chrono::{DateTime, Utc};
 use sqlx::FromRow;
+use std::fmt::Debug;

-use crate::db::{TelegramUserId, UserRowId};
+use crate::db::{DbTelegramUserId, DbUserId};
+
+pub type PersistedUser = DbUser<PersistedUserFields>;
+pub type NewUser = DbUser<()>;

 /// Core user information
-#[derive(Debug, Clone, FromRow)]
+#[derive(Clone, FromRow, PartialEq)]
 #[allow(unused)]
-pub struct User {
-    pub id: UserRowId,
-    pub telegram_id: TelegramUserId,
+pub struct DbUser<P: Debug + Clone> {
+    pub persisted: P,
+    pub telegram_id: DbTelegramUserId,
+    pub first_name: String,
+    pub last_name: Option<String>,
    pub username: Option<String>,
-    pub display_name: Option<String>,
-    // SQLite stores booleans as INTEGER (0/1), sqlx FromRow handles the conversion automatically
    pub is_banned: bool,
+}
+
+impl Debug for DbUser<PersistedUserFields> {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        let name = if let Some(last_name) = self.last_name.as_deref() {
+            format!("{} {}", self.first_name, last_name)
+        } else {
+            self.first_name.clone()
+        };
+        let username = self.username.as_deref().unwrap_or("");
+        write!(
+            f,
+            "User(id: {} / {}, '{}' @{})",
+            self.persisted.id, self.telegram_id, name, username
+        )
+    }
+}
+
+#[derive(Debug, Clone, PartialEq)]
+#[allow(unused)]
+pub struct PersistedUserFields {
+    pub id: DbUserId,
    pub created_at: DateTime<Utc>,
    pub updated_at: DateTime<Utc>,
 }
-
-/// New user data for insertion
-#[derive(Debug, Clone)]
-pub struct NewUser {
-    pub telegram_id: TelegramUserId,
-    pub username: Option<String>,
-    pub display_name: Option<String>,
-}
--- a/src/db/types/currency_type.rs
+++ b/src/db/types/currency_type.rs
@@ -1,12 +1,17 @@
+use serde::{Deserialize, Serialize};
 use sqlx::{
    encode::IsNull, error::BoxDynError, sqlite::SqliteTypeInfo, Decode, Encode, Sqlite, Type,
 };

 /// Currency types supported by the platform
-#[derive(Debug, Clone, Copy, PartialEq, Eq, Default)]
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Default, Serialize, Deserialize)]
 pub enum CurrencyType {
    #[default]
-    Usd,
+    Usd, // United States Dollar
+    Cad, // Canadian Dollar
+    Gbp, // British Pound
+    Eur, // Euro
+    Jpy, // Japanese Yen
 }

 #[allow(unused)]
@@ -15,6 +20,10 @@ impl CurrencyType {
    pub fn as_str(&self) -> &'static str {
        match self {
            CurrencyType::Usd => "USD",
+            CurrencyType::Cad => "CAD",
+            CurrencyType::Gbp => "GBP",
+            CurrencyType::Eur => "EUR",
+            CurrencyType::Jpy => "JPY",
        }
    }

@@ -22,13 +31,24 @@ impl CurrencyType {
    pub fn symbol(&self) -> &'static str {
        match self {
            CurrencyType::Usd => "$",
+            CurrencyType::Cad => "$",
+            CurrencyType::Gbp => "£",
+            CurrencyType::Eur => "€",
+            CurrencyType::Jpy => "¥",
        }
    }
+}

-    /// Parse currency from string
-    pub fn from_str(s: &str) -> Result<Self, String> {
-        match s.to_uppercase().as_str() {
-            "USD" => Ok(CurrencyType::Usd),
+impl TryFrom<&str> for CurrencyType {
+    type Error = String;
+
+    fn try_from(s: &str) -> Result<Self, String> {
+        match s.to_uppercase().trim() {
+            "USD" | "US" | "$" => Ok(CurrencyType::Usd),
+            "CAD" | "CA" => Ok(CurrencyType::Cad),
+            "GBP" | "GB" | "£" => Ok(CurrencyType::Gbp),
+            "EUR" | "EU" | "€" => Ok(CurrencyType::Eur),
+            "JPY" | "JP" | "¥" => Ok(CurrencyType::Jpy),
            _ => Err(format!("Unsupported currency: {s}")),
        }
    }
@@ -70,13 +90,14 @@ impl<'q> Encode<'q, Sqlite> for CurrencyType {
 impl<'r> Decode<'r, Sqlite> for CurrencyType {
    fn decode(value: sqlx::sqlite::SqliteValueRef<'r>) -> Result<Self, BoxDynError> {
        let currency_str = <&str as Decode<Sqlite>>::decode(value)?;
-        CurrencyType::from_str(currency_str).map_err(Into::into)
+        CurrencyType::try_from(currency_str).map_err(Into::into)
    }
 }

 #[cfg(test)]
 mod tests {
    use super::*;
+    use rstest::rstest;

    #[test]
    fn test_currency_type_display() {
@@ -92,15 +113,20 @@ mod tests {
        assert_eq!(default_currency, CurrencyType::Usd);
    }

-    #[test]
-    fn test_currency_type_parsing() {
-        let parsed_currency = CurrencyType::from_str("usd").unwrap(); // Case insensitive
-        assert_eq!(parsed_currency, CurrencyType::Usd);
+    #[rstest]
+    #[case("usd", CurrencyType::Usd)]
+    #[case("USD", CurrencyType::Usd)]
+    #[case("USD", CurrencyType::Usd)]
+    #[case("CA", CurrencyType::Cad)]
+    fn test_currency_type_parsing(#[case] input: &str, #[case] expected: CurrencyType) {
+        let parsed_currency = CurrencyType::try_from(input).unwrap();
+        assert_eq!(parsed_currency, expected);
+    }

-        let parsed_upper = CurrencyType::from_str("USD").unwrap();
-        assert_eq!(parsed_upper, CurrencyType::Usd);
-
-        let invalid = CurrencyType::from_str("EUR");
+    #[rstest]
+    #[case("ASD")]
+    fn test_currency_type_parsing_invalid(#[case] input: &str) {
+        let invalid = CurrencyType::try_from(input);
        assert!(invalid.is_err());
    }
 }
--- a/src/db/types/db_id.rs
+++ b/src/db/types/db_id.rs
@@ -0,0 +1,99 @@
+use serde::{Deserialize, Serialize};
+use sqlx::{
+    encode::IsNull, error::BoxDynError, sqlite::SqliteTypeInfo, Decode, Encode, Sqlite, Type,
+};
+use std::fmt;
+
+macro_rules! impl_db_id {
+    ($id_name:ident, $id_type:ty) => {
+        #[doc = "Type-safe wrapper for "]
+        #[doc = stringify!($id_name)]
+        #[doc = " IDs"]
+        #[derive(
+            Debug, Clone, Copy, PartialEq, Eq, PartialOrd, Ord, Hash, Serialize, Deserialize,
+        )]
+        pub struct $id_name($id_type);
+
+        impl $id_name {
+            /// Create a new ListingId from an i64
+            pub fn new(id: $id_type) -> Self {
+                Self(id)
+            }
+
+            /// Get the inner i64 value
+            pub fn get(&self) -> $id_type {
+                self.0
+            }
+        }
+
+        impl From<$id_type> for $id_name {
+            fn from(id: $id_type) -> Self {
+                Self(id)
+            }
+        }
+
+        impl From<$id_name> for $id_type {
+            fn from(value: $id_name) -> Self {
+                value.0
+            }
+        }
+
+        impl fmt::Display for $id_name {
+            fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+                write!(f, "{}", self.0)
+            }
+        }
+
+        // SQLx implementations for database compatibility
+        impl Type<Sqlite> for $id_name {
+            fn type_info() -> SqliteTypeInfo {
+                <$id_type as Type<Sqlite>>::type_info()
+            }
+
+            fn compatible(ty: &SqliteTypeInfo) -> bool {
+                <$id_type as Type<Sqlite>>::compatible(ty)
+            }
+        }
+
+        impl<'q> Encode<'q, Sqlite> for $id_name {
+            fn encode_by_ref(
+                &self,
+                args: &mut Vec<sqlx::sqlite::SqliteArgumentValue<'q>>,
+            ) -> Result<IsNull, BoxDynError> {
+                <$id_type as Encode<'q, Sqlite>>::encode_by_ref(&self.0, args)
+            }
+        }
+
+        impl<'r> Decode<'r, Sqlite> for $id_name {
+            fn decode(value: sqlx::sqlite::SqliteValueRef<'r>) -> Result<Self, BoxDynError> {
+                let id = <$id_type as Decode<'r, Sqlite>>::decode(value)?;
+                Ok(Self(id))
+            }
+        }
+    };
+}
+
+impl_db_id!(DbBidId, i64);
+impl_db_id!(DbProxyBidId, i64);
+impl_db_id!(DbListingId, i64);
+impl_db_id!(DbUserId, i64);
+
+impl_db_id!(DbTelegramUserId, i64);
+
+impl From<teloxide::types::UserId> for DbTelegramUserId {
+    fn from(id: teloxide::types::UserId) -> Self {
+        Self(id.0 as i64)
+    }
+}
+
+impl From<DbTelegramUserId> for teloxide::types::UserId {
+    fn from(user_id: DbTelegramUserId) -> Self {
+        teloxide::types::UserId(user_id.0 as u64)
+    }
+}
+
+impl From<DbTelegramUserId> for teloxide::types::ChatId {
+    fn from(user_id: DbTelegramUserId) -> Self {
+        teloxide::types::ChatId(user_id.0)
+    }
+}
--- a/src/db/types/listing_id.rs
+++ b/src/db/types/listing_id.rs
@@ -1,71 +0,0 @@
-//! ListingId newtype for type-safe listing identification
-//!
-//! This newtype prevents accidentally mixing up listing IDs with other ID types
-//! while maintaining compatibility with the database layer through SQLx traits.
-
-use serde::{Deserialize, Serialize};
-use sqlx::{
-    encode::IsNull, error::BoxDynError, sqlite::SqliteTypeInfo, Decode, Encode, Sqlite, Type,
-};
-use std::fmt;
-
-/// Type-safe wrapper for listing IDs
-#[derive(Debug, Clone, Copy, PartialEq, Eq, PartialOrd, Ord, Hash, Serialize, Deserialize)]
-pub struct ListingId(i64);
-
-impl ListingId {
-    /// Create a new ListingId from an i64
-    pub fn new(id: i64) -> Self {
-        Self(id)
-    }
-
-    /// Get the inner i64 value
-    pub fn get(&self) -> i64 {
-        self.0
-    }
-}
-
-impl From<i64> for ListingId {
-    fn from(id: i64) -> Self {
-        Self(id)
-    }
-}
-
-impl From<ListingId> for i64 {
-    fn from(listing_id: ListingId) -> Self {
-        listing_id.0
-    }
-}
-
-impl fmt::Display for ListingId {
-    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        write!(f, "{}", self.0)
-    }
-}
-
-// SQLx implementations for database compatibility
-impl Type<Sqlite> for ListingId {
-    fn type_info() -> SqliteTypeInfo {
-        <i64 as Type<Sqlite>>::type_info()
-    }
-
-    fn compatible(ty: &SqliteTypeInfo) -> bool {
-        <i64 as Type<Sqlite>>::compatible(ty)
-    }
-}
-
-impl<'q> Encode<'q, Sqlite> for ListingId {
-    fn encode_by_ref(
-        &self,
-        args: &mut Vec<sqlx::sqlite::SqliteArgumentValue<'q>>,
-    ) -> Result<IsNull, BoxDynError> {
-        <i64 as Encode<'q, Sqlite>>::encode_by_ref(&self.0, args)
-    }
-}
-
-impl<'r> Decode<'r, Sqlite> for ListingId {
-    fn decode(value: sqlx::sqlite::SqliteValueRef<'r>) -> Result<Self, BoxDynError> {
-        let id = <i64 as Decode<'r, Sqlite>>::decode(value)?;
-        Ok(Self(id))
-    }
-}
--- a/src/db/types/mod.rs
+++ b/src/db/types/mod.rs
@@ -1,15 +1,13 @@
 mod currency_type;
+mod db_id;
 mod listing_duration;
-mod listing_id;
+mod money;
 mod money_amount;
-mod telegram_user_id;
-mod user_row_id;

 // Re-export all types for easy access
 #[allow(unused)]
 pub use currency_type::*;
+pub use db_id::*;
 pub use listing_duration::*;
-pub use listing_id::*;
+pub use money::*;
 pub use money_amount::*;
-pub use telegram_user_id::*;
-pub use user_row_id::*;
--- a/src/db/types/money.rs
+++ b/src/db/types/money.rs
@@ -0,0 +1,43 @@
+use crate::db::{CurrencyType, MoneyAmount};
+use serde::{Deserialize, Serialize};
+use std::fmt::Display;
+
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Serialize, Deserialize)]
+pub struct Money(CurrencyType, MoneyAmount);
+impl Money {
+    pub fn new(currency_type: CurrencyType, money_amount: MoneyAmount) -> Self {
+        Self(currency_type, money_amount)
+    }
+}
+impl PartialOrd for Money {
+    fn partial_cmp(&self, other: &Self) -> Option<std::cmp::Ordering> {
+        if self.0 != other.0 {
+            return None;
+        }
+        self.1.partial_cmp(&other.1)
+    }
+}
+impl Display for Money {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        write!(f, "{}{}", self.0.symbol(), self.1)
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use rstest::rstest;
+
+    #[rstest]
+    #[case("$100.00", CurrencyType::Usd, 100_00)]
+    #[case("¥100.00", CurrencyType::Jpy, 100_00)]
+    fn test_money_display(
+        #[case] expected: &str,
+        #[case] currency_type: CurrencyType,
+        #[case] amount_cents: i64,
+    ) {
+        let amount = MoneyAmount::from_cents(amount_cents);
+        let money = Money::new(currency_type, amount);
+        assert_eq!(money.to_string(), expected);
+    }
+}
--- a/src/db/types/money_amount.rs
+++ b/src/db/types/money_amount.rs
@@ -6,6 +6,8 @@ use sqlx::{
 use std::ops::{Add, Sub};
 use std::str::FromStr;

+use crate::db::{CurrencyType, Money};
+
 /// Newtype wrapper for monetary amounts stored as integer cents
 /// Stores as INTEGER in SQLite for precise comparisons and simple arithmetic
 #[derive(Debug, Clone, Copy, PartialEq, Eq, PartialOrd, Ord, Serialize, Deserialize)]
@@ -23,12 +25,6 @@ impl MoneyAmount {
        Self(cents)
    }

-    /// Create a MoneyAmount from a string representation (e.g., "12.34")
-    pub fn from_str(s: &str) -> Result<Self, rust_decimal::Error> {
-        let decimal = Decimal::from_str(s)?;
-        Ok(Self::new(decimal))
-    }
-
    /// Create a zero MoneyAmount
    pub fn zero() -> Self {
        Self(0)
@@ -43,6 +39,20 @@ impl MoneyAmount {
    pub fn to_decimal(self) -> Decimal {
        Decimal::new(self.0, 2) // 2 decimal places for cents
    }
+
+    pub fn with_type(self, currency_type: CurrencyType) -> Money {
+        Money::new(currency_type, self)
+    }
+}
+
+impl FromStr for MoneyAmount {
+    type Err = rust_decimal::Error;
+
+    /// Create a MoneyAmount from a string representation (e.g., "12.34")
+    fn from_str(s: &str) -> Result<Self, Self::Err> {
+        let decimal = Decimal::from_str(s)?;
+        Ok(Self::new(decimal))
+    }
 }

 impl Default for MoneyAmount {
@@ -203,7 +213,7 @@ mod tests {

        // Insert test data
        sqlx::query("INSERT INTO test_money (amount, currency) VALUES (?, ?)")
-            .bind(&amount)
+            .bind(amount)
            .bind(CurrencyType::Usd)
            .execute(&pool)
            .await
@@ -245,7 +255,7 @@ mod tests {
        sqlx::query("INSERT INTO test_money (amount, currency, optional_amount) VALUES (?, ?, ?)")
            .bind(MoneyAmount::from_str("100.00").unwrap())
            .bind(CurrencyType::Usd)
-            .bind(&optional_amount)
+            .bind(optional_amount)
            .execute(&pool)
            .await
            .expect("Failed to insert some optional amount");
@@ -290,7 +300,7 @@ mod tests {

        // Insert into database
        sqlx::query("INSERT INTO test_money (amount, currency) VALUES (?, ?)")
-            .bind(&amount)
+            .bind(amount)
            .bind(CurrencyType::Usd)
            .execute(&pool)
            .await
@@ -308,10 +318,7 @@ mod tests {
        assert_eq!(
            retrieved_amount.to_string(),
            expected_str,
-            "Cent-level precision not correct for input: {} (expected: {}, got: {})",
-            input_str,
-            expected_str,
-            retrieved_amount.to_string()
+            "Cent-level precision not correct for input: {input_str} (expected: {expected_str}, got: {retrieved_amount})"
        );
    }

@@ -478,10 +485,8 @@ mod tests {
        setup_test_data_for_queries(&pool).await;

        let threshold_amount = MoneyAmount::from_str(threshold).unwrap();
-        let query = format!(
-            "SELECT COUNT(*) as count FROM test_bids WHERE bid_amount {} ?",
-            operator
-        );
+        let query =
+            format!("SELECT COUNT(*) as count FROM test_bids WHERE bid_amount {operator} ?");

        let count_row = sqlx::query(&query)
            .bind(threshold_amount)
@@ -492,8 +497,7 @@ mod tests {
        let count: i64 = count_row.get("count");
        assert_eq!(
            count as usize, expected_count,
-            "Comparison {} {} failed",
-            operator, threshold
+            "Comparison {operator} {threshold} failed"
        );
    }

@@ -524,8 +528,7 @@ mod tests {
        let count: i64 = count_row.get("count");
        assert_eq!(
            count as usize, expected_count,
-            "BETWEEN {} AND {} failed",
-            min_amount, max_amount
+            "BETWEEN {min_amount} AND {max_amount} failed"
        );
    }

--- a/src/db/types/telegram_user_id.rs
+++ b/src/db/types/telegram_user_id.rs
@@ -1,78 +0,0 @@
-//! TelegramUserId
-//! newtype for type-safe user identification
-//!
-//! This newtype prevents accidentally mixing up user IDs with other ID types
-//! while maintaining compatibility with the database layer through SQLx traits.
-
-use sqlx::{
-    encode::IsNull, error::BoxDynError, sqlite::SqliteTypeInfo, Decode, Encode, Sqlite, Type,
-};
-use std::fmt;
-
-/// Type-safe wrapper for user IDs
-#[derive(Debug, Clone, Copy, PartialEq, Eq, PartialOrd, Ord, Hash)]
-pub struct TelegramUserId(teloxide::types::UserId);
-
-impl TelegramUserId {
-    /// Create a new TelegramUserId
-    /// from an i64
-    pub fn new(id: teloxide::types::UserId) -> Self {
-        Self(id)
-    }
-
-    /// Get the inner i64 value
-    pub fn get(&self) -> teloxide::types::UserId {
-        self.0
-    }
-}
-
-impl From<teloxide::types::UserId> for TelegramUserId {
-    fn from(id: teloxide::types::UserId) -> Self {
-        Self(id)
-    }
-}
-
-impl From<u64> for TelegramUserId {
-    fn from(id: u64) -> Self {
-        Self(teloxide::types::UserId(id))
-    }
-}
-
-impl From<TelegramUserId> for teloxide::types::UserId {
-    fn from(user_id: TelegramUserId) -> Self {
-        user_id.0
-    }
-}
-
-impl fmt::Display for TelegramUserId {
-    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        write!(f, "{}", self.0)
-    }
-}
-
-// SQLx implementations for database compatibility
-impl Type<Sqlite> for TelegramUserId {
-    fn type_info() -> SqliteTypeInfo {
-        <i64 as Type<Sqlite>>::type_info()
-    }
-
-    fn compatible(ty: &SqliteTypeInfo) -> bool {
-        <i64 as Type<Sqlite>>::compatible(ty)
-    }
-}
-
-impl<'q> Encode<'q, Sqlite> for TelegramUserId {
-    fn encode_by_ref(
-        &self,
-        args: &mut Vec<sqlx::sqlite::SqliteArgumentValue<'q>>,
-    ) -> Result<IsNull, BoxDynError> {
-        <i64 as Encode<'q, Sqlite>>::encode(self.0 .0 as i64, args)
-    }
-}
-
-impl<'r> Decode<'r, Sqlite> for TelegramUserId {
-    fn decode(value: sqlx::sqlite::SqliteValueRef<'r>) -> Result<Self, BoxDynError> {
-        let id = <i64 as Decode<'r, Sqlite>>::decode(value)?;
-        Ok(Self(teloxide::types::UserId(id as u64)))
-    }
-}
--- a/src/db/types/user_row_id.rs
+++ b/src/db/types/user_row_id.rs
@@ -1,70 +0,0 @@
-//! UserId newtype for type-safe user identification
-//!
-//! This newtype prevents accidentally mixing up user IDs with other ID types
-//! while maintaining compatibility with the database layer through SQLx traits.
-
-use sqlx::{
-    encode::IsNull, error::BoxDynError, sqlite::SqliteTypeInfo, Decode, Encode, Sqlite, Type,
-};
-use std::fmt;
-
-/// Type-safe wrapper for user IDs
-#[derive(Debug, Clone, Copy, PartialEq, Eq, PartialOrd, Ord, Hash)]
-pub struct UserRowId(i64);
-
-impl UserRowId {
-    /// Create a new UserId from an i64
-    pub fn new(id: i64) -> Self {
-        Self(id)
-    }
-
-    /// Get the inner i64 value
-    pub fn get(&self) -> i64 {
-        self.0
-    }
-}
-
-impl From<i64> for UserRowId {
-    fn from(id: i64) -> Self {
-        Self(id)
-    }
-}
-
-impl From<UserRowId> for i64 {
-    fn from(user_id: UserRowId) -> Self {
-        user_id.0
-    }
-}
-
-impl fmt::Display for UserRowId {
-    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        write!(f, "{}", self.0)
-    }
-}
-
-// SQLx implementations for database compatibility
-impl Type<Sqlite> for UserRowId {
-    fn type_info() -> SqliteTypeInfo {
-        <i64 as Type<Sqlite>>::type_info()
-    }
-
-    fn compatible(ty: &SqliteTypeInfo) -> bool {
-        <i64 as Type<Sqlite>>::compatible(ty)
-    }
-}
-
-impl<'q> Encode<'q, Sqlite> for UserRowId {
-    fn encode_by_ref(
-        &self,
-        args: &mut Vec<sqlx::sqlite::SqliteArgumentValue<'q>>,
-    ) -> Result<IsNull, BoxDynError> {
-        <i64 as Encode<'q, Sqlite>>::encode_by_ref(&self.0, args)
-    }
-}
-
-impl<'r> Decode<'r, Sqlite> for UserRowId {
-    fn decode(value: sqlx::sqlite::SqliteValueRef<'r>) -> Result<Self, BoxDynError> {
-        let id = <i64 as Decode<'r, Sqlite>>::decode(value)?;
-        Ok(Self(id))
-    }
-}
--- a/src/dptree_utils.rs
+++ b/src/dptree_utils.rs
@@ -1,3 +1,10 @@
+use std::{collections::BTreeSet, ops::ControlFlow, sync::Arc};
+
+use dptree::{
+    di::{Asyncify, Injectable},
+    from_fn_with_description, Handler, HandlerDescription, HandlerSignature, Type,
+};
+
 #[macro_export]
 macro_rules! case {
    // Basic variant matching without parameters
@@ -72,6 +79,66 @@ macro_rules! case {
    };
 }

+pub trait MapTwo<'a, Output, Descr> {
+    #[must_use]
+    #[track_caller]
+    fn map2<Proj, NewType1, NewType2, Args>(self, proj: Proj) -> Handler<'a, Output, Descr>
+    where
+        Asyncify<Proj>: Injectable<(NewType1, NewType2), Args> + Send + Sync + 'a,
+        NewType1: Send + Sync + 'static,
+        NewType2: Send + Sync + 'static;
+}
+
+impl<'a, Output, Descr> MapTwo<'a, Output, Descr> for Handler<'a, Output, Descr>
+where
+    Output: 'a,
+    Descr: HandlerDescription,
+{
+    fn map2<Proj, NewType1, NewType2, Args>(self, proj: Proj) -> Handler<'a, Output, Descr>
+    where
+        Asyncify<Proj>: Injectable<(NewType1, NewType2), Args> + Send + Sync + 'a,
+        NewType1: Send + Sync + 'static,
+        NewType2: Send + Sync + 'static,
+    {
+        let proj = Arc::new(Asyncify(proj));
+
+        self.chain(from_fn_with_description(
+            Descr::map(),
+            move |container, cont| {
+                let proj = Arc::clone(&proj);
+
+                async move {
+                    let proj = proj.inject(&container);
+                    let (res1, res2) = proj().await;
+                    std::mem::drop(proj);
+
+                    let mut intermediate = container.clone();
+                    intermediate.insert(res1);
+                    intermediate.insert(res2);
+                    match cont(intermediate).await {
+                        ControlFlow::Continue(_) => ControlFlow::Continue(container),
+                        ControlFlow::Break(result) => ControlFlow::Break(result),
+                    }
+                }
+            },
+            HandlerSignature::Other {
+                obligations:
+                    <Asyncify<Proj> as Injectable<(NewType1, NewType2), Args>>::obligations(),
+                guaranteed_outcomes: BTreeSet::from_iter(vec![
+                    Type::of::<NewType1>(),
+                    Type::of::<NewType2>(),
+                ]),
+                conditional_outcomes: BTreeSet::new(),
+                continues: true,
+            },
+        ))
+    }
+}
+
+pub fn identity<T>(t: T) -> T {
+    t
+}
+
 #[cfg(test)]
 mod tests {
    use std::ops::ControlFlow;
@@ -94,11 +161,11 @@ mod tests {

    #[derive(Debug, Clone, PartialEq)]
    enum InnerEnum {
-        InnerSimple,
-        InnerWithParam(&'static str),
-        InnerWithMultiple(&'static str, i32),
-        InnerWithStruct { field: &'static str },
-        InnerWithMultiStruct { field: &'static str, number: i32 },
+        Simple,
+        WithParam(&'static str),
+        WithMultiple(&'static str, i32),
+        WithStruct { field: &'static str },
+        WithMultiStruct { field: &'static str, number: i32 },
    }

    // Helper function for testing handlers with expected results
@@ -144,29 +211,29 @@ mod tests {
    )]
    // Single parameter extraction from nested enum
    #[case::nested_single_match(
-        case![TestEnum::NestedVariant(InnerEnum::InnerWithParam(p))].endpoint(|p: &'static str| async move { p }),
-        TestEnum::NestedVariant(InnerEnum::InnerWithParam("nested")),
+        case![TestEnum::NestedVariant(InnerEnum::WithParam(p))].endpoint(|p: &'static str| async move { p }),
+        TestEnum::NestedVariant(InnerEnum::WithParam("nested")),
        Some("nested")
    )]
    #[case::nested_single_wrong_inner_variant(
-        case![TestEnum::NestedVariant(InnerEnum::InnerWithParam(p))].endpoint(|p: &'static str| async move { p }),
-        TestEnum::NestedVariant(InnerEnum::InnerSimple),
+        case![TestEnum::NestedVariant(InnerEnum::WithParam(p))].endpoint(|p: &'static str| async move { p }),
+        TestEnum::NestedVariant(InnerEnum::Simple),
        None
    )]
    #[case::nested_single_wrong_outer_variant(
-        case![TestEnum::NestedVariant(InnerEnum::InnerWithParam(p))].endpoint(|p: &'static str| async move { p }),
+        case![TestEnum::NestedVariant(InnerEnum::WithParam(p))].endpoint(|p: &'static str| async move { p }),
        TestEnum::DefaultVariant,
        None
    )]
    // Single field extraction from nested struct
    #[case::struct_field_match(
-        case![TestEnum::NestedVariant(InnerEnum::InnerWithStruct { field })].endpoint(|field: &'static str| async move { field }),
-        TestEnum::NestedVariant(InnerEnum::InnerWithStruct { field: "struct_value" }),
+        case![TestEnum::NestedVariant(InnerEnum::WithStruct { field })].endpoint(|field: &'static str| async move { field }),
+        TestEnum::NestedVariant(InnerEnum::WithStruct { field: "struct_value" }),
        Some("struct_value")
    )]
    #[case::struct_field_no_match(
-        case![TestEnum::NestedVariant(InnerEnum::InnerWithStruct { field })].endpoint(|field: &'static str| async move { field }),
-        TestEnum::NestedVariant(InnerEnum::InnerSimple),
+        case![TestEnum::NestedVariant(InnerEnum::WithStruct { field })].endpoint(|field: &'static str| async move { field }),
+        TestEnum::NestedVariant(InnerEnum::Simple),
        None
    )]
    #[tokio::test]
@@ -202,8 +269,8 @@ mod tests {

    // Test cases for nested multiple parameter extraction
    #[rstest::rstest]
-    #[case(TestEnum::NestedVariant(InnerEnum::InnerWithMultiple("nested", 123)), Some(("nested", 123)))]
-    #[case(TestEnum::NestedVariant(InnerEnum::InnerSimple), None)]
+    #[case(TestEnum::NestedVariant(InnerEnum::WithMultiple("nested", 123)), Some(("nested", 123)))]
+    #[case(TestEnum::NestedVariant(InnerEnum::Simple), None)]
    #[case(TestEnum::DefaultVariant, None)]
    #[tokio::test]
    async fn test_nested_multiple_parameter_extraction(
@@ -211,7 +278,7 @@ mod tests {
        #[case] expected_params: Option<(&'static str, i32)>,
    ) {
        let handler: Handler<'static, (&str, i32), DpHandlerDescription> =
-            case![TestEnum::NestedVariant(InnerEnum::InnerWithMultiple(s, n))]
+            case![TestEnum::NestedVariant(InnerEnum::WithMultiple(s, n))]
                .endpoint(|params: (&'static str, i32)| async move { params });

        let input = deps![input_variant];
@@ -225,8 +292,8 @@ mod tests {

    // Test cases for struct pattern extraction
    #[rstest::rstest]
-    #[case(TestEnum::NestedVariant(InnerEnum::InnerWithStruct { field: "struct_field" }), Some("struct_field"))]
-    #[case(TestEnum::NestedVariant(InnerEnum::InnerSimple), None)]
+    #[case(TestEnum::NestedVariant(InnerEnum::WithStruct { field: "struct_field" }), Some("struct_field"))]
+    #[case(TestEnum::NestedVariant(InnerEnum::Simple), None)]
    #[case(TestEnum::DefaultVariant, None)]
    #[tokio::test]
    async fn test_struct_pattern_extraction(
@@ -234,10 +301,8 @@ mod tests {
        #[case] expected_field: Option<&'static str>,
    ) {
        let handler: Handler<'static, &str, DpHandlerDescription> =
-            case![TestEnum::NestedVariant(InnerEnum::InnerWithStruct {
-                field
-            })]
-            .endpoint(|field: &'static str| async move { field });
+            case![TestEnum::NestedVariant(InnerEnum::WithStruct { field })]
+                .endpoint(|field: &'static str| async move { field });

        let input = deps![input_variant];
        let result = handler.dispatch(input).await;
@@ -250,8 +315,8 @@ mod tests {

    // Test cases for multi-field struct pattern extraction
    #[rstest::rstest]
-    #[case(TestEnum::NestedVariant(InnerEnum::InnerWithMultiStruct { field: "multi_field", number: 42 }), Some(("multi_field", 42)))]
-    #[case(TestEnum::NestedVariant(InnerEnum::InnerSimple), None)]
+    #[case(TestEnum::NestedVariant(InnerEnum::WithMultiStruct { field: "multi_field", number: 42 }), Some(("multi_field", 42)))]
+    #[case(TestEnum::NestedVariant(InnerEnum::Simple), None)]
    #[case(TestEnum::DefaultVariant, None)]
    #[tokio::test]
    async fn test_multi_struct_pattern_extraction(
@@ -259,7 +324,7 @@ mod tests {
        #[case] expected_fields: Option<(&'static str, i32)>,
    ) {
        let handler: Handler<'static, (&str, i32), DpHandlerDescription> =
-            case![TestEnum::NestedVariant(InnerEnum::InnerWithMultiStruct {
+            case![TestEnum::NestedVariant(InnerEnum::WithMultiStruct {
                field,
                number
            })]
--- a/src/handle_error.rs
+++ b/src/handle_error.rs
@@ -0,0 +1,36 @@
+use crate::{wrap_endpoint, App, BotError, BotResult, WrappedAsyncFn};
+use futures::future::BoxFuture;
+
+pub async fn handle_error(app: App, error: BotError) -> BotResult {
+    log::error!("Error in handler: {error:?}");
+    match error {
+        BotError::UserVisibleError(message) => app.bot.send_html_message(message, None).await?,
+        BotError::InternalError(_) => {
+            app.bot
+                .send_html_message(
+                    "An internal error occurred. Please try again later.".to_string(),
+                    None,
+                )
+                .await?;
+        }
+    }
+    Ok(())
+}
+
+fn boxed_handle_error(app: App, error: BotError) -> BoxFuture<'static, BotResult> {
+    Box::pin(handle_error(app, error))
+}
+
+pub type ErrorHandlerWrapped<FnBase, FnBaseArgs> = WrappedAsyncFn<
+    FnBase,
+    fn(App, BotError) -> BoxFuture<'static, BotResult>,
+    BotError,
+    FnBaseArgs,
+    (App,),
+>;
+
+pub fn with_error_handler<FnBase, FnBaseArgs>(
+    handler: FnBase,
+) -> ErrorHandlerWrapped<FnBase, FnBaseArgs> {
+    wrap_endpoint(handler, boxed_handle_error)
+}
--- a/src/handler_utils.rs
+++ b/src/handler_utils.rs
@@ -0,0 +1,60 @@
+use log::warn;
+use teloxide::types::Update;
+
+use crate::{
+    db::{listing::PersistedListing, user::PersistedUser, DbListingId, ListingDAO, UserDAO},
+    MessageTarget,
+};
+
+pub async fn find_or_create_db_user_from_update(
+    user_dao: UserDAO,
+    update: Update,
+) -> Option<PersistedUser> {
+    let user = update.from()?.clone();
+    find_or_create_db_user(user_dao, user).await
+}
+
+pub async fn find_or_create_db_user(
+    user_dao: UserDAO,
+    user: teloxide::types::User,
+) -> Option<PersistedUser> {
+    match user_dao.find_or_create_by_telegram_user(user).await {
+        Ok(user) => {
+            log::debug!("loaded user from db: {user:?}");
+            Some(user)
+        }
+        Err(e) => {
+            log::error!("Error finding or creating user: {e}");
+            None
+        }
+    }
+}
+
+pub async fn find_listing_by_id(
+    listing_dao: ListingDAO,
+    listing_id: DbListingId,
+) -> Option<PersistedListing> {
+    listing_dao.find_by_id(listing_id).await.unwrap_or(None)
+}
+
+pub fn update_into_message_target(update: Update) -> Option<MessageTarget> {
+    match update.kind {
+        teloxide::types::UpdateKind::Message(message) => Some(message.chat.into()),
+        teloxide::types::UpdateKind::InlineQuery(inline_query) => Some(inline_query.from.into()),
+        teloxide::types::UpdateKind::CallbackQuery(callback_query) => {
+            (&callback_query).try_into().ok()
+        }
+        _ => {
+            warn!("Received unexpected update kind: {update:?}");
+            None
+        }
+    }
+}
+
+// pub fn message_into_message_target(message: Message) -> MessageTarget {
+//     message.chat.id.into()
+// }
+
+// pub fn callback_query_into_message_target(callback_query: CallbackQuery) -> Option<MessageTarget> {
+//     (&callback_query).try_into().ok()
+// }
--- a/src/keyboard_utils.rs
+++ b/src/keyboard_utils.rs
@@ -1,19 +1,19 @@
 #[macro_export]
 macro_rules! keyboard_buttons {
    ($vis:vis enum $name:ident {
-            $($variant:ident($text:literal, $callback_data:literal),)*
+            $($variant:ident($text:literal, $callback_data:literal)),* $(,)?
    }) => {
        keyboard_buttons! {
            $vis enum $name {
-                [$($variant($text, $callback_data),)*]
+                [$($variant($text, $callback_data)),*]
            }
        }
    };

    ($vis:vis enum $name:ident {
        $([
-            $($variant:ident($text:literal, $callback_data:literal),)*
-        ]),*
+            $($variant:ident($text:literal, $callback_data:literal)),* $(,)?
+        ]),* $(,)?
    }) => {
        #[derive(Debug, Clone, Copy, PartialEq, Eq)]
        $vis enum $name {
@@ -34,6 +34,34 @@ macro_rules! keyboard_buttons {
                )*
                markup
            }
+
+            #[allow(unused)]
+            pub fn to_button(self) -> teloxide::types::InlineKeyboardButton {
+                match self {
+                    $($($name::$variant => teloxide::types::InlineKeyboardButton::callback($text, $callback_data)),*),*
+                }
+            }
+
+            #[allow(unused)]
+            pub fn to_switch_inline_query(self) -> teloxide::types::InlineKeyboardButton {
+                match self {
+                    $($($name::$variant => teloxide::types::InlineKeyboardButton::switch_inline_query($text, $callback_data)),*),*
+                }
+            }
+
+            #[allow(unused)]
+            pub fn title(self) -> &'static str {
+                match self {
+                    $($($name::$variant => $text),*),*
+                }
+            }
+
+            #[allow(unused)]
+            pub fn callback_data(self) -> &'static str {
+                match self {
+                    $($($name::$variant => $callback_data),*),*
+                }
+            }
        }
        impl From<$name> for teloxide::types::InlineKeyboardButton {
            fn from(value: $name) -> Self {
@@ -43,13 +71,13 @@ macro_rules! keyboard_buttons {
            }
        }
        impl<'a> TryFrom<&'a str> for $name {
-            type Error = &'a str;
+            type Error = anyhow::Error;
            fn try_from(value: &'a str) -> Result<Self, Self::Error> {
                match value {
                    $($(
                        $callback_data => Ok(Self::$variant),
                    )*)*
-                    _ => Err(value),
+                    _ => anyhow::bail!("Unknown {name} button: {value}", name = stringify!($name)),
                }
            }
        }
--- a/src/listing_expiry_checker_task.rs
+++ b/src/listing_expiry_checker_task.rs
@@ -0,0 +1,271 @@
+use chrono::{DateTime, Duration, Utc};
+use std::collections::VecDeque;
+use tokio::sync::mpsc::Receiver;
+
+use crate::{
+    db::{dao::ListingUpdatedEvent, listing::PersistedListing, DAOs},
+    *,
+};
+
+pub async fn task(
+    message_sender: BoxedMessageSender,
+    daos: DAOs,
+    mut listing_event: Receiver<ListingUpdatedEvent>,
+) -> BotResult<()> {
+    const ERROR_WINDOW: Duration = Duration::seconds(3);
+    const COOLDOWN_DELAY: Duration = Duration::seconds(3);
+
+    let mut error_timestamps: VecDeque<DateTime<Utc>> = VecDeque::new();
+
+    loop {
+        match task_impl(&message_sender, &daos, &mut listing_event).await {
+            Ok(r) => return Ok(r),
+            Err(e) => {
+                log::error!("Error in listing expiry checker task: {e}");
+
+                let now = Utc::now();
+                error_timestamps.push_back(now);
+
+                // Remove errors older than the error window
+                while let Some(&front_time) = error_timestamps.front() {
+                    if now - front_time > ERROR_WINDOW {
+                        error_timestamps.pop_front();
+                    } else {
+                        break;
+                    }
+                }
+
+                // If we have 2 or more errors within the window, apply cooldown
+                if error_timestamps.len() >= 2 {
+                    log::warn!(
+                        "Multiple errors ({}) within {} seconds, applying cooldown of {} seconds",
+                        error_timestamps.len(),
+                        ERROR_WINDOW.num_seconds(),
+                        COOLDOWN_DELAY.num_seconds()
+                    );
+
+                    tokio::time::sleep(COOLDOWN_DELAY.to_std().map_err(BotError::internal)?).await;
+                }
+
+                continue;
+            }
+        }
+    }
+}
+
+async fn task_impl(
+    message_sender: &BoxedMessageSender,
+    daos: &DAOs,
+    listing_event: &mut Receiver<ListingUpdatedEvent>,
+) -> BotResult<()> {
+    const MAX_CHECK_INTERVAL: Duration = Duration::seconds(10);
+
+    loop {
+        let check_again_in =
+            if let Some(listing) = daos.listing.find_next_ending_listing().await? {
+                if handle_listing_expiry(message_sender, daos, &listing).await? {
+                    // if this listing was expired, immediately check again on the next listing
+                    continue;
+                }
+                // wait until the listing ends, or a listing is updated
+                (Utc::now() - listing.base.ends_at).clamp(Duration::zero(), MAX_CHECK_INTERVAL)
+            } else {
+                MAX_CHECK_INTERVAL
+            }
+            .to_std()
+            .map_err(BotError::internal)?;
+
+        tokio::select! {
+            _ = listing_event.recv() => {
+                log::info!("listing updated, rechecking expiry");
+                continue;
+            }
+            _ = tokio::time::sleep(check_again_in) => {
+                log::info!("listing expired or timeout, rechecking expiry");
+                continue;
+            },
+        }
+    }
+}
+
+async fn handle_listing_expiry(
+    message_sender: &BoxedMessageSender,
+    daos: &DAOs,
+    listing: &PersistedListing,
+) -> BotResult<bool> {
+    if listing.base.ends_at < Utc::now() {
+        let expired_ago = Utc::now() - listing.base.ends_at;
+        log::info!(
+            "listing expired: {listing_id} (expired {expired_ago} ago)",
+            listing_id = listing.persisted.id,
+        );
+        let listing = daos
+            .listing
+            .set_listing_is_active(listing.persisted.id, false)
+            .await?;
+
+        let seller = daos
+            .user
+            .find_by_id(listing.base.seller_id)
+            .await?
+            .ok_or(BotError::internal_str("Seller not found"))?;
+
+        let bids = daos.bid.bids_for_listing(listing.persisted.id).await?;
+
+        if let Some(bid) = bids.first() {
+            let buyer = daos
+                .user
+                .find_by_id(bid.buyer_id)
+                .await?
+                .ok_or(BotError::internal_str("Winning buyer not found"))?;
+
+            message_sender
+                .send_message(MessageType::UserHasWonListingForBuyer {
+                    listing: listing.clone(),
+                    buyer: buyer.clone(),
+                    seller: seller.clone(),
+                    bid: bid.clone(),
+                })
+                .await?;
+
+            message_sender
+                .send_message(MessageType::UserHasWonListingForSeller {
+                    listing: listing.clone(),
+                    buyer: buyer.clone(),
+                    seller: seller.clone(),
+                    bid: bid.clone(),
+                })
+                .await?;
+
+            // send message to all other buyers who did not win
+            for bid in bids.iter() {
+                if bid.buyer_id == buyer.persisted.id {
+                    continue;
+                }
+                let buyer = daos
+                    .user
+                    .find_by_id(bid.buyer_id)
+                    .await?
+                    .ok_or(BotError::internal_str("Losing buyer not found"))?;
+                message_sender
+                    .send_message(MessageType::UserHasLostListingForBuyer {
+                        listing: listing.clone(),
+                        buyer: buyer.clone(),
+                        seller: seller.clone(),
+                    })
+                    .await?;
+            }
+        } else {
+            // there was no winner, send notification to the seller
+            message_sender
+                .send_message(MessageType::ListingExpiredWithNoWinnerForSeller {
+                    listing: listing.clone(),
+                    seller: seller.clone(),
+                })
+                .await?;
+        }
+
+        return Ok(true);
+    }
+    Ok(false)
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::db::bid::NewBid;
+    use crate::db::MoneyAmount;
+    use crate::message_sender::MockMessageSender;
+    use crate::test_utils::*;
+    use mockall::predicate::function;
+    use std::str::FromStr;
+
+    #[tokio::test]
+    async fn test_listing_expiry() {
+        let Deps { deps, .. } = create_deps().await;
+        let seller = with_test_user(&deps, |user| {
+            user.telegram_id = 123.into();
+            user.username = Some("seller".to_string())
+        })
+        .await;
+        let losing_buyer = with_test_user(&deps, |user| {
+            user.telegram_id = 789.into();
+            user.username = Some("losing_buyer".to_string())
+        })
+        .await;
+        let winning_buyer = with_test_user(&deps, |user| {
+            user.telegram_id = 456.into();
+            user.username = Some("buyer".to_string())
+        })
+        .await;
+        let listing = with_test_listing(&deps, &seller, |listing| {
+            listing.base.ends_at = Utc::now() - Duration::seconds(1);
+        })
+        .await;
+
+        // the losing bid
+        deps.get::<DAOs>()
+            .bid
+            .insert_bid(&NewBid::new_basic(
+                listing.persisted.id,
+                losing_buyer.persisted.id,
+                MoneyAmount::from_str("50.00").unwrap(),
+            ))
+            .await
+            .unwrap();
+
+        // the winning bid
+        deps.get::<DAOs>()
+            .bid
+            .insert_bid(&NewBid::new_basic(
+                listing.persisted.id,
+                winning_buyer.persisted.id,
+                MoneyAmount::from_str("100.00").unwrap(),
+            ))
+            .await
+            .unwrap();
+
+        let winner_id = winning_buyer.persisted.id;
+        let loser_id = losing_buyer.persisted.id;
+        let mut message_sender = MockMessageSender::new();
+
+        message_sender
+            .expect_send_message()
+            .with(function(move |m| match m {
+                MessageType::UserHasWonListingForSeller { buyer, .. } => {
+                    buyer.persisted.id == winner_id
+                }
+                _ => false,
+            }))
+            .times(1)
+            .returning(|_| Ok(()));
+
+        message_sender
+            .expect_send_message()
+            .with(function(move |m| match m {
+                MessageType::UserHasWonListingForBuyer { buyer, .. } => {
+                    buyer.persisted.id == winner_id
+                }
+                _ => false,
+            }))
+            .times(1)
+            .returning(|_| Ok(()));
+
+        message_sender
+            .expect_send_message()
+            .with(function(move |m| match m {
+                MessageType::UserHasLostListingForBuyer { buyer, .. } => {
+                    buyer.persisted.id == loser_id
+                }
+                _ => false,
+            }))
+            .times(1)
+            .returning(|_| Ok(()));
+
+        let daos = (*deps.get::<DAOs>()).clone();
+        let message_sender: BoxedMessageSender = Box::new(message_sender);
+        handle_listing_expiry(&message_sender, &daos, &listing)
+            .await
+            .unwrap();
+    }
+}
--- a/src/main.rs
+++ b/src/main.rs
@@ -1,28 +1,86 @@
+mod bidding;
+mod bot_message_sender;
+mod bot_result;
 mod commands;
 mod config;
 mod db;
 mod dptree_utils;
+mod handle_error;
+mod handler_utils;
 mod keyboard_utils;
+mod listing_expiry_checker_task;
+mod message;
+mod message_sender;
+mod message_target;
 mod message_utils;
 mod sqlite_storage;
+mod start_command_data;
 #[cfg(test)]
 mod test_utils;
+mod wrap_endpoint;

+use std::sync::Arc;
+
+use crate::bidding::{bidding_handler, BiddingState};
+use crate::bot_message_sender::BotMessageSender;
 use crate::commands::{
-    my_listings::{my_listings_handler, MyListingsState},
+    my_listings::{my_listings_handler, my_listings_inline_handler, MyListingsState},
    new_listing::{new_listing_handler, NewListingState},
 };
+use crate::db::user::PersistedUser;
+use crate::db::{DAOs, ListingEventSender};
+use crate::handle_error::with_error_handler;
+use crate::handler_utils::{find_or_create_db_user_from_update, update_into_message_target};
+use crate::message::MessageType;
+use crate::message_sender::BoxedMessageSender;
 use crate::sqlite_storage::SqliteStorage;
-use anyhow::Result;
+use crate::start_command_data::StartCommandData;
+use anyhow::{anyhow, Result};
+pub use bot_result::*;
+use chrono::{Duration, Utc};
 use commands::*;
 use config::Config;
 use log::info;
+pub use message_target::MessageTarget;
 use serde::{Deserialize, Serialize};
-use teloxide::dispatching::{dialogue::serializer::Json, DpHandlerDescription};
+use teloxide::dispatching::dialogue::serializer::Json;
+use teloxide::types::Me;
 use teloxide::{prelude::*, types::BotCommand, utils::command::BotCommands};
+pub use wrap_endpoint::*;

-pub type HandlerResult<T = ()> = anyhow::Result<T>;
-pub type Handler = dptree::Handler<'static, HandlerResult, DpHandlerDescription>;
+#[derive(Clone)]
+pub struct App {
+    pub bot: Arc<BoxedMessageSender>,
+    pub daos: DAOs,
+    pub bot_username: String,
+}
+
+impl App {
+    pub fn new(bot: BoxedMessageSender, daos: DAOs, bot_username: String) -> Self {
+        Self {
+            bot: Arc::new(bot),
+            daos,
+            bot_username,
+        }
+    }
+
+    pub fn url_for_start_command(&self, command: StartCommandData) -> reqwest::Url {
+        format!(
+            "tg://resolve?domain={}&start={}",
+            self.bot_username,
+            command.encode_for_start_command()
+        )
+        .parse()
+        .unwrap()
+    }
+
+    pub async fn send_message(&self, message: MessageType) -> BotResult {
+        self.bot.send_message(message).await
+    }
+}
+
+#[derive(Debug, Clone)]
+struct BotUsername(String);

 /// Set up the bot's command menu that appears when users tap the menu button
 async fn setup_bot_commands(bot: &Bot) -> Result<()> {
@@ -62,12 +120,61 @@ pub enum Command {
 enum DialogueRootState {
    #[default]
    Start,
+    MainMenu,
    NewListing(NewListingState),
    MyListings(MyListingsState),
+    Bidding(BiddingState),
 }

 type RootDialogue = Dialogue<DialogueRootState, SqliteStorage<Json>>;

+pub fn main_handler() -> BotHandler {
+    dptree::entry()
+        .map(|daos: DAOs| daos.user.clone())
+        .map(|daos: DAOs| daos.listing.clone())
+        .map(|daos: DAOs| daos.bid.clone())
+        .filter_map_async(find_or_create_db_user_from_update)
+        .branch(
+            Update::filter_message()
+                .filter(filter_forwarded_from_pawctioneer_bot)
+                .endpoint(handle_forwarded_from_pawctioneer_bot),
+        )
+        .branch(my_listings_inline_handler())
+        .branch(
+            dptree::entry()
+                .enter_dialogue::<Update, SqliteStorage<Json>, DialogueRootState>()
+                .branch(new_listing_handler())
+                .branch(my_listings_handler())
+                .branch(bidding_handler())
+                .branch(
+                    Update::filter_callback_query().branch(
+                        dptree::case![DialogueRootState::MainMenu]
+                            .endpoint(with_error_handler(handle_main_menu_callback)),
+                    ),
+                )
+                .branch(
+                    Update::filter_message()
+                        .filter_command::<Command>()
+                        .branch(
+                            dptree::case![Command::Start]
+                                .endpoint(with_error_handler(handle_start)),
+                        )
+                        .branch(
+                            dptree::case![Command::Help].endpoint(with_error_handler(handle_help)),
+                        )
+                        .branch(
+                            dptree::case![Command::MyBids]
+                                .endpoint(with_error_handler(handle_my_bids)),
+                        )
+                        .branch(
+                            dptree::case![Command::Settings]
+                                .endpoint(with_error_handler(handle_settings)),
+                        ),
+                ),
+        )
+        .branch(Update::filter_message().endpoint(with_error_handler(unknown_message_handler)))
+}
+
 #[tokio::main]
 async fn main() -> Result<()> {
    // Load and validate configuration from environment/.env file
@@ -77,53 +184,108 @@ async fn main() -> Result<()> {
    let db_pool = config.create_database_pool().await?;

    info!("Starting Pawctioneer Bot...");
-    let bot = Bot::new(&config.telegram_token);
+    let bot = Box::new(Bot::new(&config.telegram_token));
+
+    // set up the listing expiry checker task
+    let (listing_expiry_checker_tx, listing_expiry_checker_rx) = ListingEventSender::channel();
+    let daos = DAOs::new(db_pool.clone(), listing_expiry_checker_tx);
+
+    tokio::spawn(listing_expiry_checker_task::task(
+        Box::new(BotMessageSender::new(*bot.clone(), None)),
+        daos.clone(),
+        listing_expiry_checker_rx,
+    ));

    // Set up the bot's command menu
    setup_bot_commands(&bot).await?;

+    let handler_with_deps = dptree::entry()
+        .filter_map(
+            |bot: Box<Bot>, update: Update, daos: DAOs, bot_username: BotUsername| {
+                let target = update_into_message_target(update)?;
+                Some(App::new(
+                    Box::new(BotMessageSender::new(*bot, Some(target))),
+                    daos.clone(),
+                    bot_username.0,
+                ))
+            },
+        )
+        .chain(main_handler());
+
    let dialog_storage = SqliteStorage::new(db_pool.clone(), Json).await?;
+    let bot_username = bot
+        .get_me()
+        .await?
+        .username
+        .as_ref()
+        .ok_or(anyhow!("Bot username not found"))?
+        .clone();

-    // Create dispatcher with dialogue system
-    Dispatcher::builder(
-        bot,
-        dptree::entry()
-            .enter_dialogue::<Update, SqliteStorage<Json>, DialogueRootState>()
-            .branch(new_listing_handler())
-            .branch(my_listings_handler())
-            .branch(
-                Update::filter_message().branch(
-                    dptree::entry()
-                        .filter_command::<Command>()
-                        .branch(dptree::case![Command::Start].endpoint(handle_start))
-                        .branch(dptree::case![Command::Help].endpoint(handle_help))
-                        .branch(dptree::case![Command::MyBids].endpoint(handle_my_bids))
-                        .branch(dptree::case![Command::Settings].endpoint(handle_settings)),
-                ),
+    Dispatcher::builder(bot, handler_with_deps)
+        .dependencies(dptree::deps![
+            dialog_storage,
+            daos,
+            BotUsername(bot_username)
+        ])
+        .enable_ctrlc_handler()
+        .worker_queue_size(1)
+        .build()
+        .dispatch()
+        .await;
+
+    Ok(())
+}
+
+async fn unknown_message_handler(msg: Message) -> BotResult {
+    Err(BotError::UserVisibleError(format!(
+        "Unknown command: `{}`\n\n\
+        Try /help to see the list of commands.\
+        ",
+        msg.text().unwrap_or("")
+    )))
+}
+
+fn filter_forwarded_from_pawctioneer_bot(message: Message, me: Me) -> bool {
+    if let Some(bot) = message.via_bot {
+        if bot.id == me.user.id {
+            return true;
+        }
+    }
+    false
+}
+
+async fn handle_forwarded_from_pawctioneer_bot(user: PersistedUser) -> BotResult {
+    info!("Received forwarded message from Pawctioneer Bot from {user:?}, ignoring...");
+    Ok(())
+}
+
+#[cfg(test)]
+mod tests {
+
+    use mockall::predicate::{always, function};
+
+    use super::*;
+    use crate::message_sender::MockMessageSender;
+    use crate::test_utils::*;
+
+    #[tokio::test]
+    async fn test_main_handler() {
+        let mut message_sender = MockMessageSender::new();
+        message_sender
+            .expect_send_html_message()
+            .times(1)
+            .with(
+                function(|text: &String| text.contains("Available Commands:")),
+                always(),
            )
-            .branch(Update::filter_message().endpoint(unknown_message_handler)),
-    )
-    .dependencies(dptree::deps![db_pool, dialog_storage])
-    .enable_ctrlc_handler()
-    .worker_queue_size(1)
-    .build()
-    .dispatch()
-    .await;
+            .returning(|_, _| Ok(()));
+        let Deps { deps, .. } = create_deps().await;
+        let mut deps = with_message_sender(deps, message_sender).await;
+        deps.insert(create_tele_update("/help"));
+        let handler = main_handler();
+        dptree::type_check(handler.sig(), &deps, &[]);

-    Ok(())
-}
-
-async fn unknown_message_handler(bot: Bot, msg: Message) -> HandlerResult {
-    bot.send_message(
-        msg.chat.id,
-        format!(
-            "
-            Unknown command: `{}`\n\n\
-            Try /help to see the list of commands.\
-            ",
-            msg.text().unwrap_or("")
-        ),
-    )
-    .await?;
-    Ok(())
+        let result = handler.dispatch(deps).await;
+        assert!(matches!(result, ControlFlow::Break(Ok(()))), "{:?}", result);
+    }
 }
--- a/src/message/mod.rs
+++ b/src/message/mod.rs
@@ -0,0 +1,44 @@
+use crate::db::{bid::PersistedBid, listing::PersistedListing, user::PersistedUser};
+
+#[derive(Debug, Clone, PartialEq)]
+pub enum MessageType {
+    UserHasBeenOutbidForBuyer {
+        listing: PersistedListing,
+        buyer: PersistedUser,
+    },
+    BidHasBeenPlacedForSeller {
+        listing: PersistedListing,
+        buyer: PersistedUser,
+        seller: PersistedUser,
+        bid: PersistedBid,
+    },
+    BidHasBeenConfirmedForBuyer {
+        listing: PersistedListing,
+        bid: PersistedBid,
+    },
+    BidInvalidListingExpired {
+        listing: PersistedListing,
+        buyer: PersistedUser,
+    },
+    UserHasWonListingForSeller {
+        listing: PersistedListing,
+        seller: PersistedUser,
+        buyer: PersistedUser,
+        bid: PersistedBid,
+    },
+    UserHasWonListingForBuyer {
+        listing: PersistedListing,
+        buyer: PersistedUser,
+        seller: PersistedUser,
+        bid: PersistedBid,
+    },
+    UserHasLostListingForBuyer {
+        listing: PersistedListing,
+        buyer: PersistedUser,
+        seller: PersistedUser,
+    },
+    ListingExpiredWithNoWinnerForSeller {
+        listing: PersistedListing,
+        seller: PersistedUser,
+    },
+}
--- a/src/message_sender.rs
+++ b/src/message_sender.rs
@@ -0,0 +1,50 @@
+use crate::{message::MessageType, BotResult, MessageTarget};
+use async_trait::async_trait;
+use teloxide::types::{
+    CallbackQueryId, InlineKeyboardMarkup, InlineQueryId, InlineQueryResult, Me,
+};
+
+#[async_trait]
+pub trait MessageSender {
+    async fn send_html_message(
+        &self,
+        text: String,
+        keyboard: Option<InlineKeyboardMarkup>,
+    ) -> BotResult;
+    fn with_target(&self, target: MessageTarget) -> BoxedMessageSender;
+    async fn answer_inline_query(
+        &self,
+        inline_query_id: InlineQueryId,
+        results: Vec<InlineQueryResult>,
+    ) -> BotResult;
+    async fn answer_callback_query(&self, query_id: CallbackQueryId) -> BotResult;
+    async fn get_me(&self) -> BotResult<Me>;
+    async fn send_message(&self, message: MessageType) -> BotResult;
+}
+
+pub type BoxedMessageSender = Box<dyn MessageSender + Send + Sync>;
+
+#[cfg(test)]
+mockall::mock! {
+    pub MessageSender {}
+    impl Clone for MessageSender {
+        fn clone(&self) -> Self;
+    }
+    #[async_trait]
+    impl MessageSender for MessageSender {
+        fn with_target(&self, target: MessageTarget) -> BoxedMessageSender;
+        async fn send_html_message(
+            &self,
+            text: String,
+            keyboard: Option<InlineKeyboardMarkup>,
+        ) -> BotResult;
+        async fn answer_inline_query(
+            &self,
+            inline_query_id: InlineQueryId,
+            results: Vec<InlineQueryResult>,
+        ) -> BotResult;
+        async fn answer_callback_query(&self, query_id: CallbackQueryId) -> BotResult;
+        async fn get_me(&self) -> BotResult<Me>;
+        async fn send_message(&self, message: MessageType) -> BotResult;
+    }
+}
--- a/src/message_target.rs
+++ b/src/message_target.rs
@@ -0,0 +1,84 @@
+use std::fmt::Debug;
+
+use teloxide::types::*;
+
+use crate::db::user::DbUser;
+
+#[derive(Debug, Clone)]
+pub struct MessageTarget {
+    pub chat_id: ChatId,
+    pub message_id: Option<MessageId>,
+}
+
+impl MessageTarget {
+    pub fn only_chat_id(self) -> MessageTarget {
+        MessageTarget {
+            chat_id: self.chat_id,
+            message_id: None,
+        }
+    }
+}
+
+impl From<ChatId> for MessageTarget {
+    fn from(val: ChatId) -> Self {
+        MessageTarget {
+            chat_id: val,
+            message_id: None,
+        }
+    }
+}
+
+impl From<Chat> for MessageTarget {
+    fn from(val: Chat) -> Self {
+        MessageTarget {
+            chat_id: val.id,
+            message_id: None,
+        }
+    }
+}
+
+impl From<User> for MessageTarget {
+    fn from(val: User) -> Self {
+        MessageTarget {
+            chat_id: val.id.into(),
+            message_id: None,
+        }
+    }
+}
+
+impl From<(User, MessageId)> for MessageTarget {
+    fn from(val: (User, MessageId)) -> Self {
+        MessageTarget {
+            chat_id: val.0.id.into(),
+            message_id: Some(val.1),
+        }
+    }
+}
+
+impl From<(Chat, MessageId)> for MessageTarget {
+    fn from(val: (Chat, MessageId)) -> Self {
+        MessageTarget {
+            chat_id: val.0.id,
+            message_id: Some(val.1),
+        }
+    }
+}
+
+impl<P: Debug + Clone> From<DbUser<P>> for MessageTarget {
+    fn from(val: DbUser<P>) -> Self {
+        MessageTarget {
+            chat_id: val.telegram_id.into(),
+            message_id: None,
+        }
+    }
+}
+
+impl TryFrom<&CallbackQuery> for MessageTarget {
+    type Error = ();
+    fn try_from(val: &CallbackQuery) -> Result<Self, Self::Error> {
+        Ok(MessageTarget {
+            chat_id: val.from.id.into(),
+            message_id: val.message.as_ref().map(MaybeInaccessibleMessage::id),
+        })
+    }
+}
--- a/src/message_utils.rs
+++ b/src/message_utils.rs
@@ -1,138 +1,11 @@
-use crate::HandlerResult;
-use anyhow::bail;
+use crate::{db::user::PersistedUser, message_sender::BoxedMessageSender, BotResult};
+use anyhow::anyhow;
+use chrono::{DateTime, Utc};
 use num::One;
 use std::fmt::Display;
-use teloxide::{
-    payloads::{EditMessageTextSetters as _, SendMessageSetters as _},
-    prelude::Requester as _,
-    types::{
-        CallbackQuery, Chat, ChatId, InlineKeyboardButton, InlineKeyboardMarkup, MessageId,
-        ParseMode, User,
-    },
-    Bot,
-};
-
-#[derive(Debug, Clone, Copy)]
-pub struct HandleAndId<'s> {
-    pub handle: Option<&'s str>,
-    pub id: ChatId,
-}
-impl<'s> Display for HandleAndId<'s> {
-    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-        write!(f, "{}", self.handle.unwrap_or("unknown"))?;
-        write!(f, " ({})", self.id.0)?;
-        Ok(())
-    }
-}
-impl<'s> HandleAndId<'s> {
-    pub fn from_chat(chat: &'s Chat) -> Self {
-        Self {
-            handle: chat.username(),
-            id: chat.id,
-        }
-    }
-    pub fn from_user(user: &'s User) -> Self {
-        Self {
-            handle: user.username.as_deref(),
-            id: user.id.into(),
-        }
-    }
-}
-
-impl<'s> From<&'s User> for HandleAndId<'s> {
-    fn from(val: &'s User) -> Self {
-        HandleAndId::from_user(val)
-    }
-}
-impl<'s> From<&'s Chat> for HandleAndId<'s> {
-    fn from(val: &'s Chat) -> Self {
-        HandleAndId::from_chat(val)
-    }
-}
-
-pub fn is_cancel(text: &str) -> bool {
-    text.eq_ignore_ascii_case("/cancel")
-}
-
-#[derive(Debug, Clone)]
-pub struct MessageTarget {
-    pub chat_id: ChatId,
-    pub message_id: Option<MessageId>,
-}
-
-impl From<ChatId> for MessageTarget {
-    fn from(val: ChatId) -> Self {
-        MessageTarget {
-            chat_id: val,
-            message_id: None,
-        }
-    }
-}
-
-impl From<Chat> for MessageTarget {
-    fn from(val: Chat) -> Self {
-        MessageTarget {
-            chat_id: val.id,
-            message_id: None,
-        }
-    }
-}
-
-impl From<User> for MessageTarget {
-    fn from(val: User) -> Self {
-        MessageTarget {
-            chat_id: val.id.into(),
-            message_id: None,
-        }
-    }
-}
-
-impl From<(User, MessageId)> for MessageTarget {
-    fn from(val: (User, MessageId)) -> Self {
-        MessageTarget {
-            chat_id: val.0.id.into(),
-            message_id: Some(val.1),
-        }
-    }
-}
-
-impl From<(Chat, MessageId)> for MessageTarget {
-    fn from(val: (Chat, MessageId)) -> Self {
-        MessageTarget {
-            chat_id: val.0.id,
-            message_id: Some(val.1),
-        }
-    }
-}
-
-// Unified HTML message sending utility
-pub async fn send_message(
-    bot: &Bot,
-    message_target: impl Into<MessageTarget>,
-    text: impl AsRef<str>,
-    keyboard: Option<InlineKeyboardMarkup>,
-) -> HandlerResult {
-    let message_target = message_target.into();
-    if let Some(message_id) = message_target.message_id {
-        let mut message = bot
-            .edit_message_text(message_target.chat_id, message_id, text.as_ref())
-            .parse_mode(ParseMode::Html);
-        if let Some(kb) = keyboard {
-            message = message.reply_markup(kb);
-        }
-        message.await?;
-    } else {
-        let mut message = bot
-            .send_message(message_target.chat_id, text.as_ref())
-            .parse_mode(ParseMode::Html);
-        if let Some(kb) = keyboard {
-            message = message.reply_markup(kb);
-        }
-        message.await?;
-    }
-    Ok(())
-}
+use teloxide::types::{CallbackQuery, InlineKeyboardButton, InlineKeyboardMarkup};

+//
 // ============================================================================
 // KEYBOARD CREATION UTILITIES
 // ============================================================================
@@ -142,44 +15,14 @@ pub fn create_single_button_keyboard(text: &str, callback_data: &str) -> InlineK
    InlineKeyboardMarkup::new([[InlineKeyboardButton::callback(text, callback_data)]])
 }

-// Create a keyboard with multiple buttons in a single row
-pub fn create_single_row_keyboard(buttons: &[(&str, &str)]) -> InlineKeyboardMarkup {
-    let keyboard_buttons: Vec<InlineKeyboardButton> = buttons
-        .iter()
-        .map(|(text, callback_data)| InlineKeyboardButton::callback(*text, *callback_data))
-        .collect();
-    InlineKeyboardMarkup::new([keyboard_buttons])
-}
-
-// Create a keyboard with multiple rows
-pub fn create_multi_row_keyboard(rows: &[&[(&str, &str)]]) -> InlineKeyboardMarkup {
-    let mut keyboard = InlineKeyboardMarkup::default();
-    for row in rows {
-        let buttons: Vec<InlineKeyboardButton> = row
-            .iter()
-            .map(|(text, callback_data)| InlineKeyboardButton::callback(*text, *callback_data))
-            .collect();
-        keyboard = keyboard.append_row(buttons);
-    }
-    keyboard
-}
-
 // Extract callback data and answer callback query
 pub async fn extract_callback_data(
-    bot: &Bot,
+    bot: &BoxedMessageSender,
    callback_query: CallbackQuery,
-) -> HandlerResult<(String, User, MessageId)> {
+) -> BotResult<String> {
    let data = match callback_query.data {
        Some(data) => data,
-        None => bail!("Missing data in callback query"),
-    };
-
-    let from = callback_query.from.clone();
-
-    let message_id = if let Some(m) = callback_query.message {
-        m.id()
-    } else {
-        bail!("Missing message in callback query")
+        None => return Err(anyhow!("Missing data in callback query"))?,
    };

    // Answer the callback query to remove loading state
@@ -187,7 +30,7 @@ pub async fn extract_callback_data(
        log::warn!("Failed to answer callback query: {e}");
    }

-    Ok((data, from, message_id))
+    Ok(data)
 }

 pub fn pluralize<'a, N: One + PartialEq<N>>(
@@ -209,3 +52,21 @@ pub fn pluralize_with_count<N: One + PartialEq<N> + Display + Copy>(
 ) -> String {
    format!("{} {}", count, pluralize(count, singular, plural))
 }
+
+pub fn format_datetime(dt: DateTime<Utc>) -> String {
+    dt.format("%b %d, %Y %H:%M UTC").to_string()
+}
+
+pub fn user_name_or_link(user: &PersistedUser) -> String {
+    let link = format!("tg://user?id={}", user.telegram_id);
+    let name = if let Some(last_name) = &user.last_name {
+        format!("{} {}", user.first_name, last_name)
+    } else {
+        user.first_name.clone()
+    };
+    if let Some(username) = &user.username {
+        format!("<a href='{link}'>@{username} ({name})</a>")
+    } else {
+        format!("<a href='{link}'>{name}</a>")
+    }
+}
--- a/src/start_command_data.rs
+++ b/src/start_command_data.rs
@@ -0,0 +1,195 @@
+use base64::{prelude::BASE64_URL_SAFE, Engine};
+use teloxide::types::{CallbackQuery, MediaKind, MessageKind, UpdateKind};
+
+use crate::db::DbListingId;
+
+#[derive(Debug, Clone, PartialEq, Eq, Copy)]
+pub enum StartCommandData {
+    PlaceBidOnListing(DbListingId),
+    ViewListingDetailsAsBuyer(DbListingId),
+    ViewListingBids(DbListingId),
+}
+
+const PLACE_BID_ON_LISTING: &str = "place_bid_on_listing";
+const VIEW_LISTING_DETAILS_AS_BUYER: &str = "view_listing_details_as_buyer";
+const VIEW_LISTING_BIDS: &str = "view_listing_bids";
+
+impl From<StartCommandData> for String {
+    fn from(value: StartCommandData) -> Self {
+        match value {
+            StartCommandData::PlaceBidOnListing(listing_id) => {
+                format!("{PLACE_BID_ON_LISTING}:{listing_id}")
+            }
+            StartCommandData::ViewListingDetailsAsBuyer(listing_id) => {
+                format!("{VIEW_LISTING_DETAILS_AS_BUYER}:{listing_id}")
+            }
+            StartCommandData::ViewListingBids(listing_id) => {
+                format!("{VIEW_LISTING_BIDS}:{listing_id}")
+            }
+        }
+    }
+}
+
+#[derive(Debug, PartialEq, Eq, Clone)]
+pub enum StartCommandDataError {
+    MissingCommandName,
+    UnknownCommandName(String),
+    InvalidIdPart(String),
+    MissingIdPart,
+}
+
+impl TryFrom<String> for StartCommandData {
+    type Error = StartCommandDataError;
+    fn try_from(value: String) -> Result<Self, Self::Error> {
+        Self::try_from(value.as_str())
+    }
+}
+
+impl TryFrom<&String> for StartCommandData {
+    type Error = StartCommandDataError;
+    fn try_from(value: &String) -> Result<Self, Self::Error> {
+        Self::try_from(value.as_str())
+    }
+}
+
+impl TryFrom<&str> for StartCommandData {
+    type Error = StartCommandDataError;
+    fn try_from(value: &str) -> Result<Self, Self::Error> {
+        let mut parts = value.split(":").map(|s| s.trim());
+        let name = parts
+            .next()
+            .ok_or(StartCommandDataError::MissingCommandName)?;
+
+        let mut get_id_part = || -> Result<i64, StartCommandDataError> {
+            let id_part = parts.next().ok_or(StartCommandDataError::MissingIdPart)?;
+            id_part.parse::<i64>().map_err(|_| {
+                if id_part.is_empty() {
+                    StartCommandDataError::MissingIdPart
+                } else {
+                    StartCommandDataError::InvalidIdPart(id_part.to_string())
+                }
+            })
+        };
+
+        Ok(match name {
+            "" => return Err(StartCommandDataError::MissingCommandName),
+            PLACE_BID_ON_LISTING => Self::PlaceBidOnListing(DbListingId::new(get_id_part()?)),
+            VIEW_LISTING_DETAILS_AS_BUYER => {
+                Self::ViewListingDetailsAsBuyer(DbListingId::new(get_id_part()?))
+            }
+            VIEW_LISTING_BIDS => Self::ViewListingBids(DbListingId::new(get_id_part()?)),
+            _ => return Err(StartCommandDataError::UnknownCommandName(name.to_string())),
+        })
+    }
+}
+
+impl StartCommandData {
+    pub fn get_from_update(update: teloxide::types::Update) -> Option<StartCommandData> {
+        let message = match update.kind {
+            UpdateKind::Message(message) => Some(message),
+            _ => None,
+        }?;
+        let message = match message.kind {
+            MessageKind::Common(message) => Some(message),
+            _ => None,
+        }?;
+        let message = match message.media_kind {
+            MediaKind::Text(media_text) => Some(media_text),
+            _ => None,
+        }?;
+        let message = message.text.strip_prefix("/start ")?;
+        let decoded = BASE64_URL_SAFE.decode(message).ok()?;
+        let decoded = String::from_utf8(decoded).ok()?;
+        StartCommandData::try_from(decoded.as_str()).ok()
+    }
+
+    pub fn get_from_callback_query(callback_query: CallbackQuery) -> Option<StartCommandData> {
+        let data = callback_query.data.as_ref()?;
+        StartCommandData::try_from(data.as_str()).ok()
+    }
+
+    pub fn encode_for_start_command(self) -> String {
+        let as_string: String = self.into();
+        BASE64_URL_SAFE.encode(as_string)
+    }
+
+    pub fn get_place_bid_on_listing_start_command(
+        command: StartCommandData,
+    ) -> Option<DbListingId> {
+        if let StartCommandData::PlaceBidOnListing(listing_id) = command {
+            Some(listing_id)
+        } else {
+            None
+        }
+    }
+
+    pub fn get_view_listing_details_as_buyer_start_command(
+        command: StartCommandData,
+    ) -> Option<DbListingId> {
+        if let StartCommandData::ViewListingDetailsAsBuyer(listing_id) = command {
+            Some(listing_id)
+        } else {
+            None
+        }
+    }
+
+    pub fn get_view_listing_bids_start_command(command: StartCommandData) -> Option<DbListingId> {
+        if let StartCommandData::ViewListingBids(listing_id) = command {
+            Some(listing_id)
+        } else {
+            None
+        }
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use rstest::rstest;
+
+    use crate::{
+        db::DbListingId,
+        start_command_data::{StartCommandData, StartCommandDataError},
+        test_utils::create_tele_update,
+    };
+
+    #[test]
+    fn test_get_from_update() {
+        let update = create_tele_update("/start cGxhY2VfYmlkX29uX2xpc3Rpbmc6Mg==");
+        let command = StartCommandData::get_from_update(update);
+        assert_eq!(
+            command,
+            Some(StartCommandData::PlaceBidOnListing(DbListingId::new(2)))
+        );
+    }
+
+    #[test]
+    fn test_malformed_from_update() {
+        let update = create_tele_update("/start cGxhY2VfYmlkX29uX2xpc3Rpbmc6Mg");
+        let command = StartCommandData::get_from_update(update);
+        assert_eq!(command, None);
+    }
+
+    #[rstest]
+    #[case(StartCommandData::PlaceBidOnListing(DbListingId::new(1)))]
+    #[case(StartCommandData::ViewListingDetailsAsBuyer(DbListingId::new(2)))]
+    #[case(StartCommandData::ViewListingBids(DbListingId::new(3)))]
+    fn test_start_command_data(#[case] command: StartCommandData) {
+        let encoded: String = command.into();
+        let decoded = StartCommandData::try_from(encoded).unwrap();
+        assert_eq!(command, decoded);
+    }
+
+    #[rstest]
+    #[case("", StartCommandDataError::MissingCommandName)]
+    #[case("malformed", StartCommandDataError::UnknownCommandName("malformed".to_string()))]
+    #[case("place_bid_on_listing", StartCommandDataError::MissingIdPart)]
+    #[case("place_bid_on_listing:", StartCommandDataError::MissingIdPart)]
+    #[case("place_bid_on_listing:abc", StartCommandDataError::InvalidIdPart("abc".to_string()))]
+    fn test_malformed_start_command_data(
+        #[case] encoded: &str,
+        #[case] expected_error: StartCommandDataError,
+    ) {
+        let decoded = StartCommandData::try_from(encoded);
+        assert_eq!(decoded, Err(expected_error));
+    }
+}
--- a/src/test_utils.rs
+++ b/src/test_utils.rs
@@ -1,5 +1,29 @@
 //! Test utilities including timestamp comparison macros

+use chrono::{Duration, Utc};
+use dptree::di::DependencyMap;
+use sqlx::SqlitePool;
+use std::{ops::Deref, str::FromStr, sync::Arc};
+use teloxide::dispatching::dialogue::serializer::Json;
+use teloxide::types::*;
+use tokio::sync::mpsc::Receiver;
+
+use crate::{
+    db::{
+        listing::{
+            BasicAuctionFields, ListingBase,
+            ListingFields::{self, BasicAuction},
+            NewListing, PersistedListing,
+        },
+        user::{NewUser, PersistedUser},
+        CurrencyType, DAOs, ListingDAO, ListingEventSender, ListingUpdatedEvent, MoneyAmount,
+        UserDAO,
+    },
+    message_sender::MockMessageSender,
+    sqlite_storage::SqliteStorage,
+    App, DialogueRootState, RootDialogue,
+};
+
 /// Assert that two timestamps are approximately equal within a given epsilon tolerance.
 ///
 /// This macro is useful for testing timestamps that may have small variations due to
@@ -87,54 +111,210 @@ macro_rules! assert_timestamps_approx_eq_default {
    };
 }

-/// Assert that the `starts_at` and `ends_at` fields of two structs are approximately equal.
-///
-/// This macro is specifically designed for comparing listing timestamps where small
-/// variations in timing are expected. Uses a default epsilon of 1 second.
-///
-/// # Examples
-///
-/// ```
-/// use chrono::Utc;
-/// use crate::test_utils::assert_listing_timestamps_approx_eq;
-///
-/// let original_listing = /* some listing */;
-/// let reconstructed_listing = /* reconstructed from DB */;
-///
-/// // Compare both starts_at and ends_at with default 1s epsilon
-/// assert_listing_timestamps_approx_eq!(
-///     original_listing.base,
-///     reconstructed_listing.base
-/// );
-/// ```
-#[macro_export]
-macro_rules! assert_listing_timestamps_approx_eq {
-    ($left:expr, $right:expr) => {
-        $crate::assert_timestamps_approx_eq_default!(
-            $left.starts_at,
-            $right.starts_at,
-            "starts_at timestamps don't match"
-        );
-        $crate::assert_timestamps_approx_eq_default!(
-            $left.ends_at,
-            $right.ends_at,
-            "ends_at timestamps don't match"
-        );
+pub async fn create_test_pool() -> SqlitePool {
+    let pool = SqlitePool::connect("sqlite::memory:")
+        .await
+        .expect("Failed to create in-memory database");
+
+    // Run migrations
+    sqlx::migrate!("./migrations")
+        .run(&pool)
+        .await
+        .expect("Failed to run database migrations");
+
+    pool
+}
+
+pub fn create_tele_user(user_fn: impl FnOnce(&mut User) -> ()) -> User {
+    let mut user = User {
+        id: UserId(1),
+        username: Some("username".to_string()),
+        first_name: "firstname".to_string(),
+        last_name: Some("lastname".to_string()),
+        is_bot: false,
+        language_code: Some("en".to_string()),
+        is_premium: false,
+        added_to_attachment_menu: false,
    };
-    ($left:expr, $right:expr, $epsilon:expr) => {
-        $crate::assert_timestamps_approx_eq!(
-            $left.starts_at,
-            $right.starts_at,
-            $epsilon,
-            "starts_at timestamps don't match"
-        );
-        $crate::assert_timestamps_approx_eq!(
-            $left.ends_at,
-            $right.ends_at,
-            $epsilon,
-            "ends_at timestamps don't match"
-        );
+    user_fn(&mut user);
+    user
+}
+
+pub fn create_tele_private_chat(user: &User) -> Chat {
+    Chat {
+        id: ChatId(1),
+        kind: ChatKind::Private(ChatPrivate {
+            username: user.username.clone(),
+            first_name: Some(user.first_name.clone()),
+            last_name: user.last_name.clone(),
+        }),
+    }
+}
+
+pub fn create_tele_update(message_text: &str) -> Update {
+    let user = create_tele_user(|user| user.username = Some("sender".to_string()));
+    let chat = create_tele_private_chat(&user);
+    Update {
+        id: UpdateId(1),
+        kind: UpdateKind::Message(Message {
+            id: MessageId(1),
+            thread_id: None,
+            from: Some(user),
+            sender_chat: None,
+            date: Utc::now(),
+            chat,
+            is_topic_message: false,
+            via_bot: None,
+            sender_business_bot: None,
+            kind: MessageKind::Common(MessageCommon {
+                media_kind: MediaKind::Text(MediaText {
+                    text: message_text.to_string(),
+                    entities: vec![],
+                    link_preview_options: None,
+                }),
+                author_signature: None,
+                paid_star_count: None,
+                effect_id: None,
+                forward_origin: None,
+                reply_to_message: None,
+                external_reply: None,
+                quote: None,
+                reply_to_story: None,
+                sender_boost_count: None,
+                edit_date: None,
+                reply_markup: None,
+                is_automatic_forward: false,
+                has_protected_content: false,
+                is_from_offline: false,
+                business_connection_id: None,
+            }),
+        }),
+    }
+}
+
+pub fn create_tele_callback_query(callback_data: &str, from: User) -> CallbackQuery {
+    CallbackQuery {
+        id: CallbackQueryId("query_id".to_string()),
+        data: Some(callback_data.to_string()),
+        from: from.clone(),
+        message: None,
+        chat_instance: "chat_instance".to_string(),
+        inline_message_id: None,
+        game_short_name: None,
+    }
+}
+
+pub struct Deps {
+    pub deps: DependencyMap,
+    pub listing_event_receiver: Receiver<ListingUpdatedEvent>,
+}
+pub async fn create_deps() -> Deps {
+    let pool = create_test_pool().await;
+    let dialog_storage = SqliteStorage::new(pool.clone(), Json).await.unwrap();
+    let (tx, rx) = ListingEventSender::channel();
+    let daos = DAOs::new(pool, tx);
+    let me_user = create_tele_user(|user| user.username = Some("me".to_string()));
+    let me = Me {
+        user: me_user,
+        can_join_groups: true,
+        can_read_all_group_messages: true,
+        supports_inline_queries: true,
+        can_connect_to_business: true,
+        has_main_web_app: true,
    };
+    Deps {
+        deps: dptree::deps![dialog_storage, me, daos],
+        listing_event_receiver: rx,
+    }
+}
+
+pub async fn with_dialogue(mut deps: DependencyMap, user: &PersistedUser) -> DependencyMap {
+    let storage = deps.get::<Arc<SqliteStorage<Json>>>().deref().clone();
+    let dialogue = RootDialogue::new(storage, user.telegram_id.into());
+    dialogue.update(DialogueRootState::Start).await.unwrap();
+    deps.insert(dialogue);
+    deps
+}
+
+pub async fn with_message_sender(
+    mut deps: DependencyMap,
+    mock_bot: MockMessageSender,
+) -> DependencyMap {
+    let app = App::new(
+        Box::new(mock_bot),
+        deps.get::<DAOs>().deref().clone(),
+        "bot_username".to_string(),
+    );
+    deps.insert(app);
+    deps
+}
+
+pub async fn with_test_user(
+    deps: &DependencyMap,
+    user_fn: impl FnOnce(&mut NewUser) -> (),
+) -> PersistedUser {
+    let user_dao = deps.get::<DAOs>().user.clone();
+    let mut new_user = NewUser {
+        persisted: (),
+        telegram_id: 12345.into(),
+        first_name: "Test User".to_string(),
+        last_name: None,
+        username: Some("testuser".to_string()),
+        is_banned: false,
+    };
+    user_fn(&mut new_user);
+    user_dao.insert_user(&new_user).await.unwrap()
+}
+
+pub async fn with_test_listing(
+    deps: &DependencyMap,
+    seller: &PersistedUser,
+    listing_fn: impl FnOnce(&mut NewListing) -> (),
+) -> PersistedListing {
+    let listing_dao = deps.get::<DAOs>().listing.clone();
+    let mut new_listing = NewListing {
+        persisted: (),
+        base: ListingBase {
+            seller_id: seller.persisted.id,
+            title: "Test Listing".to_string(),
+            description: Some("Test description".to_string()),
+            starts_at: Utc::now(),
+            ends_at: Utc::now() + Duration::days(3),
+            currency_type: CurrencyType::Usd,
+            is_active: true,
+        },
+        fields: ListingFields::BasicAuction(BasicAuctionFields {
+            starting_bid: MoneyAmount::from_str("100.00").unwrap(),
+            buy_now_price: Some(MoneyAmount::from_str("100.00").unwrap()),
+            min_increment: MoneyAmount::from_str("1.00").unwrap(),
+            anti_snipe_minutes: Some(5),
+        }),
+    };
+    listing_fn(&mut new_listing);
+    listing_dao.insert_listing(&new_listing).await.unwrap()
+}
+
+pub async fn create_test_listing(dao: &ListingDAO, seller: &PersistedUser) -> PersistedListing {
+    dao.insert_listing(&NewListing {
+        persisted: (),
+        base: ListingBase {
+            seller_id: seller.persisted.id,
+            title: "Test Listing".to_string(),
+            description: Some("Test description".to_string()),
+            starts_at: Utc::now(),
+            ends_at: Utc::now() + Duration::days(3),
+            currency_type: CurrencyType::Usd,
+            is_active: true,
+        },
+        fields: BasicAuction(BasicAuctionFields {
+            starting_bid: MoneyAmount::from_str("100.00").unwrap(),
+            buy_now_price: Some(MoneyAmount::from_str("100.00").unwrap()),
+            min_increment: MoneyAmount::from_str("1.00").unwrap(),
+            anti_snipe_minutes: Some(5),
+        }),
+    })
+    .await
+    .unwrap()
 }

 #[cfg(test)]
--- a/src/wrap_endpoint.rs
+++ b/src/wrap_endpoint.rs
@@ -0,0 +1,141 @@
+use dptree::di::{CompiledFn, DependencyMap, Injectable};
+use dptree::Type;
+use std::sync::Arc;
+use std::{collections::BTreeSet, future::Future, marker::PhantomData};
+
+pub struct WrappedAsyncFn<FnBase, FnError, ErrorType, FnBaseArgs, FnErrorArgs> {
+    fn_base: FnBase,
+    fn_error: FnError,
+    _error_type: PhantomData<ErrorType>,
+    _fn_base_args: PhantomData<FnBaseArgs>,
+    _fn_error_args: PhantomData<FnErrorArgs>,
+}
+
+impl<FnBase, FnError, ErrorType, FnBaseArgs, FnErrorArgs>
+    WrappedAsyncFn<FnBase, FnError, ErrorType, FnBaseArgs, FnErrorArgs>
+{
+    fn new(fn_base: FnBase, fn_error: FnError) -> Self {
+        Self {
+            fn_base,
+            fn_error,
+            _error_type: PhantomData,
+            _fn_base_args: PhantomData,
+            _fn_error_args: PhantomData,
+        }
+    }
+}
+
+macro_rules! generate_wrapped {
+    ([$($base_generic:ident),*], [$($error_generic:ident),*]) => {
+        impl<FnBase, FnError, FnBaseFut, FnErrorFut, T, ErrorType, $($base_generic,)* $($error_generic,)*>
+            Injectable<Result<T, ErrorType>, ($($base_generic,)* $($error_generic,)*)>
+            for WrappedAsyncFn<FnBase, FnError, ErrorType, ($($base_generic,)*), ($($error_generic,)*)>
+        where
+            FnBase: Fn($($base_generic,)*) -> FnBaseFut + Send + Sync + 'static,
+            FnBaseFut: Future<Output = Result<T, ErrorType>> + Send + 'static,
+            FnError: Fn($($error_generic,)* ErrorType) -> FnErrorFut + Send + Sync + 'static,
+            FnErrorFut: Future<Output = Result<T, ErrorType>> + Send + 'static,
+            T: 'static + Send + Sync,
+            ErrorType: 'static + Send + Sync,
+            $($base_generic: Clone + Send + Sync + 'static,)*
+            $($error_generic: Clone + Send + Sync + 'static,)*
+        {
+            #[allow(non_snake_case)]
+            #[allow(unused_variables)]
+            fn inject<'a>(&'a self, container: &'a DependencyMap) -> CompiledFn<'a, Result<T, ErrorType>> {
+                Arc::new(move || {
+                    $(let $base_generic = std::borrow::Borrow::<$base_generic>::borrow(&container.get()).clone();)*
+                    let base_fut = (self.fn_base)($($base_generic),*);
+                    Box::pin(async move {
+                        match base_fut.await {
+                            Ok(t) => Ok(t),
+                            Err(err) => {
+                                $(let $error_generic = std::borrow::Borrow::<$error_generic>::borrow(&container.get()).clone();)*
+                                (self.fn_error)($($error_generic,)* err).await
+                            }
+                        }
+                    })
+                })
+            }
+
+            fn input_types() -> BTreeSet<Type> {
+                BTreeSet::from_iter(vec![
+                    $(Type::of::<$base_generic>(),)*
+                    $(Type::of::<$error_generic>(),)*
+                ])
+            }
+        }
+    };
+}
+
+macro_rules! generate_wrapped_all {
+    // Entry: two lists (base generics, error generics)
+    ([$($base:ident),*], [$($err:ident),*]) => {
+        generate_wrapped_all!(@recurse_base [$($base),*] [$($err),*]);
+    };
+
+    // Recurse over base prefixes (from full list down to empty)
+    (@recurse_base [] [$($err:ident),*]) => {
+        generate_wrapped_all!(@recurse_err [] [$($err),*]);
+    };
+    (@recurse_base [$head:ident $(, $tail:ident)*] [$($err:ident),*]) => {
+        generate_wrapped_all!(@recurse_err [$head $(, $tail)*] [$($err),*]);
+        generate_wrapped_all!(@recurse_base [$( $tail ),*] [$($err),*]);
+    };
+
+    // For a fixed base prefix, recurse over error prefixes (from full list down to empty)
+    (@recurse_err [$($base_current:ident),*] []) => {
+        generate_wrapped!([$($base_current),*], []);
+    };
+    (@recurse_err [$($base_current:ident),*] [$ehead:ident $(, $etail:ident)*]) => {
+        generate_wrapped!([$($base_current),*], [$ehead $(, $etail)*]);
+        generate_wrapped_all!(@recurse_err [$($base_current),*] [$( $etail ),*]);
+    };
+}
+
+// Generate cartesian product of prefixes up to 12 base generics and 2 error generics
+generate_wrapped_all!(
+    [T1, T2, T3, T4, T5, T6, T7, T8, T9, T10, T11, T12],
+    [E1, E2]
+);
+
+pub fn wrap_endpoint<FnBase, FnError, ErrorType, FnBaseArgs, FnErrorArgs>(
+    fn_base: FnBase,
+    error_fn: FnError,
+) -> WrappedAsyncFn<FnBase, FnError, ErrorType, FnBaseArgs, FnErrorArgs> {
+    WrappedAsyncFn::new(fn_base, error_fn)
+}
+
+#[cfg(test)]
+mod tests {
+    use crate::wrap_endpoint;
+    use dptree::{deps, Handler};
+    use std::ops::ControlFlow;
+    use teloxide::dispatching::DpHandlerDescription;
+
+    #[derive(Debug, PartialEq, Eq)]
+    enum MyError {
+        ErrorValue,
+    }
+    type MyHandler = Handler<'static, Result<&'static str, MyError>, DpHandlerDescription>;
+
+    #[tokio::test]
+    async fn test_handler_errors() {
+        let service: MyHandler = dptree::entry().endpoint(wrap_endpoint(
+            async |_: &'static str| Err(MyError::ErrorValue),
+            async |_: MyError| Ok("caught"),
+        ));
+        let result = service.dispatch(deps!["test"]).await;
+        assert_eq!(result, ControlFlow::Break(Ok("caught")));
+    }
+
+    #[tokio::test]
+    async fn test_handler_ok() {
+        let service: MyHandler = dptree::entry().endpoint(wrap_endpoint(
+            async |arg1: &'static str| Ok(arg1),
+            async |error: MyError| Err(error),
+        ));
+        let result = service.dispatch(deps!["test"]).await;
+        assert_eq!(result, ControlFlow::Break(Ok("test")));
+    }
+}
Author	SHA1	Message	Date
Dylan Knutson	4396d367a8	active listing constraint for bidding	2025-09-10 23:51:01 +00:00
Dylan Knutson	212a72c511	send messages to winners / losers of an auction	2025-09-10 03:53:48 +00:00
Dylan Knutson	a955acbdce	add listing expiry checker task	2025-09-10 03:15:58 +00:00
Dylan Knutson	7eada9588c	tests for bidding when auction is expired	2025-09-09 02:45:56 +00:00
Dylan Knutson	0d18016993	integration tests for confirm bid amount	2025-09-09 01:40:36 +00:00
Dylan Knutson	df137403a7	id renames	2025-09-05 22:48:17 +00:00
Dylan Knutson	1c7131d801	first integration test	2025-09-05 22:33:03 +00:00
Dylan Knutson	a40ac5f345	move target into state	2025-09-05 22:17:30 +00:00
Dylan Knutson	af5b8883af	mocakble message sender trait	2025-09-05 21:48:52 +00:00
Dylan Knutson	da7e59fe0f	create App struct	2025-09-05 03:50:09 +00:00
Dylan Knutson	9ad562a4b2	basic scaffold for placing bids	2025-09-03 00:28:46 +00:00
Dylan Knutson	c53dccbea2	error handler wrapper helper	2025-09-02 19:55:15 +00:00
Dylan Knutson	8610b4cc52	handler wrapper for catching error	2025-09-02 19:11:57 +00:00
Dylan Knutson	f74c3502d6	basic listing stuff	2025-09-02 01:47:45 +00:00
Dylan Knutson	da1fd1027f	more handler refactoring	2025-08-31 00:04:18 +00:00
Dylan Knutson	461ce3aba4	Update new_listing and my_listings functionality	2025-08-30 18:41:42 +00:00
Dylan Knutson	a39dd01452	Refactor bot commands and database models - Update my_listings command structure and keyboard handling - Enhance new_listing workflow with improved callbacks and handlers - Refactor database user model and keyboard utilities - Add new handler utilities module - Update main bot configuration and start command	2025-08-30 11:04:40 -07:00
Dylan Knutson	65a50b05e2	feat: Add inline keyboard support to auction listing inline queries - Add interactive inline keyboard with bid, watch, and share buttons - Implement separate inline query handler before dialogue system - Fix dispatcher structure to handle both inline queries and regular messages - Add dynamic bot username fetching for deep links - Support rich formatted auction listing messages with pricing info - Handle forward_listing:ID pattern for sharing specific auctions Resolves inline query handling and adds interactive auction sharing	2025-08-30 15:37:02 +00:00
Dylan Knutson	c9a824dd88	cargo clippy	2025-08-30 05:50:44 +00:00
Dylan Knutson	5d7a5b26c1	feat: enhance UX with listing type selection and main menu improvements - Add listing type selection to new listing wizard - Create SelectingListingType state for choosing between 4 listing types - Add ListingTypeKeyboardButtons with clear descriptions - Support BasicAuction, MultiSlotAuction, FixedPriceListing, BlindAuction - Update handlers to start with type selection before title input - Improve main menu navigation - Add main menu with action buttons for /start command - Create MainMenuButtons with New Listing, My Listings, My Bids, Settings, Help - Add back button to My Listings screen for better navigation - Implement proper dialogue state management between screens - Refactor callback handling for type safety - Convert string literal matching to enum-based callback handling - Use try_from() pattern for all keyboard button callbacks - Ensure compile-time safety and exhaustive matching - Apply pattern to listing type, slots, duration, and start time callbacks - Eliminate code duplication - Extract reusable main menu functions (enter_main_menu, get_main_menu_message) - Centralize main menu logic and message content - Update all main menu transitions to use shared functions - Technical improvements - Add proper error handling for invalid callback data - Maintain backward compatibility with existing flows - Follow established patterns for keyboard button definitions - Ensure all changes compile without errors	2025-08-30 05:45:49 +00:00
Dylan Knutson	9ef36b760e	feat: Add high-level integration testing framework - Created trait abstractions for dependency injection with mockall support - Added comprehensive integration tests focusing on: * Database operations and persistence * Complete user workflow scenarios * Dialogue state transitions and validation * Multi-user scenarios and data integrity - Removed trivial unit tests, kept only meaningful business logic tests - Added UserRepository, ListingRepository, and BotMessenger traits - Integration tests verify end-to-end workflows with real database - Total: 30 focused tests (4 unit + 8 integration + 18 validation tests) Key integration test scenarios: - Complete listing creation workflow with database persistence - Listing update workflows with state validation - Multi-user independent operations - Error handling that preserves data integrity - Business rule enforcement (e.g., no timing changes on live listings) Framework ready for advanced mock-based testing when needed.	2025-08-30 04:41:07 +00:00
Dylan Knutson	5fe4a52c2b	refactor: Split new_listing module into logical submodules - Organized 810-line monolithic file into 10 focused modules - Main mod.rs reduced from 810 to 27 lines (96.7% reduction) - Clear separation of concerns with logical hierarchy: Module Structure: ├── mod.rs (27 lines) - Module coordinator and exports ├── handlers.rs (362 lines) - Main teloxide handler functions ├── callbacks.rs (205 lines) - Callback query processing ├── validations.rs (145 lines) - Input validation logic ├── ui.rs (102 lines) - Display and summary functions ├── types.rs (82 lines) - Data structures and states ├── field_processing.rs (76 lines) - Core field update logic ├── messages.rs (73 lines) - Centralized message constants ├── handler_factory.rs (60 lines) - Teloxide handler tree └── keyboard.rs (55 lines) - Button and keyboard definitions Benefits: - Single responsibility principle enforced - Easy navigation and maintenance - Reduced coupling between components - Enhanced testability - All 112 tests still passing	2025-08-30 04:15:27 +00:00
Dylan Knutson	24819633f5	refactor: Aggressive refactoring of new_listing module - Reduced code size by 26.7% (1083→810 lines) - Eliminated ALL duplication patterns: * Consolidated 12 individual handlers into 2 unified handlers * Centralized all step messages and success messages into constants * Removed repetitive pattern matching and state transitions - Major architectural improvements: * Refactored ListingFields enum to use struct-based variants * Enhanced type safety with dedicated field structs * Simplified field access patterns throughout codebase - Updated database layer for new enum structure - Maintained full teloxide compatibility and functionality - All 112 tests still passing	2025-08-30 03:07:31 +00:00
Dylan Knutson	143bf3ce41	refactor: Update listing confirmation flow and summary display - Consolidate Create and Save button handling in confirmation flow - Add unsaved changes indicator to listing summary - Improve edit flow by using enter_edit_listing_draft function - Update confirmation button logic and user feedback messages - Clean up dialogue state management in confirmation handlers	2025-08-30 01:29:29 +00:00
Dylan Knutson	8fb51d12a7	feat: Add natural language duration parsing to validate_duration - Support parsing strings like '1 hour', '7 days' in addition to plain numbers - Maintain backwards compatibility with numeric input (e.g., '24') - Support units: hour(s), hr(s), day(s) - Add comprehensive test suite using rstest - Enforce 1-720 hour limit (1 hour to 30 days) - Provide clear error messages for invalid input	2025-08-30 00:17:24 +00:00
Dylan Knutson	374abf8c42	major db refactors	2025-08-29 23:25:12 +00:00