diff --git a/.env.example b/.env.example
index 2016955..670640c 100644
--- a/.env.example
+++ b/.env.example
@@ -13,6 +13,15 @@
 # Telegram chat ID for moderation messages. Required if bot token is set.
 # BOOK_TELEGRAM_CHAT_ID=0
 
+# Seconds between retry attempts for failed Telegram notifications.
+# BOOK_TELEGRAM_RETRY_INTERVAL=20
+
+# Maximum number of retry attempts for failed Telegram notifications.
+# BOOK_TELEGRAM_RETRY_LIMIT=3
+
+# Seconds between pending entry reminders. Set to 0 to disable.
+# BOOK_TELEGRAM_REMINDER_INTERVAL=86400
+
 # Enable honeypot field for spam prevention.
 # BOOK_ENABLE_HONEYPOT=true
 
diff --git a/README.md b/README.md
index 6552ad0..cee5552 100644
--- a/README.md
+++ b/README.md
@@ -104,6 +104,15 @@ Running `guestbook` with no env vars will give you a working guestbook on `local
 # Telegram chat ID for moderation messages. Required if bot token is set.
 # BOOK_TELEGRAM_CHAT_ID=0
 
+# Seconds between retry attempts for failed Telegram notifications.
+# BOOK_TELEGRAM_RETRY_INTERVAL=20
+
+# Maximum number of retry attempts for failed Telegram notifications.
+# BOOK_TELEGRAM_RETRY_LIMIT=3
+
+# Seconds between pending entry reminders. Set to 0 to disable.
+# BOOK_TELEGRAM_REMINDER_INTERVAL=86400
+
 # Enable honeypot field for spam prevention.
 # BOOK_ENABLE_HONEYPOT=true
 
@@ -142,16 +151,13 @@ Running `guestbook` with no env vars will give you a working guestbook on `local
 # Maximum length for website URLs. 0 for unlimited.
 # BOOK_MAX_WEBSITE_LENGTH=0
 
-# Separator between guestbook entries.
-# BOOK_SEPARATOR=------------------------------------------------------------
-
 # Path to a CSS file. Takes precedence over BOOK_STYLE. Uses built-in default if unset.
 # BOOK_STYLE_FILE=./templates/default.css
 
 # Custom CSS injected into a style tag.
 # Classes: .guestbook-form, .guestbook-prompt, .guestbook-label, .guestbook-input,
-#          .guestbook-textarea, .guestbook-button, .entry-header, .entry-date, .entry-name,
-#          .entry-website, .entry-body, .entry-separator
+#          .guestbook-textarea, .guestbook-button, .entry, .entry-header, .entry-date,
+#          .entry-name, .entry-website, .entry-body
 # BOOK_STYLE=
 
 # Text shown above the form.
@@ -239,6 +245,11 @@ services.guestbook = {
       enable = false;
       # botTokenFile = <path>;  -- required when enabled
       # chatId = <int>;         -- required when enabled
+      retry = {
+        interval = 20;
+        limit = 3;
+      };
+      reminderInterval = 86400;
     };
     security = {
       htmlInjection.enable = false;
@@ -264,7 +275,6 @@ services.guestbook = {
     cssFile = null;
     templateFile = null;
     successTemplateFile = null;
-    separator = "------------------------------------------------------------";
     greeting = "Thanks for visiting. Sign the guestbook!";
     labels = {
       submit = "sign";
@@ -288,7 +298,7 @@ Set `BOOK_ENABLE_DRAWINGS=true` to add a drawing canvas to the form. Visitors dr
 
 Server-side validation checks the PNG magic bytes (`\x89PNG\r\n\x1a\n`), then reads width/height from the IHDR chunk and rejects anything that doesn't match `BOOK_CANVAS_WIDTH` x `BOOK_CANVAS_HEIGHT`. Max file size is derived from canvas dimensions (`w * h * 4`, the raw RGBA ceiling). A 2MB request body limit is enforced on all form submissions.
 
-When Telegram moderation is enabled, drawings are sent as photos in the notification so you can see them before approving.
+When Telegram moderation is enabled, the notification includes a `/drawing_<id>` command to view the drawing on demand.
 
 ---
 
@@ -298,7 +308,7 @@ Set `BOOK_ENABLE_VOICE_NOTES=true` to let visitors record a short audio clip alo
 
 Server-side validation checks the WebM magic bytes (`\x1a\x45\xdf\xa3`) and enforces a file size cap derived from the max duration (`duration * 10KB`). Voice notes are stored as WebM files in `{data_dir}/voice_notes/` and rendered as native `<audio>` elements below the entry header, independent of the HTML injection setting.
 
-When Telegram moderation is enabled, voice notes are sent as voice messages in the notification so you can hear them before approving.
+When Telegram moderation is enabled, the notification includes a `/voice_note_<id>` command to listen on demand.
 
 ---
 
@@ -306,39 +316,62 @@ When Telegram moderation is enabled, voice notes are sent as voice messages in t
 
 To enable Telegram moderation, create a bot via [@BotFather](https://t.me/BotFather) and set `BOOK_TELEGRAM_BOT_TOKEN` to the token it gives you. Set `BOOK_TELEGRAM_CHAT_ID` to the chat ID where you want notifications sent: the easiest way to find this is to message the bot and check the [getUpdates](https://api.telegram.org/bot<token>/getUpdates) endpoint.
 
-When a visitor submits an entry, the bot sends a message with the entry details and `/allow_<id>` and `/deny_<id>` commands, as well as any drawing or voice note attached. Tap either command to approve or deny. Denying an entry offers a `/delete_<id>` command to remove it and its media from disk. If you approve something and later want to deny it, or vice versa, just hit the opposite option and it'll work as expected.
+When a visitor submits an entry, the bot sends a notification with the entry details and moderation commands. If the send fails, it retries in the background (`BOOK_TELEGRAM_RETRY_INTERVAL`, `BOOK_TELEGRAM_RETRY_LIMIT`). A periodic reminder will remind you about any pending entries once a day by default (`BOOK_TELEGRAM_REMINDER_INTERVAL` seconds, 0 to disable).
 
-The bot also registers these commands in the Telegram command menu (visible when you type `/`):
+#### Commands
 
-- `/pending` — list all pending entries with previews
-- `/approved` — list all approved entries
-- `/denied` — list all denied entries
+```bash
+# List pending, approved, or denied entries.
+/pending
+/approved
+/denied
 
-Each listed entry includes a `/view_<id>` link. Viewing an entry shows the full details, drawing, and voice note, along with `/allow_<id>` and `/deny_<id>` commands.
+# View the full details of an entry.
+/view_<id>
 
-To delete an entry and all its associated media (drawing, voice note), use `/delete_<id>`.
+# View entry attachments, if they exist.
+/drawing_<id>
+/voice_note_<id>
 
-None of these commands require clicking on the links. They'll all just work by typing them in the chat to your bot.
+# Approve and deny entries.
+/allow_<id>
+/deny_<id>
+
+# Append a reply to an entry.
+# Reply is a multi-line command. Your reply will be appended
+# to the guestbook entry, prefixed by `>>`.
+/reply_<id>
+[response]
+
+# Delete an entry.
+/delete_<id>
+/confirm_delete_<id>
+```
 
 ---
 
 ### Entry Format
 
-Each entry is a plain text file in `{data_dir}/entries/`. The filename is `{epoch}_{uuid}.txt`. If the entry has a drawing, the drawing is stored as `{epoch}_{uuid}.png` in `{data_dir}/drawings/` with the same prefix. Voice notes work the same way, stored as `{epoch}_{uuid}.webm` in `{data_dir}/voice_notes/`.
+Each entry is a plain text file in `{data_dir}/entries/`. The filename is a 4-character base36 ID (e.g., `ab3c.txt`). Drawings and voice notes share the same ID (`ab3c.png`, `ab3c.webm`) in their respective directories. Entries can be anchor linked via `#id`.
 
 ```
 +++
 name = "someone"
 date = "2026-04-09T12:00:00"
 website = "https://example.com"
-drawing = "1744185600_abcd1234.png"
-voice_note = "1744300800_abcd1234.webm"
-status = "pending"
+drawing = "ab3c.png"
+voice_note = "ab3c.webm"
+status = "approved"
 +++
-Message body here.
+Message body here. This is what someone
+entered into the 'message' field.
+
+>>  This is a reply. You can append
+>>  to a message manually, and format
+>>  yourself, or /reply_<id> to the bot.
 ```
 
-The `status` field can be `pending`, `approved`, or `denied`. Only approved entries are displayed. The `drawing` and `voice_note` fields are empty when there's no drawing or voice note. To moderate without Telegram, just edit the file and change `status` to `approved` or `denied`.
+`status` is either `pending`, `approved`, or `denied`. Only approved entries are displayed. `drawing` and `voice_note` fields link to their respective attachments, or nothing if they're empty. State is all stored in these files so you can moderate however you like, either via the built-in bot or just by manually editing the `status` field yourself.
 
 ---
 
@@ -363,8 +396,7 @@ The `status` field can be `pending`, `approved`, or `denied`. Only approved entr
               BOOK_LABEL_NAME, BOOK_LABEL_WEBSITE, BOOK_LABEL_MESSAGE,
               BOOK_BUTTON_TEXT, BOOK_TEXTAREA_WIDTH, BOOK_TEXTAREA_HEIGHT.
               Empty when BOOK_ENABLE_SUBMISSIONS=false.
-    entries - Approved guestbook entries, newest first. Entry separator
-              controlled by BOOK_SEPARATOR.
+    entries - Approved guestbook entries, newest first.
     style   - Custom CSS from BOOK_STYLE or BOOK_STYLE_FILE, wrapped in
               a <style> tag. Uses built-in default.css when neither is set.
 
@@ -381,8 +413,6 @@ The `status` field can be `pending`, `approved`, or `denied`. Only approved entr
 <body>
 <div class="page-container">
 {{title}}
-
-guestbook
 =========
 
 {{prompt}}
@@ -398,9 +428,35 @@ entries
 
 #### Success Page
 
-After a successful submission, visitors see a success page. The default is built into the binary from `templates/success.html`. To customise it, copy the file and point `BOOK_SUCCESS_TEMPLATE` at your copy. The `{{title}}` and `{{style}}` placeholders work the same as in the main template. Use `<script>` for dynamic behavior like showing the current time.
+```html
+<!--
+  Default success page shown after a guestbook submission.
+  Copy this file and point BOOK_SUCCESS_TEMPLATE at your copy to customize.
 
-Validation errors (empty fields, wrong captcha, etc.) show a simple error page with the error message and a back link. This page is not customisable.
+  Available placeholders:
+
+    title - Site title (BOOK_SITE_TITLE).
+    style - Custom CSS (same as the main template).
+
+  Everything else is static — write whatever you want. Use <script> for
+  dynamic behavior like showing the current time.
+-->
+<!DOCTYPE html>
+<html lang="en">
+<head>
+  <meta charset="utf-8">
+  <meta name="viewport" content="width=device-width, initial-scale=1">
+  <title>{{title}}</title>
+  {{style}}
+</head>
+<body>
+<div class="page-container">
+<p>Thanks! Your message is pending approval.</p>
+<p><a href="/">&#8592; back</a></p>
+</div>
+</body>
+</html>
+```
 
 #### Default CSS
 
@@ -410,57 +466,45 @@ Validation errors (empty fields, wrong captcha, etc.) show a simple error page w
   max-width: 70ch;
   margin: 0 auto;
   padding: 1rem;
-  white-space: pre-wrap;
   word-wrap: break-word;
 }
 
 /* Form */
-.guestbook-prompt {}
+.guestbook-prompt { display: block; margin-bottom: 1em; }
 .guestbook-form {}
-.guestbook-label {}
-.guestbook-input {}
-.guestbook-textarea {
-  box-sizing: border-box;
-}
-.guestbook-button {
-  display: block;
-  margin-top: 1em;
-}
+.guestbook-label { display: block; }
+.guestbook-input { display: block; margin-bottom: 0.5em; }
+.guestbook-textarea { display: block; box-sizing: border-box; max-width: 100%; margin-bottom: 0.5em; }
+.guestbook-button { display: block; margin-top: 1em; margin-bottom: 1.5em; }
 
 /* Drawings */
-.guestbook-canvas {
-  border: 1px solid #000;
-  cursor: crosshair;
-  display: block;
-}
-.guestbook-drawing-content {
-  display: block;
-  margin-bottom: 1em;
-}
-.entry-drawing {
-  max-width: 100%;
-}
+.guestbook-canvas { border: 1px solid #000; cursor: crosshair; display: block; max-width: 100%; height: auto; }
+.guestbook-canvas-tools { display: block; }
+.guestbook-canvas-tools a { cursor: pointer; }
+.guestbook-drawing-wrap { display: block; margin-bottom: 0.5em; }
+.guestbook-drawing-inline a { cursor: pointer; }
+.guestbook-drawing-content:empty { display: none; }
+.guestbook-drawing-content { display: block; margin-bottom: 0.5em; }
+.guestbook-swatch { display: inline-block; width: 0.85em; height: 0.85em; border: 1px solid #000; cursor: pointer; vertical-align: middle; box-sizing: border-box; margin: 0 1px; }
+.guestbook-swatch.active { border: 1px solid #000; outline: 1px solid #000; }
+.guestbook-size-slider { width: 4em; vertical-align: middle; }
+.entry-drawing { max-width: 100%; }
 
 /* Voice notes */
-.guestbook-voice-record.recording {
-  color: red;
-}
-.guestbook-voice-timer {
-  font-variant-numeric: tabular-nums;
-}
-audio {
-  display: block;
-  margin-top: 0.6em;
-  height: 2em;
-}
+.guestbook-voice-wrap { display: block; margin-bottom: 0.5em; }
+.guestbook-voice-record.recording { color: red; }
+.guestbook-voice-timer { font-variant-numeric: tabular-nums; }
+.guestbook-voice-playback:empty { display: none; }
+.guestbook-voice-playback { display: block; white-space: normal; }
+audio { display: block; margin-bottom: 0.3em; height: 2em; }
 
 /* Entries */
-.entry-header {}
+.entry { margin: 0.5em 0; }
+.entry-header { margin-bottom: 0.2em; }
 .entry-date {}
 .entry-name {}
 .entry-website {}
-.entry-body {}
-.entry-separator {}
+.entry-body { white-space: pre-wrap; }
 ```
 
 ---
diff --git a/module.nix b/module.nix
index 5ca5f51..7d54bb7 100644
--- a/module.nix
+++ b/module.nix
@@ -135,6 +135,26 @@ in
           type = types.int;
           description = "Telegram chat ID for moderation messages.";
         };
+
+        retry = {
+          interval = mkOption {
+            type = types.int;
+            default = 20;
+            description = "Seconds between retry attempts for failed Telegram notifications.";
+          };
+
+          limit = mkOption {
+            type = types.int;
+            default = 3;
+            description = "Maximum number of retry attempts for failed Telegram notifications.";
+          };
+        };
+
+        reminderInterval = mkOption {
+          type = types.int;
+          default = 86400;
+          description = "Seconds between pending entry reminders. Set to 0 to disable.";
+        };
       };
 
       security = {
@@ -322,6 +342,9 @@ in
           BOOK_SUCCESS_TEMPLATE = cfg.styles.successTemplateFile;
         } // lib.optionalAttrs cfg.features.telegram.enable {
           BOOK_TELEGRAM_CHAT_ID = toString cfg.features.telegram.chatId;
+          BOOK_TELEGRAM_RETRY_INTERVAL = toString cfg.features.telegram.retry.interval;
+          BOOK_TELEGRAM_RETRY_LIMIT = toString cfg.features.telegram.retry.limit;
+          BOOK_TELEGRAM_REMINDER_INTERVAL = toString cfg.features.telegram.reminderInterval;
         };
         serviceConfig = {
           Type = "simple";
diff --git a/src/config.rs b/src/config.rs
index 18dd157..35752bc 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -11,6 +11,12 @@ pub struct Config {
     pub telegram_bot_token: Option<String>,
     #[cfg(feature = "telegram")]
     pub telegram_chat_id: Option<i64>,
+    #[cfg(feature = "telegram")]
+    pub telegram_retry_interval: u64,
+    #[cfg(feature = "telegram")]
+    pub telegram_retry_limit: u32,
+    #[cfg(feature = "telegram")]
+    pub telegram_reminder_interval: u64,
     pub enable_honeypot: bool,
     pub max_name_length: usize,
     pub max_message_length: usize,
@@ -75,6 +81,21 @@ impl Config {
                 .ok()
                 .map(|v| v.parse().map_err(|_| "BOOK_TELEGRAM_CHAT_ID must be an integer"))
                 .transpose()?,
+            #[cfg(feature = "telegram")]
+            telegram_retry_interval: env::var("BOOK_TELEGRAM_RETRY_INTERVAL")
+                .unwrap_or_else(|_| "20".into())
+                .parse()
+                .map_err(|_| "BOOK_TELEGRAM_RETRY_INTERVAL must be a number")?,
+            #[cfg(feature = "telegram")]
+            telegram_retry_limit: env::var("BOOK_TELEGRAM_RETRY_LIMIT")
+                .unwrap_or_else(|_| "3".into())
+                .parse()
+                .map_err(|_| "BOOK_TELEGRAM_RETRY_LIMIT must be a number")?,
+            #[cfg(feature = "telegram")]
+            telegram_reminder_interval: env::var("BOOK_TELEGRAM_REMINDER_INTERVAL")
+                .unwrap_or_else(|_| "86400".into())
+                .parse()
+                .map_err(|_| "BOOK_TELEGRAM_REMINDER_INTERVAL must be a number")?,
             enable_honeypot: env::var("BOOK_ENABLE_HONEYPOT")
                 .map(|v| v != "false")
                 .unwrap_or(true),
diff --git a/src/main.rs b/src/main.rs
index 8e3db8d..fef469d 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -29,7 +29,16 @@ async fn main() {
                 let bot = Bot::new(token);
 
                 let notify_bot = bot.clone();
-                tokio::spawn(telegram::notification_task(notify_bot, chat_id, _rx));
+                let retry_interval = config.telegram_retry_interval;
+                let retry_limit = config.telegram_retry_limit;
+                tokio::spawn(telegram::notification_task(notify_bot, chat_id, _rx, retry_interval, retry_limit));
+
+                let reminder_interval = config.telegram_reminder_interval;
+                if reminder_interval > 0 {
+                    let reminder_bot = bot.clone();
+                    let reminder_data_dir = config.data_dir.clone();
+                    tokio::spawn(telegram::reminder_task(reminder_bot, chat_id, reminder_data_dir, reminder_interval));
+                }
 
                 let cmd_data_dir = config.data_dir.clone();
                 tokio::spawn(telegram::bot_task(bot, chat_id, cmd_data_dir));
diff --git a/src/render.rs b/src/render.rs
index b97961f..6de00f8 100644
--- a/src/render.rs
+++ b/src/render.rs
@@ -328,6 +328,9 @@ mod tests {
             telegram_bot_token: None,
             #[cfg(feature = "telegram")]
             telegram_chat_id: None,
+            telegram_retry_interval: 20,
+            telegram_retry_limit: 3,
+            telegram_reminder_interval: 86400,
             enable_honeypot: true,
             max_name_length: 0,
             max_message_length: 0,
diff --git a/src/telegram.rs b/src/telegram.rs
index 3df1fb3..ccd3beb 100644
--- a/src/telegram.rs
+++ b/src/telegram.rs
@@ -1,6 +1,7 @@
 use std::path::PathBuf;
 
 use teloxide::prelude::*;
+use teloxide::types::ParseMode;
 use tokio::sync::mpsc::Receiver;
 
 use crate::entries::{self, Entry, Status};
@@ -21,37 +22,126 @@ fn format_entry_list(entries: &[Entry], status_label: &str) -> String {
     lines.join("\n")
 }
 
-/// Send a notification to Telegram about a new entry.
-async fn notify(bot: &Bot, chat_id: ChatId, entry: &Entry) {
-    let text = format!(
-        "New guestbook entry:\n\nName: {}\nWebsite: {}\n\n{}\n\n/allow_{}\n/deny_{}",
-        entry.meta.name, entry.meta.website, entry.body, entry.id, entry.id
-    );
-    if let Err(e) = bot.send_message(chat_id, &text).await {
-        tracing::error!("failed to send telegram message: {e}");
+/// Escape special characters for Telegram MarkdownV2.
+fn escape_md(s: &str) -> String {
+    let special = ['_', '*', '[', ']', '(', ')', '~', '`', '>', '#', '+', '-', '=', '|', '{', '}', '.', '!'];
+    let mut out = String::with_capacity(s.len());
+    for c in s.chars() {
+        if special.contains(&c) {
+            out.push('\\');
+        }
+        out.push(c);
     }
+    out
+}
+
+/// Format a bot command, escaping underscores for MarkdownV2.
+fn cmd(name: &str, id: &str) -> String {
+    format!("/{}\\_{}", name, id)
+}
+
+/// Format an entry as a Telegram message with bold headers and contextual commands.
+fn format_entry_message(entry: &Entry) -> String {
+    let mut parts = Vec::new();
+
+    parts.push(format!("*Name*\n{}", escape_md(&entry.meta.name)));
+
+    if !entry.meta.website.is_empty() {
+        parts.push(format!("*Website*\n{}", escape_md(&entry.meta.website)));
+    }
+
+    parts.push(format!("*Message*\n{}", escape_md(&entry.body)));
+
+    // Attached media commands
+    let has_drawing = !entry.meta.drawing.is_empty();
+    let has_voice = !entry.meta.voice_note.is_empty();
+    if has_drawing || has_voice {
+        let mut attached = vec!["*Attached*".to_string()];
+        if has_drawing {
+            attached.push(cmd("drawing", &entry.id));
+        }
+        if has_voice {
+            attached.push(cmd("voice\\_note", &entry.id));
+        }
+        parts.push(attached.join("\n"));
+    }
+
+    // Moderation section with status and contextual commands
+    let status_text = match entry.meta.status {
+        Status::Pending => "Currently pending\\.",
+        Status::Approved => "Currently approved\\.",
+        Status::Denied => "Currently denied\\.",
+    };
+    let commands = match entry.meta.status {
+        Status::Pending => format!("{}\n{}", cmd("allow", &entry.id), cmd("deny", &entry.id)),
+        Status::Approved => format!("{}\n{}", cmd("deny", &entry.id), cmd("reply", &entry.id)),
+        Status::Denied => format!("{}\n{}", cmd("allow", &entry.id), cmd("delete", &entry.id)),
+    };
+    parts.push(format!("*Moderation*\n{status_text}\n\n{commands}"));
+
+    parts.join("\n\n")
+}
+
+/// Send a formatted message with Markdown parsing.
+async fn send_md(bot: &Bot, chat_id: ChatId, text: &str) -> Result<Message, teloxide::RequestError> {
+    bot.send_message(chat_id, text)
+        .parse_mode(ParseMode::MarkdownV2)
+        .await
+}
+
+/// Send a notification about a new entry, retrying on failure.
+async fn notify(bot: &Bot, chat_id: ChatId, entry: &Entry, retry_interval: u64, retry_limit: u32) {
+    let text = format_entry_message(entry);
+    if send_md(bot, chat_id, &text).await.is_ok() {
+        return;
+    }
+    tracing::warn!("failed to send notification for entry {}, spawning retry task", entry.id);
+    let bot = bot.clone();
+    let id = entry.id.clone();
+    let text = text.clone();
+    tokio::spawn(async move {
+        for attempt in 1..=retry_limit {
+            tokio::time::sleep(std::time::Duration::from_secs(retry_interval)).await;
+            tracing::info!("retry {attempt}/{retry_limit} for entry {id}");
+            match send_md(&bot, chat_id, &text).await {
+                Ok(_) => {
+                    tracing::info!("retry succeeded for entry {id}");
+                    return;
+                }
+                Err(e) => {
+                    tracing::warn!("retry {attempt}/{retry_limit} failed for entry {id}: {e}");
+                }
+            }
+        }
+        tracing::error!("all {retry_limit} retries exhausted for entry {id}");
+    });
 }
 
 /// Listen for new entries on the channel and send Telegram notifications.
-pub async fn notification_task(bot: Bot, chat_id: ChatId, mut rx: Receiver<(Entry, Option<Vec<u8>>, Option<Vec<u8>>)>) {
-    while let Some((entry, drawing_bytes, voice_bytes)) = rx.recv().await {
-        notify(&bot, chat_id, &entry).await;
-        if let Some(bytes) = drawing_bytes {
-            if let Err(e) = bot.send_photo(
-                chat_id,
-                teloxide::types::InputFile::memory(bytes).file_name("drawing.png"),
-            ).await {
-                tracing::error!("failed to send drawing photo: {e}");
-            }
-        }
-        if let Some(bytes) = voice_bytes {
-            if let Err(e) = bot.send_voice(
-                chat_id,
-                teloxide::types::InputFile::memory(bytes).file_name("voice_note.webm"),
-            ).await {
-                tracing::error!("failed to send voice note: {e}");
+pub async fn notification_task(
+    bot: Bot,
+    chat_id: ChatId,
+    mut rx: Receiver<(Entry, Option<Vec<u8>>, Option<Vec<u8>>)>,
+    retry_interval: u64,
+    retry_limit: u32,
+) {
+    while let Some((entry, _drawing_bytes, _voice_bytes)) = rx.recv().await {
+        notify(&bot, chat_id, &entry, retry_interval, retry_limit).await;
+    }
+}
+
+/// Periodically check for pending entries and send a reminder.
+pub async fn reminder_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf, interval_secs: u64) {
+    let entries_dir = data_dir.join("entries");
+    loop {
+        let pending = entries::read_by_status(&entries_dir, Status::Pending);
+        if !pending.is_empty() {
+            let text = format!("📬 *Pending reminder*\n\n{}", escape_md(&format_entry_list(&pending, "pending")));
+            if let Err(e) = send_md(&bot, chat_id, &text).await {
+                tracing::error!("failed to send pending reminder: {e}");
             }
         }
+        tokio::time::sleep(std::time::Duration::from_secs(interval_secs)).await;
     }
 }
 
@@ -69,7 +159,6 @@ pub async fn bot_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf) {
     let handler = Update::filter_message().endpoint(
         |bot: Bot, msg: Message, data_dir: PathBuf, chat_id: ChatId| async move {
             let text = msg.text().unwrap_or("");
-            // Only respond to the configured chat
             if msg.chat.id != chat_id {
                 return respond(());
             }
@@ -79,8 +168,7 @@ pub async fn bot_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf) {
             if let Some(id) = text.strip_prefix("/allow_") {
                 match entries::set_status(&entries_dir, id, Status::Approved) {
                     Ok(name) => {
-                        bot.send_message(msg.chat.id, format!("Approved ({name})."))
-                            .await?;
+                        send_md(&bot, msg.chat.id, &format!("Approved \\({}\\)\\.\n{}", escape_md(&name), cmd("reply", id))).await?;
                     }
                     Err(e) => {
                         bot.send_message(msg.chat.id, e).await?;
@@ -89,8 +177,7 @@ pub async fn bot_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf) {
             } else if let Some(id) = text.strip_prefix("/deny_") {
                 match entries::set_status(&entries_dir, id, Status::Denied) {
                     Ok(name) => {
-                        bot.send_message(msg.chat.id, format!("Denied ({name}).\n/delete_{id}"))
-                            .await?;
+                        send_md(&bot, msg.chat.id, &format!("Denied \\({}\\)\\.\n{}", escape_md(&name), cmd("delete", id))).await?;
                     }
                     Err(e) => {
                         bot.send_message(msg.chat.id, e).await?;
@@ -108,35 +195,49 @@ pub async fn bot_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf) {
             } else if let Some(id) = text.strip_prefix("/view_") {
                 match entries::find_entry(&entries_dir, id) {
                     Ok(entry) => {
-                        let text = format!(
-                            "Entry ({:?}):\n\nName: {}\nWebsite: {}\nDate: {}\n\n{}\n\n/allow_{}\n/deny_{}",
-                            entry.meta.status, entry.meta.name, entry.meta.website,
-                            entry.meta.date, entry.body, entry.id, entry.id
-                        );
-                        bot.send_message(msg.chat.id, &text).await?;
-
-                        // Send drawing if present
-                        if !entry.meta.drawing.is_empty() {
-                            let drawing_path = data_dir.join("drawings").join(&entry.meta.drawing);
-                            if let Ok(bytes) = std::fs::read(&drawing_path) {
-                                bot.send_photo(
-                                    msg.chat.id,
-                                    teloxide::types::InputFile::memory(bytes).file_name("drawing.png"),
-                                ).await.ok();
-                            }
+                        let text = format_entry_message(&entry);
+                        send_md(&bot, msg.chat.id, &text).await?;
+                    }
+                    Err(e) => {
+                        bot.send_message(msg.chat.id, e).await?;
+                    }
+                }
+            } else if let Some(id) = text.strip_prefix("/drawing_") {
+                match entries::find_entry(&entries_dir, id) {
+                    Ok(entry) if !entry.meta.drawing.is_empty() => {
+                        let drawing_path = data_dir.join("drawings").join(&entry.meta.drawing);
+                        if let Ok(bytes) = std::fs::read(&drawing_path) {
+                            bot.send_photo(
+                                msg.chat.id,
+                                teloxide::types::InputFile::memory(bytes).file_name("drawing.png"),
+                            ).await?;
+                        } else {
+                            bot.send_message(msg.chat.id, "Drawing file not found.").await?;
                         }
-
-                        // Send voice note if present
-                        if !entry.meta.voice_note.is_empty() {
-                            let vn_path = data_dir.join("voice_notes").join(&entry.meta.voice_note);
-                            if let Ok(bytes) = std::fs::read(&vn_path) {
-                                bot.send_voice(
-                                    msg.chat.id,
-                                    teloxide::types::InputFile::memory(bytes).file_name("voice_note.webm"),
-                                ).await.ok();
-                            }
+                    }
+                    Ok(_) => {
+                        bot.send_message(msg.chat.id, "No drawing attached.").await?;
+                    }
+                    Err(e) => {
+                        bot.send_message(msg.chat.id, e).await?;
+                    }
+                }
+            } else if let Some(id) = text.strip_prefix("/voice_note_") {
+                match entries::find_entry(&entries_dir, id) {
+                    Ok(entry) if !entry.meta.voice_note.is_empty() => {
+                        let vn_path = data_dir.join("voice_notes").join(&entry.meta.voice_note);
+                        if let Ok(bytes) = std::fs::read(&vn_path) {
+                            bot.send_voice(
+                                msg.chat.id,
+                                teloxide::types::InputFile::memory(bytes).file_name("voice_note.webm"),
+                            ).await?;
+                        } else {
+                            bot.send_message(msg.chat.id, "Voice note file not found.").await?;
                         }
                     }
+                    Ok(_) => {
+                        bot.send_message(msg.chat.id, "No voice note attached.").await?;
+                    }
                     Err(e) => {
                         bot.send_message(msg.chat.id, e).await?;
                     }
@@ -145,8 +246,7 @@ pub async fn bot_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf) {
                 let (id, reply) = match rest.split_once('\n') {
                     Some((id, reply)) => (id.trim(), reply),
                     None => {
-                        bot.send_message(msg.chat.id, "Usage: /reply_ID\\nYour reply text")
-                            .await?;
+                        bot.send_message(msg.chat.id, "Usage: /reply_ID\nYour reply text").await?;
                         return respond(());
                     }
                 };
@@ -163,7 +263,7 @@ pub async fn bot_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf) {
                         bot.send_message(msg.chat.id, e).await?;
                     }
                 }
-            } else if let Some(id) = text.strip_prefix("/delete_") {
+            } else if let Some(id) = text.strip_prefix("/confirm_delete_") {
                 match entries::delete_entry(&data_dir, id) {
                     Ok(name) => {
                         bot.send_message(msg.chat.id, format!("Deleted ({name}).")).await?;
@@ -172,6 +272,18 @@ pub async fn bot_task(bot: Bot, chat_id: ChatId, data_dir: PathBuf) {
                         bot.send_message(msg.chat.id, e).await?;
                     }
                 }
+            } else if let Some(id) = text.strip_prefix("/delete_") {
+                match entries::find_entry(&entries_dir, id) {
+                    Ok(entry) => {
+                        bot.send_message(
+                            msg.chat.id,
+                            format!("Delete {}'s entry? This cannot be undone.\n\n/confirm_delete_{}", entry.meta.name, entry.id),
+                        ).await?;
+                    }
+                    Err(e) => {
+                        bot.send_message(msg.chat.id, e).await?;
+                    }
+                }
             }
 
             Ok(())
diff --git a/src/web.rs b/src/web.rs
index d5dca4b..307424f 100644
--- a/src/web.rs
+++ b/src/web.rs
@@ -358,6 +358,9 @@ mod tests {
             telegram_bot_token: None,
             #[cfg(feature = "telegram")]
             telegram_chat_id: None,
+            telegram_retry_interval: 20,
+            telegram_retry_limit: 3,
+            telegram_reminder_interval: 86400,
             enable_honeypot: true,
             max_name_length: 0,
             max_message_length: 0,
diff --git a/templates/default.html b/templates/default.html
index 4ed31b8..a517a98 100644
--- a/templates/default.html
+++ b/templates/default.html
@@ -14,8 +14,7 @@
               BOOK_LABEL_NAME, BOOK_LABEL_WEBSITE, BOOK_LABEL_MESSAGE,
               BOOK_BUTTON_TEXT, BOOK_TEXTAREA_WIDTH, BOOK_TEXTAREA_HEIGHT.
               Empty when BOOK_ENABLE_SUBMISSIONS=false.
-    entries - Approved guestbook entries, newest first. Entry separator
-              controlled by BOOK_SEPARATOR.
+    entries - Approved guestbook entries, newest first.
     style   - Custom CSS from BOOK_STYLE or BOOK_STYLE_FILE, wrapped in
               a <style> tag. Uses built-in default.css when neither is set.
 
@@ -32,8 +31,6 @@
 <body>
 <div class="page-container">
 {{title}}
-
-guestbook
 =========
 
 {{prompt}}