feat: Add notification sound functionality and embed support

- Introduced NotificationConfig to manage notification settings, including sound file.
- Added Notification.mp3 asset for notifications.
- Implemented NotificationSoundService to handle playing notification sounds.
- Enhanced ChatRenderer and MainWindow to support emoji rendering.
- Updated MessageDto to allow multiple embeds per message.
- Modified LinkEmbedService to fetch multiple embeds from message content.
- Added data migration for legacy embed JSON format to new array format.
- Adjusted embed handling in ChatService and IrcMessageFormatter to accommodate multiple embeds.
- Updated HubConstants for new embed dimensions and limits.

docs/changelog/v0.2.4.md

@@ -0,0 +1,22 @@
+# v0.2.4 - Link Embeds
+
+## Features
+
+### OpenGraph Link Embeds
+- Messages containing URLs now show a rich preview below the message text, similar to Discord
+- Server-side fetching: detects the first URL in a message, fetches the page, and parses OpenGraph meta tags (`og:title`, `og:description`, `og:image`, `og:site_name`)
+- OG images are converted to a small 24x12 colored ASCII thumbnail using the existing half-block renderer
+- Embeds are persisted in the database and included in channel history
+- TUI client renders embeds with a `▏` left border bar — site name and border in blue, title in white, description in gray, followed by the ASCII thumbnail
+- IRC gateway receives a text-only embed preview (site name, title, description) — no ASCII thumbnail to keep IRC output clean
+- Falls back to `<title>` tag when no OG tags are present; gracefully skips if no useful metadata is found
+- 3-second fetch timeout ensures message delivery is never significantly delayed
+- SSRF protection rejects private/loopback IP addresses before fetching
+
+## Infrastructure
+
+- New `LinkEmbedService` on the server — URL detection, HTML fetching (first 64KB), OG tag parsing via regex, image thumbnail generation
+- `EmbedDto` record added to shared Core DTOs; `MessageDto` extended with optional `Embed` field (backward-compatible)
+- `EmbedJson` nullable column on the `Message` table stores serialized embed data (max 8KB)
+- Dedicated `"OgFetch"` named HttpClient with bot User-Agent header and 5-second timeout
+- New EF Core migration: `AddMessageEmbed`

src/EchoHub.Client/Config/ClientConfig.cs

@@ -5,6 +5,13 @@ public class ClientConfig
     public List<SavedServer> SavedServers { get; set; } = [];
     public AccountPreset DefaultPreset { get; set; } = new();
     public string ActiveTheme { get; set; } = "Default";
+    public NotificationConfig Notifications { get; set; } = new();
+}
+
+public class NotificationConfig
+{
+    public bool Enabled { get; set; } = true;
+    public string? SoundFile { get; set; }
 }
 
 public class SavedServer

src/EchoHub.Client/EchoHub.Client.csproj

@@ -7,6 +7,7 @@
   <ItemGroup>
     <PackageReference Include="Microsoft.AspNetCore.SignalR.Client" Version="10.0.3" />
     <PackageReference Include="Microsoft.Extensions.Configuration.Json" Version="10.0.3" />
+    <PackageReference Include="NetCoreAudio" Version="2.0.1" />
     <PackageReference Include="Serilog" Version="4.3.1" />
     <PackageReference Include="Serilog.Settings.Configuration" Version="10.0.0" />
     <PackageReference Include="Serilog.Sinks.File" Version="7.0.0" />
@@ -17,6 +18,9 @@
     <Content Include="appsettings.json" Condition="Exists('appsettings.json')">
       <CopyToOutputDirectory>PreserveNewest</CopyToOutputDirectory>
     </Content>
+    <Content Include="Assets\**">
+      <CopyToOutputDirectory>PreserveNewest</CopyToOutputDirectory>
+    </Content>
     <EmbeddedResource Include="appsettings.example.json">
       <LogicalName>EchoHub.Client.appsettings.example.json</LogicalName>
     </EmbeddedResource>

src/EchoHub.Client/Services/NotificationSoundService.cs

@@ -0,0 +1,64 @@
+using EchoHub.Client.Config;
+using NetCoreAudio;
+using Serilog;
+
+namespace EchoHub.Client.Services;
+
+public class NotificationSoundService
+{
+    private readonly Player _player = new();
+    private readonly NotificationConfig _config;
+    private string? _resolvedSoundPath;
+
+    public NotificationSoundService(NotificationConfig config)
+    {
+        _config = config;
+        ResolveSoundPath();
+    }
+
+    public async Task PlayAsync()
+    {
+        if (!_config.Enabled || _resolvedSoundPath is null)
+            return;
+
+        try
+        {
+            if (_player.Playing)
+                await _player.Stop();
+
+            await _player.Play(_resolvedSoundPath);
+        }
+        catch (Exception ex)
+        {
+            Log.Warning(ex, "Failed to play notification sound");
+        }
+    }
+
+    private void ResolveSoundPath()
+    {
+        // 1. Explicit path from config (~/.echohub/config.json)
+        if (!string.IsNullOrWhiteSpace(_config.SoundFile))
+        {
+            if (File.Exists(_config.SoundFile))
+            {
+                _resolvedSoundPath = Path.GetFullPath(_config.SoundFile);
+                Log.Debug("Notification sound: {Path} (from config)", _resolvedSoundPath);
+                return;
+            }
+
+            Log.Warning("Configured sound file not found: {Path}", _config.SoundFile);
+        }
+
+        // 2. Default: Notification.mp3 bundled next to the executable
+        var defaultPath = Path.Combine(AppContext.BaseDirectory, "Assets", "Notification.mp3");
+
+        if (File.Exists(defaultPath))
+        {
+            _resolvedSoundPath = defaultPath;
+            Log.Debug("Notification sound: {Path} (default)", _resolvedSoundPath);
+            return;
+        }
+
+        Log.Information("No notification sound file found — notifications will be silent");
+    }
+}

src/EchoHub.Client/UI/ChatRenderer.cs

@@ -101,6 +101,12 @@ public partial class ChatLine
     public static bool HasColorTags(string text) =>
         text.Contains("{F:") || text.Contains("{B:") || text.Contains("{X}");
 
+    /// <summary>
+    /// Remove all color tags from text, returning only the visible characters.
+    /// </summary>
+    public static string StripColorTags(string text) =>
+        ColorTagRegex().Replace(text, "");
+
     /// <summary>
     /// Parse a string containing printable color tags into colored segments.
     /// Format: {F:RRGGBB} (foreground), {B:RRGGBB} (background), {X} (reset).
@@ -458,6 +464,7 @@ public static partial class ChatColors
     public static readonly Attribute EmbedBorderAttr = new(new Color(91, 155, 213), Color.Black);
     public static readonly Attribute EmbedTitleAttr = new(Color.White, Color.Black);
     public static readonly Attribute EmbedDescAttr = new(new Color(160, 160, 160), Color.Black);
+    public static readonly Attribute EmbedUrlAttr = new(new Color(100, 100, 100), Color.Black);
 
     /// <summary>
     /// Split text around @mentions, giving each @word the MentionTextAttr accent color.

src/EchoHub.Client/UI/EmojiHelper.cs

@@ -0,0 +1,333 @@
+using System.Globalization;
+using System.Text;
+
+namespace EchoHub.Client.UI;
+
+/// <summary>
+/// Converts emoji grapheme clusters to text shortcodes for safe TUI rendering.
+/// Terminal width calculations for emoji are unreliable across different terminals,
+/// so we replace them with fixed-width ASCII shortcodes for display only.
+/// </summary>
+public static class EmojiHelper
+{
+    /// <summary>
+    /// Replace emoji graphemes in the text with :shortcode: equivalents.
+    /// Non-emoji text passes through unchanged.
+    /// </summary>
+    public static string ReplaceEmoji(string text)
+    {
+        if (string.IsNullOrEmpty(text))
+            return text;
+
+        // Quick check: if no characters above BMP or supplementary emoji ranges, skip processing
+        bool hasEmoji = false;
+        foreach (var rune in text.EnumerateRunes())
+        {
+            if (IsEmojiRune(rune))
+            {
+                hasEmoji = true;
+                break;
+            }
+        }
+
+        if (!hasEmoji)
+            return text;
+
+        var sb = new StringBuilder(text.Length);
+        var enumerator = StringInfo.GetTextElementEnumerator(text);
+
+        while (enumerator.MoveNext())
+        {
+            var grapheme = enumerator.GetTextElement();
+
+            // Check if this grapheme contains emoji runes
+            bool graphemeHasEmoji = false;
+            foreach (var rune in grapheme.EnumerateRunes())
+            {
+                if (IsEmojiRune(rune))
+                {
+                    graphemeHasEmoji = true;
+                    break;
+                }
+            }
+
+            if (graphemeHasEmoji)
+            {
+                // Try to find a shortcode for the whole grapheme first
+                if (EmojiShortcodes.TryGetValue(grapheme, out var shortcode))
+                {
+                    sb.Append(shortcode);
+                }
+                else
+                {
+                    // Try the base emoji (first rune only, stripping modifiers/ZWJ)
+                    var baseRune = GetBaseEmoji(grapheme);
+                    if (baseRune is not null && EmojiShortcodes.TryGetValue(baseRune, out shortcode))
+                    {
+                        sb.Append(shortcode);
+                    }
+                    else
+                    {
+                        // Unknown emoji — use generic placeholder
+                        sb.Append("[emoji]");
+                    }
+                }
+            }
+            else
+            {
+                sb.Append(grapheme);
+            }
+        }
+
+        return sb.ToString();
+    }
+
+    private static bool IsEmojiRune(Rune rune)
+    {
+        var value = rune.Value;
+
+        // Common emoji ranges
+        if (value >= 0x1F600 && value <= 0x1F64F) return true; // Emoticons
+        if (value >= 0x1F300 && value <= 0x1F5FF) return true; // Misc Symbols & Pictographs
+        if (value >= 0x1F680 && value <= 0x1F6FF) return true; // Transport & Map
+        if (value >= 0x1F900 && value <= 0x1F9FF) return true; // Supplemental Symbols
+        if (value >= 0x1FA00 && value <= 0x1FA6F) return true; // Chess Symbols
+        if (value >= 0x1FA70 && value <= 0x1FAFF) return true; // Symbols Extended-A
+        if (value >= 0x2600 && value <= 0x26FF) return true;   // Misc Symbols
+        if (value >= 0x2700 && value <= 0x27BF) return true;   // Dingbats
+        if (value >= 0xFE00 && value <= 0xFE0F) return true;   // Variation Selectors
+        if (value >= 0x200D && value <= 0x200D) return true;   // ZWJ
+        if (value >= 0x1F1E0 && value <= 0x1F1FF) return true; // Regional Indicators (flags)
+        if (value >= 0x231A && value <= 0x23F3) return true;   // Misc Technical (watch, hourglass)
+        if (value >= 0x2934 && value <= 0x2935) return true;   // Arrows
+        if (value >= 0x25AA && value <= 0x25FE) return true;   // Geometric Shapes
+        if (value >= 0x2B05 && value <= 0x2B55) return true;   // Misc Symbols & Arrows
+        if (value >= 0x3030 && value <= 0x303D) return true;   // CJK Symbols
+        if (value == 0x00A9 || value == 0x00AE) return true;   // © ®
+        if (value == 0x2122) return true;                       // ™
+        if (value >= 0x1F000 && value <= 0x1F02F) return true;  // Mahjong & Dominos
+
+        return false;
+    }
+
+    /// <summary>
+    /// Extract the base emoji string (first non-modifier, non-ZWJ rune) for lookup.
+    /// </summary>
+    private static string? GetBaseEmoji(string grapheme)
+    {
+        foreach (var rune in grapheme.EnumerateRunes())
+        {
+            // Skip ZWJ, variation selectors, skin tone modifiers
+            if (rune.Value == 0x200D) continue;
+            if (rune.Value >= 0xFE00 && rune.Value <= 0xFE0F) continue;
+            if (rune.Value >= 0x1F3FB && rune.Value <= 0x1F3FF) continue;
+
+            if (IsEmojiRune(rune))
+                return rune.ToString();
+        }
+
+        return null;
+    }
+
+    // Common emoji → shortcode mapping (display-only, covers most frequently used emoji)
+    private static readonly Dictionary<string, string> EmojiShortcodes = new()
+    {
+        // Smileys & Emotion
+        ["\U0001F600"] = ":grinning:",
+        ["\U0001F601"] = ":grin:",
+        ["\U0001F602"] = ":joy:",
+        ["\U0001F603"] = ":smiley:",
+        ["\U0001F604"] = ":smile:",
+        ["\U0001F605"] = ":sweat_smile:",
+        ["\U0001F606"] = ":laughing:",
+        ["\U0001F607"] = ":innocent:",
+        ["\U0001F608"] = ":smiling_imp:",
+        ["\U0001F609"] = ":wink:",
+        ["\U0001F60A"] = ":blush:",
+        ["\U0001F60B"] = ":yum:",
+        ["\U0001F60C"] = ":relieved:",
+        ["\U0001F60D"] = ":heart_eyes:",
+        ["\U0001F60E"] = ":sunglasses:",
+        ["\U0001F60F"] = ":smirk:",
+        ["\U0001F610"] = ":neutral_face:",
+        ["\U0001F611"] = ":expressionless:",
+        ["\U0001F612"] = ":unamused:",
+        ["\U0001F613"] = ":sweat:",
+        ["\U0001F614"] = ":pensive:",
+        ["\U0001F615"] = ":confused:",
+        ["\U0001F616"] = ":confounded:",
+        ["\U0001F617"] = ":kissing:",
+        ["\U0001F618"] = ":kissing_heart:",
+        ["\U0001F619"] = ":kissing_smiling_eyes:",
+        ["\U0001F61A"] = ":kissing_closed_eyes:",
+        ["\U0001F61B"] = ":stuck_out_tongue:",
+        ["\U0001F61C"] = ":stuck_out_tongue_winking_eye:",
+        ["\U0001F61D"] = ":stuck_out_tongue_closed_eyes:",
+        ["\U0001F61E"] = ":disappointed:",
+        ["\U0001F61F"] = ":worried:",
+        ["\U0001F620"] = ":angry:",
+        ["\U0001F621"] = ":rage:",
+        ["\U0001F622"] = ":cry:",
+        ["\U0001F623"] = ":persevere:",
+        ["\U0001F624"] = ":triumph:",
+        ["\U0001F625"] = ":disappointed_relieved:",
+        ["\U0001F626"] = ":frowning:",
+        ["\U0001F627"] = ":anguished:",
+        ["\U0001F628"] = ":fearful:",
+        ["\U0001F629"] = ":weary:",
+        ["\U0001F62A"] = ":sleepy:",
+        ["\U0001F62B"] = ":tired_face:",
+        ["\U0001F62C"] = ":grimacing:",
+        ["\U0001F62D"] = ":sob:",
+        ["\U0001F62E"] = ":open_mouth:",
+        ["\U0001F62F"] = ":hushed:",
+        ["\U0001F630"] = ":cold_sweat:",
+        ["\U0001F631"] = ":scream:",
+        ["\U0001F632"] = ":astonished:",
+        ["\U0001F633"] = ":flushed:",
+        ["\U0001F634"] = ":sleeping:",
+        ["\U0001F635"] = ":dizzy_face:",
+        ["\U0001F636"] = ":no_mouth:",
+        ["\U0001F637"] = ":mask:",
+        ["\U0001F641"] = ":slightly_frowning_face:",
+        ["\U0001F642"] = ":slightly_smiling_face:",
+        ["\U0001F643"] = ":upside_down_face:",
+        ["\U0001F644"] = ":roll_eyes:",
+        ["\U0001F910"] = ":zipper_mouth:",
+        ["\U0001F911"] = ":money_mouth:",
+        ["\U0001F912"] = ":thermometer_face:",
+        ["\U0001F913"] = ":nerd:",
+        ["\U0001F914"] = ":thinking:",
+        ["\U0001F915"] = ":head_bandage:",
+        ["\U0001F920"] = ":cowboy:",
+        ["\U0001F921"] = ":clown:",
+        ["\U0001F922"] = ":nauseated:",
+        ["\U0001F923"] = ":rofl:",
+        ["\U0001F924"] = ":drooling:",
+        ["\U0001F925"] = ":lying:",
+        ["\U0001F929"] = ":star_struck:",
+        ["\U0001F92A"] = ":zany:",
+        ["\U0001F92B"] = ":shushing:",
+        ["\U0001F92C"] = ":cursing:",
+        ["\U0001F92D"] = ":hand_over_mouth:",
+        ["\U0001F92E"] = ":vomiting:",
+        ["\U0001F92F"] = ":exploding_head:",
+        ["\U0001F970"] = ":smiling_face_with_hearts:",
+        ["\U0001F971"] = ":yawning:",
+        ["\U0001F972"] = ":smiling_with_tear:",
+        ["\U0001F973"] = ":partying:",
+        ["\U0001F974"] = ":woozy:",
+        ["\U0001F975"] = ":hot_face:",
+        ["\U0001F976"] = ":cold_face:",
+        ["\U0001F979"] = ":holding_back_tears:",
+        ["\U0001F97A"] = ":pleading:",
+        ["\U0001FAE0"] = ":melting:",
+        ["\U0001FAE1"] = ":saluting:",
+        ["\U0001FAE2"] = ":face_with_open_eyes_hand_over_mouth:",
+        ["\U0001FAE3"] = ":face_with_peeking_eye:",
+        ["\U0001FAE4"] = ":face_with_diagonal_mouth:",
+
+        // Gestures
+        ["\U0001F44D"] = ":+1:",
+        ["\U0001F44E"] = ":-1:",
+        ["\U0001F44B"] = ":wave:",
+        ["\U0001F44C"] = ":ok_hand:",
+        ["\U0001F44F"] = ":clap:",
+        ["\U0001F44A"] = ":fist:",
+        ["\U0001F91D"] = ":handshake:",
+        ["\U0001F91E"] = ":crossed_fingers:",
+        ["\U0001F91F"] = ":love_you:",
+        ["\U0001F918"] = ":metal:",
+        ["\U0001F919"] = ":call_me:",
+        ["\U0001F590"] = ":raised_hand:",
+        ["\U0001F4AA"] = ":muscle:",
+        ["\U0001F926"] = ":facepalm:",
+        ["\U0001F937"] = ":shrug:",
+        ["\U0001F64F"] = ":pray:",
+        ["\U0001F64C"] = ":raised_hands:",
+        ["\U0001F64B"] = ":raising_hand:",
+
+        // Hearts & Symbols
+        ["\u2764"] = "<3",
+        ["\U0001F494"] = "</3",
+        ["\U0001F495"] = ":two_hearts:",
+        ["\U0001F496"] = ":sparkling_heart:",
+        ["\U0001F497"] = ":heartpulse:",
+        ["\U0001F498"] = ":cupid:",
+        ["\U0001F499"] = ":blue_heart:",
+        ["\U0001F49A"] = ":green_heart:",
+        ["\U0001F49B"] = ":yellow_heart:",
+        ["\U0001F49C"] = ":purple_heart:",
+        ["\U0001F49D"] = ":gift_heart:",
+        ["\U0001F49E"] = ":revolving_hearts:",
+        ["\U0001F49F"] = ":heart_decoration:",
+        ["\U0001F90D"] = ":white_heart:",
+        ["\U0001F90E"] = ":brown_heart:",
+        ["\U0001F5A4"] = ":black_heart:",
+        ["\U0001F9E1"] = ":orange_heart:",
+
+        // Objects & Nature
+        ["\U0001F525"] = ":fire:",
+        ["\U0001F4A9"] = ":poop:",
+        ["\U0001F480"] = ":skull:",
+        ["\U0001F47B"] = ":ghost:",
+        ["\U0001F47D"] = ":alien:",
+        ["\U0001F916"] = ":robot:",
+        ["\U0001F4AF"] = ":100:",
+        ["\U0001F4A5"] = ":boom:",
+        ["\U0001F4A4"] = ":zzz:",
+        ["\U0001F4A2"] = ":anger:",
+        ["\U0001F4AC"] = ":speech_balloon:",
+        ["\U0001F440"] = ":eyes:",
+        ["\U0001F3B5"] = ":musical_note:",
+        ["\U0001F3B6"] = ":notes:",
+        ["\U0001F389"] = ":tada:",
+        ["\U0001F38A"] = ":confetti:",
+        ["\U0001F381"] = ":gift:",
+        ["\U0001F3C6"] = ":trophy:",
+        ["\U0001F4B0"] = ":money_bag:",
+        ["\U0001F4BB"] = ":computer:",
+        ["\U0001F4F1"] = ":phone:",
+        ["\U0001F4E7"] = ":email:",
+        ["\U0001F511"] = ":key:",
+        ["\U0001F512"] = ":lock:",
+        ["\U0001F513"] = ":unlock:",
+        ["\U0001F6A8"] = ":rotating_light:",
+        ["\U0001F6AB"] = ":no_entry:",
+
+        // Animals
+        ["\U0001F436"] = ":dog:",
+        ["\U0001F431"] = ":cat:",
+        ["\U0001F42D"] = ":mouse:",
+        ["\U0001F430"] = ":rabbit:",
+        ["\U0001F43B"] = ":bear:",
+        ["\U0001F427"] = ":penguin:",
+        ["\U0001F41D"] = ":bee:",
+        ["\U0001F40D"] = ":snake:",
+        ["\U0001F422"] = ":turtle:",
+
+        // Food & Drink
+        ["\U0001F355"] = ":pizza:",
+        ["\U0001F354"] = ":hamburger:",
+        ["\U0001F37A"] = ":beer:",
+        ["\U0001F377"] = ":wine:",
+        ["\U0001F370"] = ":cake:",
+        ["\u2615"] = ":coffee:",
+        ["\U0001F382"] = ":birthday:",
+
+        // Misc symbols (BMP)
+        ["\u2705"] = ":white_check_mark:",
+        ["\u274C"] = ":x:",
+        ["\u274E"] = ":negative_squared_cross_mark:",
+        ["\u2714"] = ":heavy_check_mark:",
+        ["\u2716"] = ":heavy_multiplication_x:",
+        ["\u26A0"] = ":warning:",
+        ["\u2B50"] = ":star:",
+        ["\u2728"] = ":sparkles:",
+        ["\u267B"] = ":recycle:",
+        ["\u2611"] = ":ballot_box_with_check:",
+        ["\u23F0"] = ":alarm_clock:",
+        ["\u231A"] = ":watch:",
+        ["\u231B"] = ":hourglass:",
+    };
+}

src/EchoHub.Client/UI/MainWindow.cs

@@ -4,7 +4,9 @@ using EchoHub.Core.DTOs;
 using EchoHub.Core.Models;
 using Terminal.Gui.App;
 using Terminal.Gui.Configuration;
+using Terminal.Gui.Drawing;
 using Terminal.Gui.Input;
+using Terminal.Gui.Text;
 using Terminal.Gui.ViewBase;
 using Terminal.Gui.Views;
 using Attribute = Terminal.Gui.Drawing.Attribute;
@@ -880,7 +882,8 @@ public sealed class MainWindow : Runnable
 
             case MessageType.Text:
             default:
-                var contentLines = message.Content.Split('\n');
+                var displayContent = EmojiHelper.ReplaceEmoji(message.Content);
+                var contentLines = displayContent.Split('\n');
                 var firstLine = contentLines[0].TrimEnd('\r');
                 lines.Add(BuildChatLineWithMentions(time, senderName, senderColor, $" {firstLine}"));
                 // Continuation lines indented to align with first line's content
@@ -891,9 +894,12 @@ public sealed class MainWindow : Runnable
                     lines.Add(new ChatLine(ChatColors.SplitMentions(contText)));
                 }
 
-                // Render link embed if present
+                // Render link embeds if present
-                if (message.Embed is not null)
+                if (message.Embeds is { Count: > 0 })
-                    lines.AddRange(FormatEmbed(message.Embed, indent));
+                {
+                    foreach (var embed in message.Embeds)
+                        lines.AddRange(FormatEmbed(embed, indent));
+                }
                 break;
         }
 
@@ -944,65 +950,152 @@ public sealed class MainWindow : Runnable
     }
 
     /// <summary>
-    /// Format a link embed as indented chat lines with a left border bar.
+    /// Format a link embed as indented chat lines with a left border bar,
+    /// optional description wrapping, and a small icon on the right (Discord-style).
+    /// Layout: ▏ {text column}  {icon column}
     /// </summary>
     private static List<ChatLine> FormatEmbed(EmbedDto embed, string indent)
     {
         var lines = new List<ChatLine>();
         const string border = "\u258f "; // ▏ + space
+        const int borderCols = 2; // ▏ = 1 col + space = 1 col
+        const int iconGap = 1; // space between text and icon
 
-        // Site name
+        // Parse icon lines if present
-        if (!string.IsNullOrWhiteSpace(embed.SiteName))
+        var iconLines = new List<string>();
-        {
+        int iconWidth = 0;
-            lines.Add(new ChatLine(new List<ChatSegment>
-            {
-                new(indent, null),
-                new(border, ChatColors.EmbedBorderAttr),
-                new(embed.SiteName, ChatColors.EmbedBorderAttr)
-            }));
-        }
-
-        // Title
-        if (!string.IsNullOrWhiteSpace(embed.Title))
-        {
-            lines.Add(new ChatLine(new List<ChatSegment>
-            {
-                new(indent, null),
-                new(border, ChatColors.EmbedBorderAttr),
-                new(embed.Title, ChatColors.EmbedTitleAttr)
-            }));
-        }
-
-        // Description (truncated)
-        if (!string.IsNullOrWhiteSpace(embed.Description))
-        {
-            var desc = embed.Description.Length > 120
-                ? embed.Description[..117] + "..."
-                : embed.Description;
-
-            lines.Add(new ChatLine(new List<ChatSegment>
-            {
-                new(indent, null),
-                new(border, ChatColors.EmbedBorderAttr),
-                new(desc, ChatColors.EmbedDescAttr)
-            }));
-        }
-
-        // ASCII image thumbnail
         if (!string.IsNullOrWhiteSpace(embed.ImageAscii))
         {
             foreach (var artLine in embed.ImageAscii.Split('\n'))
             {
                 var trimmed = artLine.TrimEnd('\r');
-                if (string.IsNullOrEmpty(trimmed)) continue;
+                if (!string.IsNullOrEmpty(trimmed))
-
+                    iconLines.Add(trimmed);
-                if (ChatLine.HasColorTags(trimmed))
-                    lines.Add(ChatLine.FromColoredText(indent + border + trimmed));
-                else
-                    lines.Add(new ChatLine(indent + border + trimmed));
             }
+            if (iconLines.Count > 0)
+            {
+                // Measure icon width from the first line (strip color tags for measurement)
+                var stripped = ChatLine.StripColorTags(iconLines[0]);
+                iconWidth = stripped.GetColumns();
+            }
+        }
+
+        bool hasIcon = iconLines.Count > 0 && iconWidth > 0;
+        int indentCols = indent.GetColumns();
+
+        // We don't know the terminal width at format time, so use a reasonable default
+        // for text wrapping. The ChatListSource.Render will handle final clipping.
+        const int estimatedWidth = 80;
+        int availableForText = estimatedWidth - indentCols - borderCols;
+        int textColWidth = hasIcon
+            ? availableForText - iconWidth - iconGap
+            : availableForText;
+        if (textColWidth < 20) textColWidth = 20;
+
+        // Collect all text rows (site name, title, wrapped description, URL)
+        var textRows = new List<(string Text, Attribute? Color)>();
+
+        if (!string.IsNullOrWhiteSpace(embed.SiteName))
+            textRows.Add((embed.SiteName, ChatColors.EmbedBorderAttr));
+
+        if (!string.IsNullOrWhiteSpace(embed.Title))
+            textRows.Add((embed.Title, ChatColors.EmbedTitleAttr));
+
+        // Word-wrap description
+        if (!string.IsNullOrWhiteSpace(embed.Description))
+        {
+            foreach (var wrappedLine in WordWrap(embed.Description, textColWidth))
+                textRows.Add((wrappedLine, ChatColors.EmbedDescAttr));
+        }
+
+        // Dim URL at the bottom
+        textRows.Add((embed.Url, ChatColors.EmbedUrlAttr));
+
+        // Merge text rows with icon rows side-by-side
+        int totalLines = Math.Max(textRows.Count, iconLines.Count);
+        for (int i = 0; i < totalLines; i++)
+        {
+            var segments = new List<ChatSegment>();
+            segments.Add(new ChatSegment(indent, null));
+            segments.Add(new ChatSegment(border, ChatColors.EmbedBorderAttr));
+
+            if (i < textRows.Count)
+            {
+                var (text, color) = textRows[i];
+                segments.Add(new ChatSegment(text, color));
+
+                // Pad to align icon column
+                if (hasIcon && i < iconLines.Count)
+                {
+                    int textCols = text.GetColumns();
+                    int padding = textColWidth - textCols + iconGap;
+                    if (padding > 0)
+                        segments.Add(new ChatSegment(new string(' ', padding), null));
+                }
+            }
+            else if (hasIcon && i < iconLines.Count)
+            {
+                // No text row, pad the full text column + gap
+                segments.Add(new ChatSegment(new string(' ', textColWidth + iconGap), null));
+            }
+
+            // Append icon line
+            if (hasIcon && i < iconLines.Count)
+            {
+                var iconLine = iconLines[i];
+                if (ChatLine.HasColorTags(iconLine))
+                {
+                    // Build a composite: plain segments + colored icon
+                    var plainPart = new ChatLine(segments);
+                    var iconPart = ChatLine.FromColoredText(iconLine);
+                    var merged = new List<ChatSegment>(plainPart.Segments);
+                    merged.AddRange(iconPart.Segments);
+                    lines.Add(new ChatLine(merged));
+                    continue;
+                }
+                else
+                {
+                    segments.Add(new ChatSegment(iconLine, null));
+                }
+            }
+
+            lines.Add(new ChatLine(segments));
         }
 
         return lines;
     }
+
+    /// <summary>
+    /// Simple word-wrap: splits text into lines that fit within maxCols display columns.
+    /// </summary>
+    private static List<string> WordWrap(string text, int maxCols)
+    {
+        if (maxCols <= 0)
+            return [text];
+
+        var result = new List<string>();
+        var words = text.Split(' ', StringSplitOptions.RemoveEmptyEntries);
+        var currentLine = "";
+
+        foreach (var word in words)
+        {
+            var candidate = currentLine.Length == 0 ? word : currentLine + " " + word;
+            if (candidate.GetColumns() <= maxCols)
+            {
+                currentLine = candidate;
+            }
+            else
+            {
+                if (currentLine.Length > 0)
+                    result.Add(currentLine);
+                // If a single word exceeds maxCols, just add it as-is
+                currentLine = word;
+            }
+        }
+
+        if (currentLine.Length > 0)
+            result.Add(currentLine);
+
+        return result;
+    }
 }

src/EchoHub.Core/Constants/HubConstants.cs

@@ -15,9 +15,10 @@ public static class HubConstants
     public const int AsciiArtHeightHalfBlock = 80;
 
     // Link embed constants
-    public const int EmbedThumbnailWidth = 24;
+    public const int EmbedIconWidth = 12;
-    public const int EmbedThumbnailHeight = 12;
+    public const int EmbedIconHeight = 6;
-    public const int EmbedMaxDescriptionLength = 200;
+    public const int EmbedMaxDescriptionLength = 500;
     public const int EmbedMaxHtmlBytes = 64 * 1024; // 64 KB
     public const int EmbedFetchTimeoutSeconds = 3;
+    public const int EmbedMaxUrlsPerMessage = 3;
 }

src/EchoHub.Core/DTOs/ChatDtos.cs

@@ -12,7 +12,7 @@ public record MessageDto(
     string? AttachmentUrl,
     string? AttachmentFileName,
     DateTimeOffset SentAt,
-    EmbedDto? Embed = null);
+    List<EmbedDto>? Embeds = null);
 
 public record ChannelDto(
     Guid Id,

src/EchoHub.Server.Irc/IrcMessageFormatter.cs

@@ -24,9 +24,12 @@ public static partial class IrcMessageFormatter
                 foreach (var chunk in SplitMessage(message.Content, MaxIrcLineContentBytes))
                     lines.Add($"{prefix} PRIVMSG {ircChannel} :{chunk}");
 
-                // Append embed preview if present
+                // Append embed previews if present
-                if (message.Embed is not null)
+                if (message.Embeds is { Count: > 0 })
-                    lines.AddRange(FormatEmbed(prefix, ircChannel, message.Embed));
+                {
+                    foreach (var embed in message.Embeds)
+                        lines.AddRange(FormatEmbed(prefix, ircChannel, embed));
+                }
                 break;
 
             case MessageType.Image:

src/EchoHub.Server/Services/ChatService.cs

@@ -175,15 +175,15 @@ public class ChatService : IChatService
             }
         }
 
-        // Attempt to fetch link embed for URLs in the message
+        // Attempt to fetch link embeds for URLs in the message
-        EmbedDto? embed = null;
+        List<EmbedDto>? embeds = null;
         try
         {
-            embed = await _embedService.TryGetEmbedAsync(content);
+            embeds = await _embedService.TryGetEmbedsAsync(content);
         }
         catch (Exception ex)
         {
-            _logger.LogWarning(ex, "Failed to fetch link embed for message in '{Channel}'", channelName);
+            _logger.LogWarning(ex, "Failed to fetch link embeds for message in '{Channel}'", channelName);
         }
 
         var message = new Message
@@ -195,7 +195,7 @@ public class ChatService : IChatService
             ChannelId = channel.Id,
             SenderUserId = userId,
             SenderUsername = username,
-            EmbedJson = embed is not null ? JsonSerializer.Serialize(embed) : null,
+            EmbedJson = embeds is not null ? JsonSerializer.Serialize(embeds) : null,
         };
 
         db.Messages.Add(message);
@@ -211,7 +211,7 @@ public class ChatService : IChatService
             null,
             null,
             message.SentAt,
-            embed);
+            embeds);
 
         await BroadcastToAllAsync(b => b.SendMessageToChannelAsync(channelName, messageDto));
 
@@ -418,10 +418,10 @@ public class ChatService : IChatService
 
         return raw.Select(x =>
         {
-            EmbedDto? embed = null;
+            List<EmbedDto>? embeds = null;
             if (x.m.EmbedJson is not null)
             {
-                try { embed = JsonSerializer.Deserialize<EmbedDto>(x.m.EmbedJson); }
+                try { embeds = JsonSerializer.Deserialize<List<EmbedDto>>(x.m.EmbedJson); }
                 catch { /* ignore malformed JSON */ }
             }
 
@@ -435,7 +435,7 @@ public class ChatService : IChatService
                 x.m.AttachmentUrl,
                 x.m.AttachmentFileName,
                 x.m.SentAt,
-                embed);
+                embeds);
         }).ToList();
     }
 }

src/EchoHub.Server/Services/LinkEmbedService.cs

@@ -24,108 +24,119 @@ public partial class LinkEmbedService
     }
 
     /// <summary>
-    /// Detect the first URL in message content and attempt to fetch OG embed data.
+    /// Detect all URLs in message content and attempt to fetch OG embed data for each.
-    /// Returns null if no URL found, fetch fails, or no useful OG data.
+    /// Returns null if no URLs found or all fetches fail.
     /// Never throws — all errors are caught internally.
     /// </summary>
-    public async Task<EmbedDto?> TryGetEmbedAsync(string content)
+    public async Task<List<EmbedDto>?> TryGetEmbedsAsync(string content)
     {
-        try
+        var urls = ExtractUrls(content);
-        {
+        if (urls.Count == 0)
-            var url = ExtractFirstUrl(content);
-            if (url is null)
-                return null;
-
-            if (!Uri.TryCreate(url, UriKind.Absolute, out var uri))
-                return null;
-
-            if (uri.Scheme is not ("http" or "https"))
-                return null;
-
-            if (IsPrivateHost(uri))
-                return null;
-
-            using var cts = new CancellationTokenSource(
-                TimeSpan.FromSeconds(HubConstants.EmbedFetchTimeoutSeconds));
-
-            var client = _httpClientFactory.CreateClient("OgFetch");
-
-            using var request = new HttpRequestMessage(HttpMethod.Get, uri);
-            using var response = await client.SendAsync(request,
-                HttpCompletionOption.ResponseHeadersRead, cts.Token);
-
-            if (!response.IsSuccessStatusCode)
-                return null;
-
-            var contentType = response.Content.Headers.ContentType?.MediaType;
-            if (contentType is null || !contentType.StartsWith("text/html", StringComparison.OrdinalIgnoreCase))
-                return null;
-
-            var html = await ReadLimitedAsync(response, HubConstants.EmbedMaxHtmlBytes, cts.Token);
-            if (string.IsNullOrWhiteSpace(html))
-                return null;
-
-            var ogTags = ParseOgTags(html);
-
-            // Try og:title, fallback to <title> tag
-            var title = ogTags.GetValueOrDefault("title");
-            if (string.IsNullOrWhiteSpace(title))
-            {
-                var titleMatch = TitleTagRegex().Match(html);
-                if (titleMatch.Success)
-                    title = WebUtility.HtmlDecode(titleMatch.Groups[1].Value.Trim());
-            }
-
-            // If no title at all, nothing useful to show
-            if (string.IsNullOrWhiteSpace(title))
-                return null;
-
-            var siteName = ogTags.GetValueOrDefault("site_name");
-            var description = ogTags.GetValueOrDefault("description");
-
-            // Truncate description
-            if (description is not null && description.Length > HubConstants.EmbedMaxDescriptionLength)
-                description = description[..(HubConstants.EmbedMaxDescriptionLength - 3)] + "...";
-
-            // HTML decode text fields
-            title = WebUtility.HtmlDecode(title);
-            siteName = siteName is not null ? WebUtility.HtmlDecode(siteName) : null;
-            description = description is not null ? WebUtility.HtmlDecode(description) : null;
-
-            // Attempt to fetch OG image thumbnail
-            string? imageAscii = null;
-            var imageUrl = ogTags.GetValueOrDefault("image");
-            if (!string.IsNullOrWhiteSpace(imageUrl))
-            {
-                imageAscii = await FetchImageThumbnailAsync(imageUrl, uri, cts.Token);
-            }
-
-            return new EmbedDto(siteName, title, description, imageAscii, url);
-        }
-        catch (OperationCanceledException)
-        {
-            _logger.LogDebug("Embed fetch timed out for message content");
             return null;
-        }
+
-        catch (Exception ex)
+        var embeds = new List<EmbedDto>();
+
+        foreach (var url in urls)
         {
-            _logger.LogDebug(ex, "Failed to fetch embed");
+            try
-            return null;
+            {
+                var embed = await FetchEmbedForUrlAsync(url);
+                if (embed is not null)
+                    embeds.Add(embed);
+            }
+            catch (Exception ex)
+            {
+                _logger.LogDebug(ex, "Failed to fetch embed for {Url}", url);
+            }
         }
+
+        return embeds.Count > 0 ? embeds : null;
     }
 
-    private static string? ExtractFirstUrl(string content)
+    private async Task<EmbedDto?> FetchEmbedForUrlAsync(string url)
     {
-        var match = UrlRegex().Match(content);
+        if (!Uri.TryCreate(url, UriKind.Absolute, out var uri))
-        if (!match.Success)
             return null;
 
-        var url = match.Value;
+        if (uri.Scheme is not ("http" or "https"))
+            return null;
 
-        // Strip trailing punctuation that's likely not part of the URL
+        if (IsPrivateHost(uri))
-        url = url.TrimEnd('.', ',', '!', '?', ')', ']', ';', ':');
+            return null;
 
-        return url;
+        using var cts = new CancellationTokenSource(
+            TimeSpan.FromSeconds(HubConstants.EmbedFetchTimeoutSeconds));
+
+        var client = _httpClientFactory.CreateClient("OgFetch");
+
+        using var request = new HttpRequestMessage(HttpMethod.Get, uri);
+        using var response = await client.SendAsync(request,
+            HttpCompletionOption.ResponseHeadersRead, cts.Token);
+
+        if (!response.IsSuccessStatusCode)
+            return null;
+
+        var contentType = response.Content.Headers.ContentType?.MediaType;
+        if (contentType is null || !contentType.StartsWith("text/html", StringComparison.OrdinalIgnoreCase))
+            return null;
+
+        var html = await ReadLimitedAsync(response, HubConstants.EmbedMaxHtmlBytes, cts.Token);
+        if (string.IsNullOrWhiteSpace(html))
+            return null;
+
+        var ogTags = ParseOgTags(html);
+
+        // Try og:title, fallback to <title> tag
+        var title = ogTags.GetValueOrDefault("title");
+        if (string.IsNullOrWhiteSpace(title))
+        {
+            var titleMatch = TitleTagRegex().Match(html);
+            if (titleMatch.Success)
+                title = WebUtility.HtmlDecode(titleMatch.Groups[1].Value.Trim());
+        }
+
+        // If no title at all, nothing useful to show
+        if (string.IsNullOrWhiteSpace(title))
+            return null;
+
+        var siteName = ogTags.GetValueOrDefault("site_name");
+        var description = ogTags.GetValueOrDefault("description");
+
+        // Truncate very long descriptions but keep a generous limit
+        if (description is not null && description.Length > HubConstants.EmbedMaxDescriptionLength)
+            description = description[..(HubConstants.EmbedMaxDescriptionLength - 3)] + "...";
+
+        // HTML decode text fields
+        title = WebUtility.HtmlDecode(title);
+        siteName = siteName is not null ? WebUtility.HtmlDecode(siteName) : null;
+        description = description is not null ? WebUtility.HtmlDecode(description) : null;
+
+        // Attempt to fetch OG image as small icon
+        string? imageAscii = null;
+        var imageUrl = ogTags.GetValueOrDefault("image");
+        if (!string.IsNullOrWhiteSpace(imageUrl))
+        {
+            imageAscii = await FetchImageThumbnailAsync(imageUrl, uri, cts.Token);
+        }
+
+        return new EmbedDto(siteName, title, description, imageAscii, url);
+    }
+
+    private static List<string> ExtractUrls(string content)
+    {
+        var urls = new List<string>();
+
+        foreach (Match match in UrlRegex().Matches(content))
+        {
+            var url = match.Value.TrimEnd('.', ',', '!', '?', ')', ']', ';', ':');
+            if (!urls.Contains(url))
+                urls.Add(url);
+
+            if (urls.Count >= HubConstants.EmbedMaxUrlsPerMessage)
+                break;
+        }
+
+        return urls;
     }
 
     private static bool IsPrivateHost(Uri uri)
@@ -220,8 +231,8 @@ public partial class LinkEmbedService
             memoryStream.Position = 0;
 
             return _asciiService.ConvertToAscii(memoryStream,
-                HubConstants.EmbedThumbnailWidth,
+                HubConstants.EmbedIconWidth,
-                HubConstants.EmbedThumbnailHeight);
+                HubConstants.EmbedIconHeight);
         }
         catch (Exception ex)
         {

src/EchoHub.Server/Setup/DataMigrationService.cs

@@ -1,5 +1,6 @@
 using System.Text.RegularExpressions;
 using EchoHub.Core.Constants;
+using EchoHub.Core.DTOs;
 using EchoHub.Server.Data;
 using Microsoft.EntityFrameworkCore;
 
@@ -16,6 +17,7 @@ public static partial class DataMigrationService
 
         await EnsureDefaultChannelsPublicAsync(db, logger);
         await MigrateAnsiMessagesAsync(db, logger);
+        await MigrateEmbedJsonToArrayAsync(db, logger);
     }
 
     /// <summary>
@@ -91,4 +93,47 @@ public static partial class DataMigrationService
 
     [GeneratedRegex(@"\x1b\[(?:(0)|(?:(38;2|48;2);(\d{1,3});(\d{1,3});(\d{1,3})))m")]
     private static partial Regex AnsiColorRegex();
+
+    /// <summary>
+    /// Migrate old single-object EmbedJson ("{...}") to array format ("[{...}]").
+    /// </summary>
+    private static async Task MigrateEmbedJsonToArrayAsync(EchoHubDbContext db, ILogger logger)
+    {
+        var messages = await db.Messages
+            .Where(m => m.EmbedJson != null)
+            .ToListAsync();
+
+        var toMigrate = messages
+            .Where(m => m.EmbedJson!.TrimStart().StartsWith('{'))
+            .ToList();
+
+        if (toMigrate.Count == 0)
+            return;
+
+        logger.LogInformation("Found {Count} messages with legacy single-embed JSON. Migrating to array format...", toMigrate.Count);
+
+        var modified = 0;
+        foreach (var message in toMigrate)
+        {
+            try
+            {
+                var single = System.Text.Json.JsonSerializer.Deserialize<EmbedDto>(message.EmbedJson!);
+                if (single is not null)
+                {
+                    message.EmbedJson = System.Text.Json.JsonSerializer.Serialize(new[] { single });
+                    modified++;
+                }
+            }
+            catch
+            {
+                // Skip malformed JSON
+            }
+        }
+
+        if (modified > 0)
+        {
+            await db.SaveChangesAsync();
+            logger.LogInformation("Migrated {Count} embed records from single-object to array format.", modified);
+        }
+    }
 }