feat: Add support for message attachments

- Introduced Attachment model to handle file attachments associated with messages.
- Updated ModerationController to manage message deletions and attachment cleanup.
- Enhanced ChatService to include attachments in message retrieval.
- Implemented migration for legacy single-attachment messages to the new Attachments model.
- Added unit tests for attachment handling in message formatting and parsing.
- Updated database context and migrations to support new Attachments table.

src/EchoHub.Client/AppOrchestrator.cs

@@ -33,6 +33,7 @@ public sealed class AppOrchestrator : IDisposable
     private readonly Dictionary<string, List<UserPresenceDto>> _channelUsers = new(StringComparer.OrdinalIgnoreCase);
     private readonly Lock _channelUsersLock = new();
     private readonly HashSet<string> _channelsLoadingMore = new(StringComparer.OrdinalIgnoreCase);
+    private readonly List<string> _stagedAttachments = [];
 
     private ClientConfig _config;
     private readonly UserSession _session = new();
@@ -91,6 +92,7 @@ public sealed class AppOrchestrator : IDisposable
         _mainWindow.OnAudioPlayRequested += HandleAudioPlayRequested;
         _mainWindow.OnFileDownloadRequested += HandleFileDownloadRequested;
         _mainWindow.OnImageSaveRequested += HandleImageSaveRequested;
+        _mainWindow.OnDeleteMessageRequested += HandleDeleteMessageRequested;
         _mainWindow.OnCheckForUpdatesRequested += HandleCheckForUpdatesRequested;
         _mainWindow.OnRollbackRequested += HandleRollbackRequested;
         _mainWindow.OnUserProfileRequested += HandleViewProfile;
@@ -113,6 +115,8 @@ public sealed class AppOrchestrator : IDisposable
         _commandHandler.OnOpenServers += HandleCmdOpenServers;
         _commandHandler.OnJoinChannel += HandleCmdJoinChannel;
         _commandHandler.OnChangeRoomPassword += HandleCmdChangeRoomPassword;
+        _commandHandler.OnClearAttachments += HandleCmdClearAttachments;
+        _commandHandler.OnSetDownloadPath += HandleCmdSetDownloadPath;
         _commandHandler.OnLeaveChannel += HandleCmdLeaveChannel;
         _commandHandler.OnSetTopic += HandleCmdSetTopic;
         _commandHandler.OnListUsers += HandleCmdListUsers;
@@ -162,85 +166,107 @@ public sealed class AppOrchestrator : IDisposable
         return Task.CompletedTask;
     }
 
-    private async Task HandleCmdSendFile(string target, string? size)
+    private Task HandleCmdSendFile(string target, string? size)
     {
-        if (!_conn.IsAuthenticated || !_conn.IsConnected) return;
+        if (!_conn.IsAuthenticated || !_conn.IsConnected) return Task.CompletedTask;
 
         var channel = _mainWindow.CurrentChannel;
-        if (string.IsNullOrEmpty(channel)) return;
+        if (string.IsNullOrEmpty(channel)) return Task.CompletedTask;
 
-        try
+        // A URL image is sent immediately as its own message (it can't be staged/encrypted).
+        if (Uri.TryCreate(target, UriKind.Absolute, out var uri)
+            && (uri.Scheme == "http" || uri.Scheme == "https"))
         {
-            var hasRoomKey = _conn.RoomKeys.TryGetKey(channel, out var roomKey);
+            if (_conn.RoomKeys.HasKey(channel))
+            {
+                InvokeUI(() => _mainWindow.ShowError(
+                    "Sending by URL isn't available in encrypted channels — download the file and /send it instead."));
+                return Task.CompletedTask;
+            }
 
-            if (Uri.TryCreate(target, UriKind.Absolute, out var uri)
-                && (uri.Scheme == "http" || uri.Scheme == "https"))
-            {
-                if (hasRoomKey)
-                {
-                    InvokeUI(() => _mainWindow.ShowError(
-                        "Sending by URL isn't available in encrypted channels — download the file and /send it instead."));
-                    return;
-                }
-
-                await _conn.Api!.SendUrlAsync(channel, target, size);
-            }
-            else if (hasRoomKey)
-            {
-                await UploadEncryptedFileAsync(channel, target, size, roomKey);
-            }
-            else
-            {
-                await using var stream = File.OpenRead(target);
-                var fileName = Path.GetFileName(target);
-                await _conn.Api!.UploadFileAsync(channel, stream, fileName, size);
-            }
+            RunAsync(async () => await _conn.Api!.SendUrlAsync(channel, target, size), "Send failed");
+            return Task.CompletedTask;
         }
-        catch (Exception ex)
+
+        // Local files are staged; the next Enter sends them with the typed caption as one message.
+        if (_stagedAttachments.Count >= HubConstants.MaxAttachmentsPerMessage)
         {
-            Log.Error(ex, "File send failed for {Target}", target);
-            InvokeUI(() => _mainWindow.ShowError($"Send failed: {ex.Message}"));
+            InvokeUI(() => _mainWindow.ShowError($"You can attach at most {HubConstants.MaxAttachmentsPerMessage} files per message."));
+            return Task.CompletedTask;
         }
+
+        _stagedAttachments.Add(target);
+        InvokeUI(() => _mainWindow.SetStagedAttachments(_stagedAttachments.Select(Path.GetFileName).OfType<string>().ToList()));
+        return Task.CompletedTask;
+    }
+
+    private Task HandleCmdClearAttachments()
+    {
+        _stagedAttachments.Clear();
+        InvokeUI(() => _mainWindow.SetStagedAttachments([]));
+        return Task.CompletedTask;
     }
 
     /// <summary>
-    /// Upload into an end-to-end encrypted channel: the blob is encrypted with the room
-    /// key before it leaves this machine, and for images the ASCII preview is rendered
-    /// locally and sent room-encrypted — the server never sees image or file contents.
+    /// Sends one message with the given caption plus all staged files as attachments, then
+    /// clears the staging tray. In encrypted channels each file is room-encrypted (blob +
+    /// ASCII preview) client-side before upload; the caption is room-encrypted too.
     /// </summary>
-    private async Task UploadEncryptedFileAsync(string channel, string path, string? size, byte[] roomKey)
+    private void SendStagedMessage(string channel, string content)
+    {
+        var staged = _stagedAttachments.ToList();
+        _stagedAttachments.Clear();
+        InvokeUI(() => _mainWindow.SetStagedAttachments([]));
+
+        var hasRoomKey = _conn.RoomKeys.TryGetKey(channel, out var roomKey);
+
+        RunAsync(async () =>
+        {
+            var outgoing = new List<OutgoingAttachment>();
+            foreach (var path in staged)
+                outgoing.Add(await BuildOutgoingAttachmentAsync(path, hasRoomKey ? roomKey : null));
+
+            var wireContent = hasRoomKey && !string.IsNullOrEmpty(content)
+                ? RoomCrypto.EncryptText(content, roomKey)
+                : content;
+
+            await _conn.Api!.SendMessageWithAttachmentsAsync(channel, wireContent, outgoing);
+        }, "Send failed");
+    }
+
+    /// <summary>
+    /// Reads a staged file into an <see cref="OutgoingAttachment"/>. For encrypted channels the
+    /// blob is AES-GCM encrypted, its kind is declared, and the image ASCII preview is rendered
+    /// locally and room-encrypted — so the server never sees the file or image contents.
+    /// </summary>
+    private static async Task<OutgoingAttachment> BuildOutgoingAttachmentAsync(string path, byte[]? roomKey)
     {
         var fileName = Path.GetFileName(path);
-        var bytes = await File.ReadAllBytesAsync(path);
 
-        string declaredType;
-        string plainContent;
+        if (roomKey is null)
+            return new OutgoingAttachment(File.OpenRead(path), fileName);
+
+        var bytes = await File.ReadAllBytesAsync(path);
+        string declaredKind;
+        string? preview = null;
+
         using (var ms = new MemoryStream(bytes))
         {
             if (FileValidationHelper.IsValidImage(ms))
             {
-                declaredType = "image";
-                var (w, h) = ImageToAsciiService.GetDimensions(size);
+                declaredKind = "image";
+                var (w, h) = ImageToAsciiService.GetDimensions(null);
                 ms.Position = 0;
-                plainContent = new ImageToAsciiService().ConvertToAscii(ms, w, h);
-            }
-            else if (FileValidationHelper.IsAudioFile(fileName))
-            {
-                declaredType = "audio";
-                plainContent = fileName;
+                preview = RoomCrypto.EncryptText(new ImageToAsciiService().ConvertToAscii(ms, w, h), roomKey);
             }
             else
             {
-                declaredType = "file";
-                plainContent = fileName;
+                declaredKind = FileValidationHelper.IsAudioFile(fileName) ? "audio" : "file";
             }
         }
 
-        var encryptedContent = RoomCrypto.EncryptText(plainContent, roomKey);
         var encryptedBlob = RoomCrypto.EncryptBytes(bytes, roomKey);
-
-        await using var blobStream = new MemoryStream(encryptedBlob);
-        await _conn.Api!.UploadFileAsync(channel, blobStream, fileName, size, declaredType, encryptedContent);
+        return new OutgoingAttachment(new MemoryStream(encryptedBlob), fileName, declaredKind, preview);
     }
 
     private async Task HandleCmdSetAvatar(string target)
@@ -893,11 +919,28 @@ public sealed class AppOrchestrator : IDisposable
             return;
         }
 
+        // Staged files → one message with the typed caption plus those attachments.
+        if (_stagedAttachments.Count > 0)
+        {
+            SendStagedMessage(channelName, content);
+            return;
+        }
+
         RunAsync(
             async () => await _conn.SendMessageAsync(channelName, content),
             "Send failed");
     }
 
+    private void HandleDeleteMessageRequested(Guid messageId)
+    {
+        if (!_conn.IsAuthenticated) return;
+
+        // The server enforces the hierarchy rule (own message, or Mod+ over a strictly
+        // lower role) and broadcasts the deletion; the local list updates on that event.
+        RunAsync(async () => await _conn.Api!.DeleteMessageAsync(messageId),
+            "Failed to delete message");
+    }
+
     private void HandleChannelSelected(string channelName)
     {
         if (!_conn.IsConnected) return;
@@ -1319,20 +1362,46 @@ public sealed class AppOrchestrator : IDisposable
             InvokeUI(() => _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, $"Downloading {fileName}..."));
             var tempPath = await DownloadAttachmentAsync(attachmentUrl, fileName);
 
-            var downloads = Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.UserProfile), "Downloads");
-            Directory.CreateDirectory(downloads);
-
-            var stem = Path.GetFileNameWithoutExtension(fileName);
-            var ext = Path.GetExtension(fileName);
-            var destination = Path.Combine(downloads, fileName);
-            for (var i = 1; File.Exists(destination); i++)
-                destination = Path.Combine(downloads, $"{stem} ({i}){ext}");
-
+            var destination = DedupPath(GetDownloadDir(), fileName);
             File.Move(tempPath, destination);
             InvokeUI(() => _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, $"Image saved to: {destination}"));
         }, "Failed to save image");
     }
 
+    /// <summary>
+    /// Resolves the folder downloads are written to: the user's configured
+    /// <see cref="ClientConfig.DownloadPath"/> if set, otherwise the OS Downloads folder.
+    /// Falls back to the temp folder if neither can be created.
+    /// </summary>
+    private string GetDownloadDir()
+    {
+        var dir = _config.DownloadPath;
+        if (string.IsNullOrWhiteSpace(dir))
+            dir = Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.UserProfile), "Downloads");
+
+        try
+        {
+            Directory.CreateDirectory(dir);
+            return dir;
+        }
+        catch (Exception ex)
+        {
+            Log.Warning(ex, "Download folder {Dir} is not usable; falling back to temp", dir);
+            return Path.GetTempPath();
+        }
+    }
+
+    /// <summary>Appends " (n)" before the extension until the path doesn't collide with an existing file.</summary>
+    private static string DedupPath(string dir, string fileName)
+    {
+        var stem = Path.GetFileNameWithoutExtension(fileName);
+        var ext = Path.GetExtension(fileName);
+        var dest = Path.Combine(dir, fileName);
+        for (var i = 1; File.Exists(dest); i++)
+            dest = Path.Combine(dir, $"{stem} ({i}){ext}");
+        return dest;
+    }
+
     /// <summary>
     /// File extensions considered safe to open with the system default application.
     /// Everything else is downloaded only — never auto-opened via UseShellExecute.
@@ -1352,27 +1421,81 @@ public sealed class AppOrchestrator : IDisposable
             InvokeUI(() => _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, $"Downloading {fileName}..."));
             var tempPath = await DownloadAttachmentAsync(attachmentUrl, fileName);
 
-            var ext = Path.GetExtension(fileName);
-            if (SafeOpenExtensions.Contains(ext))
+            var destination = DedupPath(GetDownloadDir(), fileName);
+            File.Move(tempPath, destination);
+            InvokeUI(() => _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, $"Saved to: {destination}"));
+
+            if (SafeOpenExtensions.Contains(Path.GetExtension(fileName)))
             {
                 try
                 {
-                    var psi = new System.Diagnostics.ProcessStartInfo(tempPath) { UseShellExecute = true };
+                    var psi = new System.Diagnostics.ProcessStartInfo(destination) { UseShellExecute = true };
                     System.Diagnostics.Process.Start(psi);
                 }
                 catch (Exception ex)
                 {
-                    Log.Warning(ex, "Failed to open file with default app: {Path}", tempPath);
-                    InvokeUI(() => _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, $"Downloaded to: {tempPath}"));
+                    Log.Warning(ex, "Failed to open file with default app: {Path}", destination);
                 }
             }
-            else
-            {
-                InvokeUI(() => _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, $"Downloaded to: {tempPath}"));
-            }
         }, "Failed to download file");
     }
 
+    /// <summary>
+    /// Sets the download folder. With no argument, opens the OS-native folder picker; if that
+    /// isn't available (headless, missing tool), tells the user to pass a path instead. With an
+    /// argument, sets that path directly (the fallback for machines with no native picker).
+    /// </summary>
+    private Task HandleCmdSetDownloadPath(string args)
+    {
+        var current = _config.DownloadPath ?? GetDownloadDir();
+
+        if (!string.IsNullOrWhiteSpace(args))
+        {
+            SetDownloadPath(args.Trim());
+            return Task.CompletedTask;
+        }
+
+        RunAsync(async () =>
+        {
+            var result = await NativeFolderPicker.PickFolderAsync(current);
+            InvokeUI(() =>
+            {
+                switch (result.Outcome)
+                {
+                    case PickerOutcome.Chosen when result.Path is not null:
+                        SetDownloadPath(result.Path);
+                        break;
+                    case PickerOutcome.Cancelled:
+                        _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, "Download folder unchanged.");
+                        break;
+                    case PickerOutcome.Unavailable:
+                        _messageManager.AddSystemMessage(_mainWindow.CurrentChannel,
+                            $"No native folder picker here. Current download folder: {current}\nSet one with: /downloadpath <path>");
+                        break;
+                }
+            });
+        }, "Failed to open folder picker");
+
+        return Task.CompletedTask;
+    }
+
+    private void SetDownloadPath(string path)
+    {
+        try
+        {
+            Directory.CreateDirectory(path);
+        }
+        catch (Exception ex)
+        {
+            InvokeUI(() => _mainWindow.ShowError($"Can't use that folder: {ex.Message}"));
+            return;
+        }
+
+        _config.DownloadPath = path;
+        ConfigManager.Save(_config);
+        InvokeUI(() => _messageManager.AddSystemMessage(_mainWindow.CurrentChannel, $"Download folder set to: {path}"));
+    }
+
     private void HandleCheckForUpdatesRequested()
     {
         RunAsync(_updateService.CheckNowAsync, "Failed to check for updates");

src/EchoHub.Client/Commands/CommandHandler.cs

@@ -15,6 +15,8 @@ public class CommandHandler
     public event Func<Task>? OnOpenServers;
     public event Func<string, string?, Task>? OnJoinChannel;
     public event Func<string, string, Task>? OnChangeRoomPassword;
+    public event Func<Task>? OnClearAttachments;
+    public event Func<string, Task>? OnSetDownloadPath;
     public event Func<Task>? OnLeaveChannel;
     public event Func<string, Task>? OnSetTopic;
     public event Func<Task>? OnListUsers;
@@ -48,6 +50,8 @@ public class CommandHandler
             "color" => await HandleColor(args),
             "theme" => await HandleTheme(args),
             "send" => await HandleSend(args),
+            "clear" => await HandleClear(),
+            "downloadpath" or "downloads" => await HandleDownloadPath(args),
             "profile" => await HandleProfile(args),
             "avatar" => await HandleAvatar(args),
             "servers" => await HandleServers(),
@@ -165,6 +169,21 @@ public class CommandHandler
         return new CommandResult(true, $"Uploading: {Path.GetFileName(target)}...");
     }
 
+    private async Task<CommandResult> HandleClear()
+    {
+        if (OnClearAttachments is not null)
+            await OnClearAttachments();
+        return new CommandResult(true, "Cleared staged attachments.");
+    }
+
+    private async Task<CommandResult> HandleDownloadPath(string args)
+    {
+        // No argument → open the native folder picker; an argument sets the path directly.
+        if (OnSetDownloadPath is not null)
+            await OnSetDownloadPath(args.Trim());
+        return new CommandResult(true);
+    }
+
     private async Task<CommandResult> HandleProfile(string args)
     {
         var username = string.IsNullOrWhiteSpace(args) ? null : args.Trim();
@@ -358,7 +377,11 @@ public class CommandHandler
               /nick <name>                         - Set display name
               /color <#hex>                        - Set nickname color
               /theme <name>                        - Switch theme
-              /send <filepath or URL> [-s|-m|-l]      - Send file/image/audio (size flag for images)
+              /send <filepath> [-s|-m|-l]          - Stage a file to attach (Enter sends with your text)
+              /send <URL> [-s|-m|-l]               - Send an image URL immediately
+              /clear                               - Drop all staged attachments
+            (Tip: copy a file and press Ctrl+V, or drag a file onto the window, to attach it.)
+              /downloadpath [path]                 - Set download folder (no path = native folder picker)
               /avatar <URL or filepath>             - Set your avatar
               /profile [username]                   - View a profile
               /servers                             - Open saved servers

src/EchoHub.Client/Config/ClientConfig.cs

@@ -6,6 +6,12 @@ public class ClientConfig
     public AccountPreset DefaultPreset { get; set; } = new();
     public string ActiveTheme { get; set; } = "Default";
     public NotificationConfig Notifications { get; set; } = new();
+
+    /// <summary>
+    /// Folder where downloaded attachments and saved images are written. When null, the
+    /// OS Downloads folder is used. Set via the native folder picker or <c>/downloadpath</c>.
+    /// </summary>
+    public string? DownloadPath { get; set; }
 }
 
 public class NotificationConfig

src/EchoHub.Client/Services/ApiClient.cs

@@ -185,25 +185,35 @@ public sealed class ApiClient : IDisposable
         return result?.AvatarAscii;
     }
 
-    public async Task<MessageDto?> UploadFileAsync(string channelName, Stream fileStream, string fileName, string? size = null,
-        string? declaredType = null, string? encryptedContent = null)
+    /// <summary>
+    /// Sends one message with optional text and one or more file attachments.
+    /// For end-to-end encrypted channels each attachment carries a declared kind and a
+    /// room-encrypted preview (empty when none); the caption is likewise room-encrypted.
+    /// </summary>
+    public async Task<MessageDto?> SendMessageWithAttachmentsAsync(
+        string channelName, string content, IReadOnlyList<OutgoingAttachment> attachments, string? size = null)
     {
         EnsureAuthenticated();
-        using var content = new MultipartFormDataContent();
-        using var streamContent = new StreamContent(fileStream);
-        streamContent.Headers.ContentType = new MediaTypeHeaderValue(GetContentType(fileName));
-        content.Add(streamContent, "file", fileName);
+        using var form = new MultipartFormDataContent { { new StringContent(content), "content" } };
 
-        // E2E channels: the blob is ciphertext, so the client declares the type and
-        // supplies the room-encrypted message content the server can't produce.
-        if (declaredType is not null)
-            content.Add(new StringContent(declaredType), "type");
-        if (encryptedContent is not null)
-            content.Add(new StringContent(encryptedContent), "content");
+        foreach (var att in attachments)
+        {
+            var streamContent = new StreamContent(att.Stream);
+            streamContent.Headers.ContentType = new MediaTypeHeaderValue(GetContentType(att.FileName));
+            form.Add(streamContent, "file", att.FileName);
+
+            // Encrypted channels: one kind + preview per file, in the same order, to keep
+            // the server's index alignment (empty preview string for non-images).
+            if (att.DeclaredKind is not null)
+            {
+                form.Add(new StringContent(att.DeclaredKind), "kind");
+                form.Add(new StringContent(att.EncryptedPreview ?? string.Empty), "preview");
+            }
+        }
 
         var sizeQuery = size is not null ? $"?size={size}" : "";
         using var response = await AuthenticatedRequestAsync(() =>
-            _http.PostAsync($"/api/channels/{Uri.EscapeDataString(channelName)}/upload{sizeQuery}", content));
+            _http.PostAsync($"/api/channels/{Uri.EscapeDataString(channelName)}/messages{sizeQuery}", form));
         await EnsureSuccessAsync(response);
         return await response.Content.ReadFromJsonAsync<MessageDto>();
     }

src/EchoHub.Client/Services/ClipboardFiles.cs

@@ -0,0 +1,154 @@
+using System.Diagnostics;
+using System.Runtime.InteropServices;
+using System.Runtime.Versioning;
+using System.Text;
+using Serilog;
+
+namespace EchoHub.Client.Services;
+
+/// <summary>
+/// Reads file paths that live on the OS clipboard as a *file list* (e.g. after copying a file in
+/// Explorer/Finder/Nautilus), which terminals do not paste as text. Lets Ctrl+V attach a copied
+/// file directly instead of requiring the user to paste a raw path.
+/// </summary>
+public static class ClipboardFiles
+{
+    public static bool TryGetFiles(out List<string> files)
+    {
+        files = [];
+        try
+        {
+            if (OperatingSystem.IsWindows())
+                return TryGetWindows(out files);
+            if (OperatingSystem.IsLinux())
+                return TryGetLinux(out files);
+        }
+        catch (Exception ex)
+        {
+            Log.Warning(ex, "Reading files from the clipboard failed");
+        }
+
+        // macOS and everything else: no file-list clipboard support (text paste still works).
+        return false;
+    }
+
+    // ── Windows: CF_HDROP via the Win32 clipboard ────────────────────────────
+
+    private const uint CfHdrop = 15;
+
+    [SupportedOSPlatform("windows")]
+    private static bool TryGetWindows(out List<string> files)
+    {
+        files = [];
+        if (!IsClipboardFormatAvailable(CfHdrop))
+            return false;
+
+        // The clipboard may briefly be held by another process; a few quick retries cover that.
+        var opened = false;
+        for (var attempt = 0; attempt < 5 && !opened; attempt++)
+            opened = OpenClipboard(IntPtr.Zero);
+        if (!opened)
+            return false;
+
+        try
+        {
+            var hDrop = GetClipboardData(CfHdrop);
+            if (hDrop == IntPtr.Zero)
+                return false;
+
+            var count = DragQueryFileW(hDrop, 0xFFFFFFFF, null, 0);
+            for (uint i = 0; i < count; i++)
+            {
+                var len = DragQueryFileW(hDrop, i, null, 0);
+                if (len == 0)
+                    continue;
+
+                var sb = new StringBuilder((int)len + 1);
+                DragQueryFileW(hDrop, i, sb, (uint)sb.Capacity);
+                var path = sb.ToString();
+                if (File.Exists(path))
+                    files.Add(path);
+            }
+
+            return files.Count > 0;
+        }
+        finally
+        {
+            CloseClipboard();
+        }
+    }
+
+    [DllImport("user32.dll", SetLastError = true)]
+    [return: MarshalAs(UnmanagedType.Bool)]
+    private static extern bool OpenClipboard(IntPtr hWndNewOwner);
+
+    [DllImport("user32.dll", SetLastError = true)]
+    [return: MarshalAs(UnmanagedType.Bool)]
+    private static extern bool CloseClipboard();
+
+    [DllImport("user32.dll", SetLastError = true)]
+    [return: MarshalAs(UnmanagedType.Bool)]
+    private static extern bool IsClipboardFormatAvailable(uint format);
+
+    [DllImport("user32.dll", SetLastError = true)]
+    private static extern IntPtr GetClipboardData(uint uFormat);
+
+    [DllImport("shell32.dll", CharSet = CharSet.Unicode)]
+    private static extern uint DragQueryFileW(IntPtr hDrop, uint iFile, StringBuilder? lpszFile, uint cch);
+
+    // ── Linux: text/uri-list from the clipboard via xclip or wl-paste ─────────
+
+    [SupportedOSPlatform("linux")]
+    private static bool TryGetLinux(out List<string> files)
+    {
+        files = [];
+
+        var output = RunForOutput("wl-paste", ["--type", "text/uri-list", "--no-newline"])
+            ?? RunForOutput("xclip", ["-selection", "clipboard", "-t", "text/uri-list", "-o"]);
+        if (string.IsNullOrWhiteSpace(output))
+            return false;
+
+        foreach (var line in output.Split('\n', StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries))
+        {
+            if (!line.StartsWith("file://", StringComparison.Ordinal))
+                continue;
+            try
+            {
+                var path = new Uri(line).LocalPath;
+                if (File.Exists(path))
+                    files.Add(path);
+            }
+            catch (UriFormatException) { /* skip malformed entry */ }
+        }
+
+        return files.Count > 0;
+    }
+
+    private static string? RunForOutput(string fileName, IEnumerable<string> args)
+    {
+        var psi = new ProcessStartInfo(fileName)
+        {
+            RedirectStandardOutput = true,
+            RedirectStandardError = true,
+            UseShellExecute = false,
+            CreateNoWindow = true,
+        };
+        foreach (var arg in args)
+            psi.ArgumentList.Add(arg);
+
+        try
+        {
+            using var process = Process.Start(psi);
+            if (process is null)
+                return null;
+
+            var output = process.StandardOutput.ReadToEnd();
+            process.WaitForExit(2000);
+            return process.ExitCode == 0 ? output : null;
+        }
+        catch (Exception ex) when (ex is System.ComponentModel.Win32Exception or FileNotFoundException)
+        {
+            return null; // tool not installed
+        }
+    }
+}

src/EchoHub.Client/Services/EchoHubConnection.cs

@@ -207,28 +207,41 @@ public sealed class EchoHubConnection : IAsyncDisposable
     }
 
     /// <summary>
-    /// Strips the transport encryption, then the room layer for E2E channels.
-    /// Without the room key the content is replaced by a locked placeholder —
-    /// re-fetch history after unlocking to render it.
+    /// Strips the transport encryption, then the room layer for E2E channels, from the
+    /// message content and every attachment preview. Without the room key the content is
+    /// replaced by a locked placeholder — re-fetch history after unlocking to render it.
     /// </summary>
     private MessageDto DecryptMessage(MessageDto message)
     {
-        var content = _encryption.Decrypt(message.Content);
+        _roomKeys.TryGetKey(message.ChannelName, out var roomKey);
 
-        if (RoomCrypto.IsRoomCiphertext(content))
+        var content = DecryptField(message.Content, roomKey) ?? LockedMessagePlaceholder;
+
+        List<AttachmentDto>? attachments = null;
+        if (message.Attachments is { Count: > 0 })
         {
-            if (_roomKeys.TryGetKey(message.ChannelName, out var roomKey)
-                && RoomCrypto.TryDecryptText(content, roomKey, out var plaintext))
-            {
-                content = plaintext;
-            }
-            else
-            {
-                content = LockedMessagePlaceholder;
-            }
+            attachments = message.Attachments
+                .Select(a => a with { AsciiPreview = a.AsciiPreview is null ? null : DecryptField(a.AsciiPreview, roomKey) })
+                .ToList();
         }
 
-        return message with { Content = content };
+        return message with { Content = content, Attachments = attachments };
+    }
+
+    /// <summary>
+    /// Decrypts one field: strips transport encryption, then the room layer if it is room
+    /// ciphertext. Returns null when it is room ciphertext but the room key is missing/wrong.
+    /// </summary>
+    private string? DecryptField(string value, byte[]? roomKey)
+    {
+        var plain = _encryption.Decrypt(value);
+        if (!RoomCrypto.IsRoomCiphertext(plain))
+            return plain;
+
+        if (roomKey is not null && RoomCrypto.TryDecryptText(plain, roomKey, out var decrypted))
+            return decrypted;
+
+        return null;
     }
 
     public async ValueTask DisposeAsync()

src/EchoHub.Client/Services/NativeFolderPicker.cs

@@ -0,0 +1,141 @@
+using System.Diagnostics;
+using System.Runtime.InteropServices;
+using System.Text;
+using Serilog;
+
+namespace EchoHub.Client.Services;
+
+public enum PickerOutcome
+{
+    /// <summary>The user picked a folder (<see cref="FolderPickResult.Path"/> is set).</summary>
+    Chosen,
+
+    /// <summary>The native dialog ran but the user cancelled it.</summary>
+    Cancelled,
+
+    /// <summary>No native picker is available on this machine (headless, missing tool, etc.).</summary>
+    Unavailable,
+}
+
+public sealed record FolderPickResult(PickerOutcome Outcome, string? Path);
+
+/// <summary>
+/// Opens the OS-native folder chooser (Windows Explorer, macOS Finder, Linux GTK/KDE) by shelling
+/// out, so the TUI doesn't need a GUI toolkit reference. Returns <see cref="PickerOutcome.Unavailable"/>
+/// when no native dialog can run, so callers can fall back to a configured path.
+/// </summary>
+public static class NativeFolderPicker
+{
+    private const string Title = "Choose your EchoHub download folder";
+
+    public static async Task<FolderPickResult> PickFolderAsync(string? initialDir)
+    {
+        try
+        {
+            if (RuntimeInformation.IsOSPlatform(OSPlatform.Windows))
+                return await PickWindowsAsync(initialDir);
+            if (RuntimeInformation.IsOSPlatform(OSPlatform.OSX))
+                return await PickMacAsync();
+            if (RuntimeInformation.IsOSPlatform(OSPlatform.Linux))
+                return await PickLinuxAsync(initialDir);
+        }
+        catch (Exception ex)
+        {
+            Log.Warning(ex, "Native folder picker failed");
+        }
+
+        return new FolderPickResult(PickerOutcome.Unavailable, null);
+    }
+
+    private static async Task<FolderPickResult> PickWindowsAsync(string? initialDir)
+    {
+        var safeInit = (initialDir ?? string.Empty).Replace("'", "''");
+        var script = $$"""
+            Add-Type -AssemblyName System.Windows.Forms
+            $d = New-Object System.Windows.Forms.FolderBrowserDialog
+            $d.Description = '{{Title}}'
+            $d.ShowNewFolderButton = $true
+            $d.SelectedPath = '{{safeInit}}'
+            if ($d.ShowDialog() -eq [System.Windows.Forms.DialogResult]::OK) { [Console]::Out.Write($d.SelectedPath) }
+            """;
+
+        // -EncodedCommand avoids all quoting issues; FolderBrowserDialog needs an STA thread.
+        var encoded = Convert.ToBase64String(Encoding.Unicode.GetBytes(script));
+        var (started, _, stdout) = await RunAsync("powershell.exe",
+            ["-STA", "-NoProfile", "-NonInteractive", "-EncodedCommand", encoded]);
+
+        if (!started)
+            return new FolderPickResult(PickerOutcome.Unavailable, null);
+        return string.IsNullOrWhiteSpace(stdout)
+            ? new FolderPickResult(PickerOutcome.Cancelled, null)
+            : new FolderPickResult(PickerOutcome.Chosen, stdout);
+    }
+
+    private static async Task<FolderPickResult> PickMacAsync()
+    {
+        var (started, exit, stdout) = await RunAsync("osascript",
+            ["-e", $"POSIX path of (choose folder with prompt \"{Title}\")"]);
+
+        if (!started)
+            return new FolderPickResult(PickerOutcome.Unavailable, null);
+        return exit == 0 && !string.IsNullOrWhiteSpace(stdout)
+            ? new FolderPickResult(PickerOutcome.Chosen, stdout)
+            : new FolderPickResult(PickerOutcome.Cancelled, null);
+    }
+
+    private static async Task<FolderPickResult> PickLinuxAsync(string? initialDir)
+    {
+        // No graphical session → no native picker.
+        if (string.IsNullOrEmpty(Environment.GetEnvironmentVariable("DISPLAY"))
+            && string.IsNullOrEmpty(Environment.GetEnvironmentVariable("WAYLAND_DISPLAY")))
+            return new FolderPickResult(PickerOutcome.Unavailable, null);
+
+        var zenityArgs = new List<string> { "--file-selection", "--directory", $"--title={Title}" };
+        if (!string.IsNullOrWhiteSpace(initialDir))
+            zenityArgs.Add($"--filename={initialDir!.TrimEnd('/')}/");
+
+        var (zStarted, zExit, zOut) = await RunAsync("zenity", zenityArgs);
+        if (zStarted)
+            return zExit == 0 && !string.IsNullOrWhiteSpace(zOut)
+                ? new FolderPickResult(PickerOutcome.Chosen, zOut)
+                : new FolderPickResult(PickerOutcome.Cancelled, null);
+
+        var (kStarted, kExit, kOut) = await RunAsync("kdialog",
+            ["--getexistingdirectory", string.IsNullOrWhiteSpace(initialDir) ? "." : initialDir!]);
+        if (kStarted)
+            return kExit == 0 && !string.IsNullOrWhiteSpace(kOut)
+                ? new FolderPickResult(PickerOutcome.Chosen, kOut)
+                : new FolderPickResult(PickerOutcome.Cancelled, null);
+
+        return new FolderPickResult(PickerOutcome.Unavailable, null);
+    }
+
+    private static async Task<(bool Started, int ExitCode, string StdOut)> RunAsync(string fileName, IEnumerable<string> args)
+    {
+        var psi = new ProcessStartInfo(fileName)
+        {
+            RedirectStandardOutput = true,
+            RedirectStandardError = true,
+            UseShellExecute = false,
+            CreateNoWindow = true,
+        };
+        foreach (var arg in args)
+            psi.ArgumentList.Add(arg);
+
+        try
+        {
+            using var process = Process.Start(psi);
+            if (process is null)
+                return (false, -1, string.Empty);
+
+            var stdout = await process.StandardOutput.ReadToEndAsync();
+            await process.WaitForExitAsync();
+            return (true, process.ExitCode, stdout.Trim());
+        }
+        catch (Exception ex) when (ex is System.ComponentModel.Win32Exception or FileNotFoundException)
+        {
+            // Executable not found on PATH → treat as "no native picker".
+            return (false, -1, string.Empty);
+        }
+    }
+}

src/EchoHub.Client/Services/OutgoingAttachment.cs

@@ -0,0 +1,13 @@
+namespace EchoHub.Client.Services;
+
+/// <summary>
+/// One file to upload as part of a message. For end-to-end encrypted channels the stream
+/// is already ciphertext, <see cref="DeclaredKind"/> is set (image/audio/file), and
+/// <see cref="EncryptedPreview"/> holds the room-encrypted ASCII art for images.
+/// For normal channels only <see cref="Stream"/> and <see cref="FileName"/> are set.
+/// </summary>
+public sealed record OutgoingAttachment(
+    Stream Stream,
+    string FileName,
+    string? DeclaredKind = null,
+    string? EncryptedPreview = null);

src/EchoHub.Client/UI/Chat/ChatLine.cs

@@ -18,7 +18,7 @@ public partial class ChatLine
     public bool IsMention { get; set; }
     public string? AttachmentUrl { get; set; }
     public string? AttachmentFileName { get; set; }
-    public MessageType? Type { get; set; }
+    public AttachmentKind? AttachmentKind { get; set; }
     public string? SenderUsername { get; set; }
     /// <summary>Number of spaces to prepend on continuation lines when this line is word-wrapped.</summary>
     public int ContinuationIndent { get; set; }
@@ -124,7 +124,7 @@ public partial class ChatLine
         {
             wrapped.AttachmentUrl = AttachmentUrl;
             wrapped.AttachmentFileName = AttachmentFileName;
-            wrapped.Type = Type;
+            wrapped.AttachmentKind = AttachmentKind;
             wrapped.MessageId = MessageId;
             wrapped.SenderUsername = SenderUsername;
         }

src/EchoHub.Client/UI/Chat/ChatMessageManager.cs

@@ -238,86 +238,77 @@ public sealed class ChatMessageManager
         var senderName = message.SenderUsername + ":";
         var senderColor = HexColorHelper.ParseHexColor(message.SenderNicknameColor);
 
+        var indent = new string(' ', $"[{time}] {senderName} ".Length);
+        var pad = new string(' ', 7);
+
         var lines = new List<ChatLine>();
+        var hasContent = !string.IsNullOrWhiteSpace(message.Content);
+        var attachments = message.Attachments ?? [];
 
-        switch (message.Type)
+        // Header line: caption text, or a summary when the message is attachments-only
+        if (hasContent)
         {
-            case MessageType.Image:
-                lines.Add(BuildChatLine(time, senderName, senderColor, " [Image]"));
-                if (!string.IsNullOrWhiteSpace(message.Content))
-                {
-                    foreach (var artLine in message.Content.Split('\n'))
+            var displayContent = EmojiHelper.ReplaceEmoji(message.Content);
+            var contentLines = displayContent.Split('\n');
+            lines.Add(BuildChatLineWithMentions(time, senderName, senderColor, $" {contentLines[0].TrimEnd('\r')}"));
+            for (int i = 1; i < contentLines.Length; i++)
+                lines.Add(new ChatLine(ChatColors.SplitMentions($"{indent}{contentLines[i].TrimEnd('\r')}")));
+        }
+        else
+        {
+            var summary = attachments.Count switch
+            {
+                0 => " ",
+                1 => $" [{attachments[0].Kind.ToString().ToLowerInvariant()}]",
+                _ => $" [{attachments.Count} attachments]",
+            };
+            lines.Add(BuildChatLine(time, senderName, senderColor, summary));
+        }
+
+        foreach (var l in lines)
+            l.ContinuationIndent = indent.Length;
+
+        // One block per attachment
+        foreach (var attachment in attachments)
+        {
+            switch (attachment.Kind)
+            {
+                case Core.Models.AttachmentKind.Image:
+                    if (!string.IsNullOrWhiteSpace(attachment.AsciiPreview))
                     {
-                        var trimmed = artLine.TrimEnd('\r');
-                        if (ChatLine.HasColorTags(trimmed))
-                            lines.Add(ChatLine.FromColoredText("       " + trimmed));
-                        else
-                            lines.Add(new ChatLine($"       {trimmed}"));
+                        foreach (var artLine in attachment.AsciiPreview.Split('\n'))
+                        {
+                            var trimmed = artLine.TrimEnd('\r');
+                            lines.Add(ChatLine.HasColorTags(trimmed)
+                                ? ChatLine.FromColoredText(pad + trimmed)
+                                : new ChatLine($"{pad}{trimmed}"));
+                        }
                     }
-                }
+                    lines.Add(AttachmentActionLine(pad,
+                        $"[↓ save original] {attachment.FileName} [{FormatFileSize(attachment.FileSize)}]",
+                        ChatColors.FileAttr, attachment));
+                    break;
 
-                // Clickable action to download the original image below the ASCII art
-                if (message.AttachmentUrl is not null)
-                {
-                    var imageName = message.AttachmentFileName ?? "image";
-                    var imageSize = FormatFileSize(message.AttachmentFileSize);
-                    var saveLine = new ChatLine(new List<ChatSegment>
-                    {
-                        new("       ", null),
-                        new($"[↓ save original] {imageName} [{imageSize}]", ChatColors.FileAttr),
-                    });
-                    saveLine.AttachmentUrl = message.AttachmentUrl;
-                    saveLine.AttachmentFileName = imageName;
-                    saveLine.Type = MessageType.Image;
-                    lines.Add(saveLine);
-                }
-                break;
+                case Core.Models.AttachmentKind.Audio:
+                    lines.Add(AttachmentActionLine(pad,
+                        $"♪ [Audio: {attachment.FileName}] [{FormatFileSize(attachment.FileSize)}]",
+                        ChatColors.AudioAttr, attachment));
+                    break;
 
-            case MessageType.Audio:
-                var audioName = message.AttachmentFileName ?? "unknown";
-                var audioSize = FormatFileSize(message.AttachmentFileSize);
-                var audioLine = BuildChatLineColored(time, senderName, senderColor,
-                    $" \u266a [Audio: {audioName}] [{audioSize}]", ChatColors.AudioAttr);
-                audioLine.AttachmentUrl = message.AttachmentUrl;
-                audioLine.AttachmentFileName = audioName;
-                audioLine.Type = MessageType.Audio;
-                lines.Add(audioLine);
-                break;
+                default:
+                    lines.Add(AttachmentActionLine(pad,
+                        $"[File: {attachment.FileName}] [{FormatFileSize(attachment.FileSize)}]",
+                        ChatColors.FileAttr, attachment));
+                    break;
+            }
+        }
 
-            case MessageType.File:
-                var fileName = message.AttachmentFileName ?? "unknown";
-                var fileSize = FormatFileSize(message.AttachmentFileSize);
-                var fileLine = BuildChatLineColored(time, senderName, senderColor,
-                    $" [File: {fileName}] [{fileSize}]", ChatColors.FileAttr);
-                fileLine.AttachmentUrl = message.AttachmentUrl;
-                fileLine.AttachmentFileName = fileName;
-                fileLine.Type = MessageType.File;
-                lines.Add(fileLine);
-                break;
-
-            case MessageType.Text:
-            default:
-                var displayContent = EmojiHelper.ReplaceEmoji(message.Content);
-                var contentLines = displayContent.Split('\n');
-                var firstLine = contentLines[0].TrimEnd('\r');
-                lines.Add(BuildChatLineWithMentions(time, senderName, senderColor, $" {firstLine}"));
-                var indent = new string(' ', $"[{time}] {senderName} ".Length);
-                for (int i = 1; i < contentLines.Length; i++)
-                {
-                    var contText = $"{indent}{contentLines[i].TrimEnd('\r')}";
-                    lines.Add(new ChatLine(ChatColors.SplitMentions(contText)));
-                }
-
-                foreach (var l in lines)
-                    l.ContinuationIndent = indent.Length;
-
-                if (message.Embeds is { Count: > 0 })
-                {
-                    var chatWidth = _chatWidth > 0 ? _chatWidth : 80;
-                    foreach (var embed in message.Embeds)
-                        lines.AddRange(FormatEmbed(embed, indent, chatWidth));
-                }
-                break;
+        // Link embeds (from caption URLs)
+        if (message.Embeds is { Count: > 0 })
+        {
+            var chatWidth = _chatWidth > 0 ? _chatWidth : 80;
+            foreach (var embed in message.Embeds)
+                lines.AddRange(FormatEmbed(embed, indent, chatWidth));
         }
 
         foreach (var line in lines)
@@ -326,7 +317,7 @@ public sealed class ChatMessageManager
             line.SenderUsername = message.SenderUsername;
         }
 
-        if (!string.IsNullOrEmpty(_currentUser) && message.Type == MessageType.Text)
+        if (hasContent && !string.IsNullOrEmpty(_currentUser))
         {
             var pattern = $@"@{Regex.Escape(_currentUser)}\b";
             if (Regex.IsMatch(message.Content, pattern, RegexOptions.IgnoreCase))
@@ -339,6 +330,23 @@ public sealed class ChatMessageManager
         return lines;
     }
 
+    /// <summary>
+    /// Builds a clickable attachment line carrying the metadata the message list uses to
+    /// route activation (play audio, download file, save original image).
+    /// </summary>
+    private static ChatLine AttachmentActionLine(string pad, string text, Attribute color, AttachmentDto attachment)
+    {
+        var line = new ChatLine(new List<ChatSegment>
+        {
+            new(pad, null),
+            new(text, color),
+        });
+        line.AttachmentUrl = attachment.Url;
+        line.AttachmentFileName = attachment.FileName;
+        line.AttachmentKind = attachment.Kind;
+        return line;
+    }
+
     private static ChatLine BuildChatLine(string time, string senderName, Attribute? senderColor, string suffix)
     {
         var segments = new List<ChatSegment>

src/EchoHub.Client/UI/Helpers/DroppedFileParser.cs

@@ -0,0 +1,104 @@
+using System.Text;
+
+namespace EchoHub.Client.UI.Helpers;
+
+/// <summary>
+/// Recognizes a dragged-and-dropped file (or files) that a terminal delivers into the input as an
+/// absolute path. Terminals differ: some paste the whole path at once, others send it character by
+/// character; either way this checks whether the current input text resolves to existing file(s).
+/// </summary>
+public static class DroppedFileParser
+{
+    /// <summary>
+    /// Cheap pre-check so callers only stat the filesystem when the input plausibly holds a path:
+    /// a quoted path, a Windows drive path (<c>X:\</c>/<c>X:/</c>), a UNC path (<c>\\</c>), or a
+    /// POSIX absolute path (<c>/</c>). Normal chat text never starts this way.
+    /// </summary>
+    public static bool LooksLikePath(string text)
+    {
+        var t = text.TrimStart();
+        if (t.Length < 3)
+            return false;
+        if (t[0] is '"' or '/')
+            return true;
+        if (t.StartsWith(@"\\", StringComparison.Ordinal))
+            return true;
+        return char.IsLetter(t[0]) && t[1] == ':' && (t[2] == '\\' || t[2] == '/');
+    }
+
+    /// <summary>
+    /// Returns true when <paramref name="text"/> resolves to one or more existing files.
+    /// Handles a single path (quoted or not, possibly containing spaces) and multiple
+    /// space-separated (optionally quoted) paths. <paramref name="fileExists"/> is injectable
+    /// for testing; production passes <see cref="File.Exists"/>.
+    /// </summary>
+    public static bool TryGetFiles(string text, out List<string> files, Func<string, bool>? fileExists = null)
+    {
+        fileExists ??= File.Exists;
+        files = [];
+
+        var trimmed = text.Trim();
+        if (trimmed.Length < 3 || trimmed.Length > 4096 || trimmed.Contains('\n'))
+            return false;
+
+        // Single path, possibly quoted and/or containing spaces.
+        var unquoted = StripQuotes(trimmed);
+        if (Path.IsPathFullyQualified(unquoted) && fileExists(unquoted))
+        {
+            files.Add(unquoted);
+            return true;
+        }
+
+        // Multiple files: space-separated tokens, each optionally quoted.
+        foreach (var token in TokenizeQuoted(trimmed))
+        {
+            if (!Path.IsPathFullyQualified(token) || !fileExists(token))
+            {
+                files.Clear();
+                return false;
+            }
+            files.Add(token);
+        }
+
+        return files.Count > 0;
+    }
+
+    private static string StripQuotes(string s) =>
+        s.Length >= 2 && ((s[0] == '"' && s[^1] == '"') || (s[0] == '\'' && s[^1] == '\''))
+            ? s[1..^1]
+            : s;
+
+    private static IEnumerable<string> TokenizeQuoted(string input)
+    {
+        var current = new StringBuilder();
+        var quote = '\0';
+
+        foreach (var c in input)
+        {
+            if (quote != '\0')
+            {
+                if (c == quote) quote = '\0';
+                else current.Append(c);
+            }
+            else if (c is '"' or '\'')
+            {
+                quote = c;
+            }
+            else if (c == ' ')
+            {
+                if (current.Length > 0)
+                {
+                    yield return current.ToString();
+                    current.Clear();
+                }
+            }
+            else
+            {
+                current.Append(c);
+            }
+        }
+
+        if (current.Length > 0)
+            yield return current.ToString();
+    }
+}

src/EchoHub.Client/UI/MainWindow.cs

@@ -40,7 +40,9 @@ public sealed partial class MainWindow : Runnable
     private readonly UserListSource _usersListSource;
     private bool _usersPanelVisible = true;
     private const int UsersPanelWidth = 22;
+    private const string DefaultInputTitle = "Message │ Enter=send │ Ctrl+N=newline │ Tab=complete │ Ctrl+K=search";
     private static readonly Key F2Key = Key.F2;
+    private bool _hasStagedAttachments;
 
     internal static readonly string AppVersion =
         typeof(MainWindow).Assembly.GetName().Version?.ToString(3) ?? "?";
@@ -60,7 +62,7 @@ public sealed partial class MainWindow : Runnable
     private static readonly string[] SlashCommands =
     [
         "/status", "/nick", "/color", "/theme", "/send",
-        "/avatar", "/profile", "/servers", "/join", "/passwd", "/leave",
+        "/avatar", "/profile", "/servers", "/join", "/passwd", "/leave", "/clear", "/downloadpath",
         "/topic", "/users", "/kick", "/ban", "/unban",
         "/mute", "/unmute", "/role", "/nuke", "/test-sound", "/quit", "/help"
     ];
@@ -159,6 +161,11 @@ public sealed partial class MainWindow : Runnable
     /// </summary>
     public event Action<string, string>? OnImageSaveRequested;
 
+    /// <summary>
+    /// Fired when the user presses Delete on the selected message. Parameter is the message id.
+    /// </summary>
+    public event Action<Guid>? OnDeleteMessageRequested;
+
     /// <summary>
     /// Fired when the user activates a username (in userlist or message). Parameter is the username.
     /// </summary>
@@ -240,6 +247,7 @@ public sealed partial class MainWindow : Runnable
         };
         _messageList.Source = new ChatListSource();
         _messageList.Accepting += OnMessageListAccepting;
+        _messageList.KeyDown += OnMessageListKeyDown;
         _messageList.VerticalScrollBar.Scrolled += OnMessageListVerticalScrollBarScrolled;
         _messageList.VerticalScrollBar.Visible = true;
 
@@ -249,7 +257,7 @@ public sealed partial class MainWindow : Runnable
         // Bottom input area
         _inputFrame = new FrameView
         {
-            Title = "Message \u2502 Enter=send \u2502 Ctrl+N=newline \u2502 Tab=complete \u2502 Ctrl+K=search",
+            Title = DefaultInputTitle,
             X = 22,
             Y = Pos.Bottom(_chatFrame),
             Width = Dim.Fill(UsersPanelWidth),
@@ -321,6 +329,27 @@ public sealed partial class MainWindow : Runnable
         KeyDown += OnWindowKeyDown;
     }
 
+    /// <summary>
+    /// Updates the attachment staging indicator shown on the input frame's title.
+    /// Passing an empty list restores the default hint.
+    /// </summary>
+    public void SetStagedAttachments(IReadOnlyList<string> fileNames)
+    {
+        _hasStagedAttachments = fileNames.Count > 0;
+        if (fileNames.Count == 0)
+        {
+            _inputFrame.Title = DefaultInputTitle;
+        }
+        else
+        {
+            var names = string.Join(", ", fileNames);
+            if (names.Length > 60)
+                names = names[..57] + "...";
+            _inputFrame.Title = $"📎 {fileNames.Count} staged: {names} │ Enter=send │ /clear to drop";
+        }
+        _inputFrame.SetNeedsDraw();
+    }
+
     /// <summary>
     /// Applies the currently registered color schemes to all views.
     /// Call after theme changes to refresh colors.
@@ -458,21 +487,21 @@ public sealed partial class MainWindow : Runnable
         // Audio/file attachments take priority
         if (line.AttachmentUrl is not null && line.AttachmentFileName is not null)
         {
-            if (line.Type == MessageType.Audio)
+            if (line.AttachmentKind == AttachmentKind.Audio)
             {
                 OnAudioPlayRequested?.Invoke(line.AttachmentUrl, line.AttachmentFileName);
                 e.Handled = true;
                 return;
             }
 
-            if (line.Type == MessageType.File)
+            if (line.AttachmentKind == AttachmentKind.File)
             {
                 OnFileDownloadRequested?.Invoke(line.AttachmentUrl, line.AttachmentFileName);
                 e.Handled = true;
                 return;
             }
 
-            if (line.Type == MessageType.Image)
+            if (line.AttachmentKind == AttachmentKind.Image)
             {
                 OnImageSaveRequested?.Invoke(line.AttachmentUrl, line.AttachmentFileName);
                 e.Handled = true;
@@ -510,6 +539,32 @@ public sealed partial class MainWindow : Runnable
         }
     }
 
+    private void OnMessageListKeyDown(object? sender, Key e)
+    {
+        if (e.KeyCode != Key.Delete.KeyCode && e.KeyCode != Key.Backspace.KeyCode)
+            return;
+
+        if (_messageList.Source is not ChatListSource source)
+            return;
+
+        var index = _messageList.SelectedItem;
+        if (!index.HasValue || index.Value < 0 || index.Value >= source.Count)
+            return;
+
+        var line = source.GetLine(index.Value);
+        if (line?.MessageId is not { } messageId)
+            return;
+
+        // Server enforces the real permission (own message, or Mod+ over a lower role);
+        // the client just confirms intent and lets the server reject if disallowed.
+        var confirm = MessageBox.Query(_app, "Delete Message",
+            "Delete this message?", "Delete", "Cancel");
+        if (confirm == 0)
+            OnDeleteMessageRequested?.Invoke(messageId);
+
+        e.Handled = true;
+    }
+
     private void OnMessageListVerticalScrollBarScrolled(object? sender, EventArgs<int> e)
     {
         if (_messageList.VerticalScrollBar.Value == 0)
@@ -545,7 +600,9 @@ public sealed partial class MainWindow : Runnable
         else if (e.KeyCode == EnterKey.KeyCode)
         {
             var text = _inputField.Text?.Trim() ?? string.Empty;
-            if (!string.IsNullOrEmpty(text) && !string.IsNullOrEmpty(_messageManager.CurrentChannel))
+            // Send when there's text, or when only attachments are staged (empty caption).
+            if ((!string.IsNullOrEmpty(text) || _hasStagedAttachments)
+                && !string.IsNullOrEmpty(_messageManager.CurrentChannel))
             {
                 OnMessageSubmitted?.Invoke(_messageManager.CurrentChannel, text);
                 _inputField.Text = string.Empty;
@@ -564,9 +621,13 @@ public sealed partial class MainWindow : Runnable
         }
         else if (e.KeyCode == CtrlVKey.KeyCode || e.KeyCode == CtrlYKey.KeyCode)
         {
-            // Explicit paste support: terminals that don't intercept Ctrl+V themselves
-            // otherwise leave users with only the right-click context menu.
-            GuardedClipboardAction(() => _inputField.Paste(), "paste");
+            // If a file was copied in the OS file manager, the clipboard holds a file list
+            // (not text) — attach it. Otherwise paste text. This is the reliable path on
+            // Windows Terminal, which never pastes copied files as text.
+            if (ClipboardFiles.TryGetFiles(out var pastedFiles))
+                StageFiles(pastedFiles);
+            else
+                GuardedClipboardAction(() => _inputField.Paste(), "paste");
             e.Handled = true;
         }
         else if (e.KeyCode == CtrlXKey.KeyCode)
@@ -599,42 +660,35 @@ public sealed partial class MainWindow : Runnable
     }
 
     private bool _suppressEmojiReplace;
-    private int _lastInputLength;
 
     private void OnInputContentsChanged(object? sender, ContentsChangedEventArgs e)
     {
-        var text = _inputField.Text;
-        var previousLength = _lastInputLength;
-        _lastInputLength = text?.Length ?? 0;
-
         if (_suppressEmojiReplace)
             return;
 
+        var text = _inputField.Text;
         if (string.IsNullOrEmpty(text))
             return;
 
-        // A file dropped onto the terminal arrives as a pasted absolute path.
-        // Detect multi-char bursts that resolve to existing files and route them
-        // through /send instead of leaving a raw path in the input.
-        if (text.Length - previousLength > 3 && TryGetDroppedFiles(text, out var droppedFiles))
+        // A file dropped onto the terminal is delivered as its absolute path inserted into the
+        // input — often character by character (this Terminal.Gui build has no bracketed-paste
+        // coalescing). As soon as the input resolves to existing file path(s), route them
+        // through /send (which stages them) instead of leaving a raw path to be sent as a message.
+        if (DroppedFileParser.LooksLikePath(text) && DroppedFileParser.TryGetFiles(text, out var droppedFiles)
+            && !string.IsNullOrEmpty(_messageManager.CurrentChannel))
         {
-            var channel = _messageManager.CurrentChannel;
-            if (!string.IsNullOrEmpty(channel))
+            _suppressEmojiReplace = true;
+            try
             {
-                _suppressEmojiReplace = true;
-                try
-                {
-                    _inputField.Text = string.Empty;
-                }
-                finally
-                {
-                    _suppressEmojiReplace = false;
-                }
-
-                foreach (var file in droppedFiles)
-                    OnMessageSubmitted?.Invoke(channel, $"/send \"{file}\"");
-                return;
+                _inputField.Text = string.Empty;
             }
+            finally
+            {
+                _suppressEmojiReplace = false;
+            }
+
+            StageFiles(droppedFiles);
+            return;
         }
 
         var replaced = EmojiHelper.ReplaceEmoji(text);
@@ -695,77 +749,17 @@ public sealed partial class MainWindow : Runnable
     }
 
     /// <summary>
-    /// Interprets pasted text as one or more dropped files. Terminals deliver a file drop
-    /// as the absolute path (quoted when it contains spaces; multiple files space-separated).
-    /// Returns true only when the entire input resolves to existing files.
+    /// Routes files (from a drop or a file-clipboard paste) through the /send pipeline, which
+    /// stages them; the next Enter sends them with any typed caption.
     /// </summary>
-    private static bool TryGetDroppedFiles(string text, out List<string> files)
+    private void StageFiles(IEnumerable<string> files)
     {
-        files = [];
+        var channel = _messageManager.CurrentChannel;
+        if (string.IsNullOrEmpty(channel))
+            return;
 
-        var trimmed = text.Trim();
-        if (trimmed.Length < 3 || trimmed.Length > 4096 || trimmed.Contains('\n'))
-            return false;
-
-        // Single unquoted path, possibly with spaces (e.g. WSL or plain conhost drops)
-        var unquoted = StripQuotes(trimmed);
-        if (Path.IsPathFullyQualified(unquoted) && File.Exists(unquoted))
-        {
-            files.Add(unquoted);
-            return true;
-        }
-
-        // Multiple files: space-separated tokens, each optionally quoted
-        foreach (var token in TokenizeQuoted(trimmed))
-        {
-            if (!Path.IsPathFullyQualified(token) || !File.Exists(token))
-            {
-                files.Clear();
-                return false;
-            }
-            files.Add(token);
-        }
-
-        return files.Count > 0;
-    }
-
-    private static string StripQuotes(string s) =>
-        s.Length >= 2 && ((s[0] == '"' && s[^1] == '"') || (s[0] == '\'' && s[^1] == '\''))
-            ? s[1..^1]
-            : s;
-
-    private static IEnumerable<string> TokenizeQuoted(string input)
-    {
-        var current = new System.Text.StringBuilder();
-        var quote = '\0';
-
-        foreach (var c in input)
-        {
-            if (quote != '\0')
-            {
-                if (c == quote) quote = '\0';
-                else current.Append(c);
-            }
-            else if (c is '"' or '\'')
-            {
-                quote = c;
-            }
-            else if (c == ' ')
-            {
-                if (current.Length > 0)
-                {
-                    yield return current.ToString();
-                    current.Clear();
-                }
-            }
-            else
-            {
-                current.Append(c);
-            }
-        }
-
-        if (current.Length > 0)
-            yield return current.ToString();
+        foreach (var file in files)
+            OnMessageSubmitted?.Invoke(channel, $"/send \"{file}\"");
     }
 
     private void OnChatViewportChanged()