feat(ui): enable drag-and-drop attachments and image previews in chat (#390)

* feat(BottomTerminalDock): add close button next to the fullscreen toggle in the dock

* style: replace hardcoded gradient with theme value in shine text variant

* fix(header): adapt instance button for desktop only

* refactor(chat): polish sticky turn UX and message action rows for better readability

Switch to stable sticky-only turn behavior and redesign user/assistant action controls (placement, hover rules, ordering, spacing, selection-safe clamp) to reduce visual noise and improve interaction flow.

* feat(chat/message): refactor buttons in messages footer

* feat: enhance image preview functionality in chat messages

- Added a new ImagePreviewDialog component to handle image previews with navigation support.
- Updated ToolOutputDialog to utilize the new ImagePreviewDialog for displaying images.
- Modified the ToolPopupContent type to include a gallery of images and an index for the current image.
- Removed the old inline image display logic from ToolOutputDialog.
- Improved file handling in the file store, including better MIME type guessing and handling of server paths.
- Introduced a new API endpoint for handling large session message payloads, allowing for better management of multi-file attachments.
- Updated the VSCode bridge to support session message requests with appropriate headers and body handling.

* feat(proxy): implement SSE forwarding and enhance generic API request handling

* feat(chat): support submitting only queued messages

* feat: add image preview transition state

* fix: default VSCode view to draft and fixed sessions list regression

packages/desktop/src-tauri/src/main.rs

@@ -1843,6 +1843,65 @@ fn desktop_new_window_at_url(app: tauri::AppHandle, url: String) -> Result<(), S
     create_window(&app, &url, &local_origin).map_err(|e| e.to_string())
 }
 
+/// Read a file and return its content as base64 with mime type detection.
+/// Used for drag-drop file attachments in desktop app.
+#[tauri::command]
+fn desktop_read_file(path: String) -> Result<FileContent, String> {
+    use std::path::Path;
+
+    let path = Path::new(&path);
+
+    // Check file size (max 50MB)
+    let metadata = std::fs::metadata(path).map_err(|e| format!("Failed to read file metadata: {e}"))?;
+    let size = metadata.len();
+    if size > 50 * 1024 * 1024 {
+        return Err("File is too large. Maximum size is 50MB.".to_string());
+    }
+
+    // Read file bytes
+    let bytes = std::fs::read(path).map_err(|e| format!("Failed to read file: {e}"))?;
+
+    // Detect mime type from extension
+    let ext = path.extension().and_then(|e| e.to_str()).unwrap_or("").to_lowercase();
+    let mime = match ext.as_str() {
+        "png" => "image/png",
+        "jpg" | "jpeg" => "image/jpeg",
+        "gif" => "image/gif",
+        "webp" => "image/webp",
+        "svg" => "image/svg+xml",
+        "bmp" => "image/bmp",
+        "ico" => "image/x-icon",
+        "pdf" => "application/pdf",
+        "txt" => "text/plain",
+        "md" => "text/markdown",
+        "json" => "application/json",
+        "js" => "text/javascript",
+        "ts" => "text/typescript",
+        "tsx" => "text/typescript-jsx",
+        "jsx" => "text/javascript-jsx",
+        "html" => "text/html",
+        "css" => "text/css",
+        "py" => "text/x-python",
+        _ => "application/octet-stream",
+    };
+
+    // Encode as base64
+    let base64 = general_purpose::STANDARD.encode(&bytes);
+
+    Ok(FileContent {
+        mime: mime.to_string(),
+        base64,
+        size: bytes.len(),
+    })
+}
+
+#[derive(Serialize)]
+struct FileContent {
+    mime: String,
+    base64: String,
+    size: usize,
+}
+
 #[cfg(target_os = "macos")]
 fn macos_major_version() -> Option<u32> {
     fn cmd_stdout(cmd: &str, args: &[&str]) -> Option<String> {
@@ -2222,6 +2281,7 @@ fn main() {
             desktop_hosts_get,
             desktop_hosts_set,
             desktop_host_probe,
+            desktop_read_file,
         ])
         .setup(|app| {
             let handle = app.handle().clone();

packages/desktop/src-tauri/tauri.conf.json

@@ -27,6 +27,7 @@
           "x": 17,
           "y": 26
         },
+        "dragDropEnabled": false,
         "visible": false,
         "backgroundThrottling": "disabled"
       }

packages/ui/src/components/chat/ChatInput.tsx

@@ -36,7 +36,7 @@ import { useCurrentSessionActivity } from '@/hooks/useSessionActivity';
 import { toast } from '@/components/ui';
 import { useFileStore } from '@/stores/fileStore';
 import { useMessageStore } from '@/stores/messageStore';
-import { isVSCodeRuntime } from '@/lib/desktop';
+import { isDesktopLocalOriginActive, isTauriShell, isVSCodeRuntime } from '@/lib/desktop';
 import { isIMECompositionEvent } from '@/lib/ime';
 import { StopIcon } from '@/components/icons/StopIcon';
 import type { MobileControlsPanel } from './mobileControlsUtils';
@@ -53,7 +53,7 @@ const EMPTY_QUEUE: QueuedMessage[] = [];
 
 interface ChatInputProps {
     onOpenSettings?: () => void;
-    scrollToBottom?: (options?: { instant?: boolean; force?: boolean; clearAnchor?: boolean }) => void;
+    scrollToBottom?: (options?: { instant?: boolean; force?: boolean }) => void;
 }
 
 const CHAT_INPUT_DRAFT_KEY = 'openchamber_chat_input_draft';
@@ -95,6 +95,7 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
     const [draftMessage, setDraftMessage] = React.useState(''); // Preserves input when entering history mode
     const textareaRef = React.useRef<HTMLTextAreaElement>(null);
     const dropZoneRef = React.useRef<HTMLDivElement>(null);
+    const canAcceptDropRef = React.useRef(false);
     const mentionRef = React.useRef<FileMentionHandle>(null);
     const commandRef = React.useRef<CommandAutocompleteHandle>(null);
     const agentRef = React.useRef<AgentMentionAutocompleteHandle>(null);
@@ -373,7 +374,10 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
     const canAbort = working.isWorking;
 
     // Keep a ref to handleSubmit so callbacks don't depend on it.
-    const handleSubmitRef = React.useRef<(e?: React.FormEvent) => Promise<void>>(async () => {});
+    type SubmitOptions = {
+        queuedOnly?: boolean;
+    };
+    const handleSubmitRef = React.useRef<(options?: SubmitOptions) => Promise<void>>(async () => {});
 
     // Add message to queue instead of sending
     const handleQueueMessage = React.useCallback(() => {
@@ -403,10 +407,14 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
         }
     }, [hasContent, currentSessionId, message, attachedFiles, addToQueue, clearAttachedFiles, isMobile, consumeDrafts]);
 
-    const handleSubmit = async (e?: React.FormEvent) => {
-        e?.preventDefault();
+    const handleSubmit = async (options?: SubmitOptions) => {
+        const queuedOnly = options?.queuedOnly ?? false;
 
-        if (!canSend || (!currentSessionId && !newSessionDraftOpen)) return;
+        if (queuedOnly) {
+            if (!hasQueuedMessages || !currentSessionId) return;
+        } else if (!canSend || (!currentSessionId && !newSessionDraftOpen)) {
+            return;
+        }
 
         // Re-pin and scroll to bottom when sending
         scrollToBottom?.({ instant: true, force: true });
@@ -448,8 +456,8 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
             }
         }
 
-        // Add current input
-        if (hasContent) {
+        // Add current input (skip for queued-only auto-send)
+        if (!queuedOnly && hasContent) {
             const messageToSend = message.replace(/^\n+|\n+$/g, '');
             const { sanitizedText, mention } = parseAgentMentions(messageToSend, agents);
             const attachmentsToSend = attachedFiles.map((file) => ({ ...file }));
@@ -473,7 +481,7 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
 
         const sessionKey = currentSessionId ?? (newSessionDraftOpen ? 'draft' : null);
         let drafts: InlineCommentDraft[] = [];
-        if (sessionKey) {
+        if (!queuedOnly && sessionKey) {
             drafts = consumeDrafts(sessionKey);
         }
 
@@ -504,12 +512,14 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
         if (currentSessionId && hasQueuedMessages) {
             clearQueue(currentSessionId);
         }
-        setMessage('');
-        // Reset message history navigation state
-        setHistoryIndex(-1);
-        setDraftMessage('');
-        if (attachedFiles.length > 0) {
-            clearAttachedFiles();
+        if (!queuedOnly) {
+            setMessage('');
+            // Reset message history navigation state
+            setHistoryIndex(-1);
+            setDraftMessage('');
+            if (attachedFiles.length > 0) {
+                clearAttachedFiles();
+            }
         }
 
         if (isMobile) {
@@ -615,6 +625,10 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
             }
 
             if (isSoftNetworkError) {
+                if (allAttachments.length > 0) {
+                    useFileStore.setState({ attachedFiles: allAttachments });
+                    toast.error('Failed to send attachments. Try fewer files or smaller images.');
+                }
                 return;
             }
 
@@ -662,7 +676,7 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
             // Use setTimeout to avoid calling during render
             setTimeout(() => {
                 if (currentSessionId && currentProviderId && currentModelId) {
-                    void handleSubmitRef.current();
+                    void handleSubmitRef.current({ queuedOnly: true });
                 }
                 autoSendTriggeredRef.current = false;
             }, 100);
@@ -1278,7 +1292,59 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
         }
     }, [abortPromptSessionId, currentSessionId, clearAbortPrompt]);
 
-    const handleDragOver = (e: React.DragEvent) => {
+    React.useEffect(() => {
+        canAcceptDropRef.current = Boolean(currentSessionId || newSessionDraftOpen);
+    }, [currentSessionId, newSessionDraftOpen]);
+
+    const hasDraggedFiles = React.useCallback((dataTransfer: DataTransfer | null | undefined): boolean => {
+        if (!dataTransfer) return false;
+        if (dataTransfer.files && dataTransfer.files.length > 0) return true;
+        if (!dataTransfer.types) return false;
+        return Array.from(dataTransfer.types).includes('Files');
+    }, []);
+
+    const collectDroppedFiles = React.useCallback((dataTransfer: DataTransfer | null | undefined): File[] => {
+        if (!dataTransfer) return [];
+
+        const directFiles = Array.from(dataTransfer.files || []);
+        if (directFiles.length > 0) {
+            return directFiles;
+        }
+
+        const fromItems = Array.from(dataTransfer.items || [])
+            .filter((item) => item.kind === 'file')
+            .map((item) => item.getAsFile())
+            .filter((file): file is File => Boolean(file));
+
+        return fromItems;
+    }, []);
+
+    const normalizeDroppedPath = React.useCallback((rawPath: string): string => {
+        const input = rawPath.trim();
+        if (!input.toLowerCase().startsWith('file://')) {
+            return input;
+        }
+
+        try {
+            let pathname = decodeURIComponent(new URL(input).pathname || '');
+            if (/^\/[A-Za-z]:\//.test(pathname)) {
+                pathname = pathname.slice(1);
+            }
+            return pathname || input;
+        } catch {
+            const stripped = input.replace(/^file:\/\//i, '');
+            try {
+                return decodeURIComponent(stripped);
+            } catch {
+                return stripped;
+            }
+        }
+    }, []);
+
+    const handleDragEnter = (e: React.DragEvent) => {
+        if (!hasDraggedFiles(e.dataTransfer)) {
+            return;
+        }
         e.preventDefault();
         e.stopPropagation();
         if ((currentSessionId || newSessionDraftOpen) && !isDragging) {
@@ -1286,6 +1352,18 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
         }
     };
 
+    const handleDragOver = (e: React.DragEvent) => {
+        if (!hasDraggedFiles(e.dataTransfer)) {
+            return;
+        }
+        e.preventDefault();
+        e.stopPropagation();
+        e.dataTransfer.dropEffect = 'copy';
+        if ((currentSessionId || newSessionDraftOpen) && !isDragging) {
+            setIsDragging(true);
+        }
+    };
+
     const handleDragLeave = (e: React.DragEvent) => {
         e.preventDefault();
         e.stopPropagation();
@@ -1295,26 +1373,31 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
     };
 
     const handleDrop = async (e: React.DragEvent) => {
+        if (!hasDraggedFiles(e.dataTransfer)) {
+            return;
+        }
         e.preventDefault();
         e.stopPropagation();
         setIsDragging(false);
 
         if (!currentSessionId && !newSessionDraftOpen) return;
 
-        const files = Array.from(e.dataTransfer.files);
+        const files = collectDroppedFiles(e.dataTransfer);
         let attachedCount = 0;
 
-        for (const file of files) {
-            const sizeBefore = useSessionStore.getState().attachedFiles.length;
-            try {
-                await addAttachedFile(file);
-                const sizeAfter = useSessionStore.getState().attachedFiles.length;
-                if (sizeAfter > sizeBefore) {
-                    attachedCount += 1;
+        if (files.length > 0) {
+            for (const file of files) {
+                const sizeBefore = useSessionStore.getState().attachedFiles.length;
+                try {
+                    await addAttachedFile(file);
+                    const sizeAfter = useSessionStore.getState().attachedFiles.length;
+                    if (sizeAfter > sizeBefore) {
+                        attachedCount += 1;
+                    }
+                } catch (error) {
+                    console.error('File attach failed', error);
+                    toast.error(error instanceof Error ? error.message : 'Failed to attach file');
                 }
-            } catch (error) {
-                console.error('File attach failed', error);
-                toast.error(error instanceof Error ? error.message : 'Failed to attach file');
             }
         }
 
@@ -1323,6 +1406,120 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
         }
     };
 
+    // Tauri desktop: handle native file drops via onDragDropEvent
+    React.useEffect(() => {
+        if (!isTauriShell()) return;
+        let cancelled = false;
+        let unlisten: (() => void) | null = null;
+
+        void (async () => {
+            try {
+                const { getCurrentWebviewWindow } = await import('@tauri-apps/api/webviewWindow');
+                const webviewWindow = getCurrentWebviewWindow();
+                const removeListener = await webviewWindow.onDragDropEvent(async (event) => {
+                    if (!canAcceptDropRef.current) return;
+
+                    const payload = (event as { payload?: unknown }).payload;
+                    if (!payload || typeof payload !== 'object') return;
+
+                    const typed = payload as { type?: string; paths?: string[]; position?: { x?: number; y?: number } };
+                    const type = typed.type;
+                    const x = typed.position?.x;
+                    const y = typed.position?.y;
+
+                    // Check if drop is inside the chat input area
+                    const zone = dropZoneRef.current;
+                    let inZone = false;
+                    if (zone && typeof x === 'number' && typeof y === 'number') {
+                        const rect = zone.getBoundingClientRect();
+                        inZone = x >= rect.left && x <= rect.right && y >= rect.top && y <= rect.bottom;
+                        // Handle retina displays where Tauri might report physical pixels
+                        if (!inZone && window.devicePixelRatio > 1) {
+                            const sx = x / window.devicePixelRatio;
+                            const sy = y / window.devicePixelRatio;
+                            inZone = sx >= rect.left && sx <= rect.right && sy >= rect.top && sy <= rect.bottom;
+                        }
+                    }
+
+                    if (type === 'enter' || type === 'over') {
+                        setIsDragging(inZone);
+                        return;
+                    }
+                    if (type === 'leave') {
+                        setIsDragging(false);
+                        return;
+                    }
+                    if (type === 'drop') {
+                        setIsDragging(false);
+                        if (!inZone) return;
+
+                        const paths = Array.isArray(typed.paths)
+                            ? typed.paths.filter((p): p is string => typeof p === 'string')
+                            : [];
+                        if (paths.length === 0) return;
+
+                        let attachedCount = 0;
+                        for (const path of paths) {
+                            const sizeBefore = useSessionStore.getState().attachedFiles.length;
+                            try {
+                                const normalizedPath = normalizeDroppedPath(path);
+                                const fileName = normalizedPath.split(/[\\/]/).pop() || normalizedPath;
+                                let file: File;
+
+                                // In desktop shell on remote origin, local file paths are not readable via /api/fs/raw.
+                                // Read bytes from local machine via Tauri command.
+                                if (isTauriShell() && !isDesktopLocalOriginActive()) {
+                                    const { invoke } = await import('@tauri-apps/api/core');
+                                    const result = await invoke<{ mime: string; base64: string }>('desktop_read_file', { path: normalizedPath });
+                                    const byteCharacters = atob(result.base64);
+                                    const byteNumbers = new Array(byteCharacters.length);
+                                    for (let i = 0; i < byteCharacters.length; i++) {
+                                        byteNumbers[i] = byteCharacters.charCodeAt(i);
+                                    }
+                                    const byteArray = new Uint8Array(byteNumbers);
+                                    const blob = new Blob([byteArray], { type: result.mime || 'application/octet-stream' });
+                                    file = new File([blob], fileName, { type: result.mime || 'application/octet-stream' });
+                                } else {
+                                    const response = await fetch(`/api/fs/raw?path=${encodeURIComponent(normalizedPath)}`);
+                                    if (!response.ok) {
+                                        throw new Error(`Failed to read dropped file (${response.status})`);
+                                    }
+                                    const blob = await response.blob();
+                                    file = new File([blob], fileName, { type: blob.type || 'application/octet-stream' });
+                                }
+
+                                await addAttachedFile(file);
+                                const sizeAfter = useSessionStore.getState().attachedFiles.length;
+                                if (sizeAfter > sizeBefore) attachedCount++;
+                            } catch (error) {
+                                console.error('Failed to attach dropped file:', path, error);
+                                toast.error(`Failed to attach ${path.split(/[\\/]/).pop() || 'file'}`);
+                            }
+                        }
+                        if (attachedCount > 0) {
+                            toast.success(`Attached ${attachedCount} file${attachedCount > 1 ? 's' : ''}`);
+                        }
+                    }
+                });
+
+                if (cancelled) {
+                    removeListener();
+                    return;
+                }
+                unlisten = removeListener;
+            } catch (error) {
+                if (!cancelled) {
+                    console.warn('Failed to register Tauri drag-drop listener:', error);
+                }
+            }
+        })();
+
+        return () => {
+            cancelled = true;
+            if (unlisten) unlisten();
+        };
+    }, [addAttachedFile, normalizeDroppedPath]);
+
     const handleServerFilesSelected = React.useCallback(async (files: Array<{ path: string; name: string }>) => {
         let attachedCount = 0;
 
@@ -1708,35 +1905,7 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
                     showAbortStatus={showAbortStatus}
                 />
             </div>
-            <div
-                ref={dropZoneRef}
-                className={cn(
-                    "chat-column relative overflow-visible",
-                    isDragging && "ring-2 ring-primary ring-offset-2 rounded-xl"
-                )}
-
-                onDragOver={handleDragOver}
-                onDragLeave={handleDragLeave}
-                onDrop={handleDrop}
-            >
-                {isDragging && (
-                    <div className="absolute inset-0 z-50 flex items-center justify-center bg-background/80 backdrop-blur-sm rounded-xl">
-                        <div className="text-center">
-                            <div className="inline-flex justify-center">
-                                <button
-                                    type="button"
-                                    className={iconButtonBaseClass}
-                                    onClick={() => handlePickLocalFiles()}
-                                    title="Attach files"
-                                    aria-label="Attach files"
-                                >
-                                    <RiAttachment2 className={cn(iconSizeClass, 'text-current')} />
-                                </button>
-                            </div>
-                            <p className="mt-2 typography-ui-label text-muted-foreground">Drop files here to attach</p>
-                        </div>
-                    </div>
-                )}
+            <div className="chat-column relative overflow-visible">
                 <AttachedFilesList />
                 <QueuedMessageChips
                     onEditMessage={(content) => {
@@ -1766,13 +1935,37 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
                     className={cn(
                         "flex flex-col relative overflow-visible",
                         "border border-border/80",
-                        "focus-within:ring-1 focus-within:ring-primary/50"
+                        "focus-within:ring-1 focus-within:ring-primary/50",
+                        isDragging && "ring-2 ring-primary ring-offset-2"
                     )}
                     style={{
                         borderRadius: cornerRadius,
                         backgroundColor: currentTheme?.colors?.surface?.subtle,
                     }}
+                    ref={dropZoneRef}
+                    onDragEnter={handleDragEnter}
+                    onDragOver={handleDragOver}
+                    onDragLeave={handleDragLeave}
+                    onDrop={handleDrop}
                 >
+                    {isDragging && (
+                        <div className="absolute inset-0 z-50 flex items-center justify-center bg-background/80 backdrop-blur-sm rounded-xl">
+                            <div className="text-center">
+                                <div className="inline-flex justify-center">
+                                    <button
+                                        type="button"
+                                        className={iconButtonBaseClass}
+                                        onClick={() => handlePickLocalFiles()}
+                                        title="Attach files"
+                                        aria-label="Attach files"
+                                    >
+                                        <RiAttachment2 className={cn(iconSizeClass, 'text-current')} />
+                                    </button>
+                                </div>
+                                <p className="mt-2 typography-ui-label text-muted-foreground">Drop files here to attach</p>
+                            </div>
+                        </div>
+                    )}
 
                     {showCommandAutocomplete && (
                         <CommandAutocomplete
@@ -1826,6 +2019,9 @@ export const ChatInput: React.FC<ChatInputProps> = ({ onOpenSettings, scrollToBo
                         onChange={handleTextChange}
                         onKeyDown={handleKeyDown}
                         onPaste={handlePaste}
+                        onDragEnter={handleDragEnter}
+                        onDragOver={handleDragOver}
+                        onDrop={handleDrop}
                         onPointerDownCapture={handleTextareaPointerDownCapture}
                         placeholder={currentSessionId || newSessionDraftOpen
                             ? "# for agents; @ for files; / for commands"

packages/ui/src/components/chat/ChatMessage.tsx

@@ -888,7 +888,7 @@ const ChatMessage: React.FC<ChatMessageProps> = ({
                 className={cn(
                     'group w-full',
                     shouldShowHeader ? 'pt-6' : 'pt-0',
-                    isUser ? 'pb-4' : isFollowedByAssistant ? 'pb-0' : 'pb-8'
+                    isUser ? 'pb-0' : isFollowedByAssistant ? 'pb-0' : 'pb-8'
                 )}
                 data-message-id={message.info.id}
                 ref={messageContainerRef}

packages/ui/src/components/chat/FileAttachment.tsx

@@ -141,6 +141,7 @@ const FileChip = memo(({ file, onRemove }: FileChipProps) => {
   };
 
   const formatFileSize = (bytes: number) => {
+    if (!Number.isFinite(bytes) || bytes <= 0) return '...';
     if (bytes < 1024) return bytes + ' B';
     if (bytes < 1024 * 1024) return (bytes / 1024).toFixed(1) + ' KB';
     return (bytes / (1024 * 1024)).toFixed(1) + ' MB';
@@ -157,6 +158,32 @@ const FileChip = memo(({ file, onRemove }: FileChipProps) => {
   };
 
   const displayName = extractFilename(file.filename);
+  const isLocalImagePreview =
+    file.source !== 'server' &&
+    file.mimeType.startsWith('image/') &&
+    typeof file.dataUrl === 'string' &&
+    file.dataUrl.startsWith('data:image/');
+
+  if (isLocalImagePreview) {
+    return (
+      <div className="relative h-12 w-12 sm:h-14 sm:w-14 overflow-hidden rounded-lg border border-border/40 bg-muted/10 flex-shrink-0">
+        <img
+          src={file.dataUrl}
+          alt={displayName}
+          className="h-full w-full object-cover"
+          loading="lazy"
+        />
+        <button
+          onClick={onRemove}
+          className="absolute top-1 right-1 h-5 w-5 rounded-full bg-background/80 text-foreground hover:text-destructive flex items-center justify-center focus-visible:outline-none focus-visible:ring-1 focus-visible:ring-ring"
+          title="Remove image"
+          aria-label={`Remove ${displayName}`}
+        >
+          <RiCloseLine className="h-3 w-3" />
+        </button>
+      </div>
+    );
+  }
 
   return (
     <div className="flex w-full sm:inline-flex sm:w-auto items-center gap-1.5 px-3 sm:px-2.5 py-1 bg-muted/30 border border-border/30 rounded-xl typography-meta max-w-full min-w-0">
@@ -195,7 +222,6 @@ export const AttachedFilesList = memo(() => {
   return (
     <div className="pb-2 overflow-hidden">
       <div className="flex flex-col sm:flex-row sm:items-center sm:flex-wrap gap-2 px-3 py-2 bg-muted/30 rounded-xl border border-border/30">
-        <span className="typography-meta text-muted-foreground font-medium flex-shrink-0">Attached:</span>
         {attachedFiles.map((file) => (
           <FileChip
             key={file.id}
@@ -219,9 +245,10 @@ interface FilePart {
 interface MessageFilesDisplayProps {
   files: FilePart[];
   onShowPopup?: (content: ToolPopupContent) => void;
+  compact?: boolean;
 }
 
-export const MessageFilesDisplay = memo(({ files, onShowPopup }: MessageFilesDisplayProps) => {
+export const MessageFilesDisplay = memo(({ files, onShowPopup, compact = false }: MessageFilesDisplayProps) => {
 
   const fileItems = files.filter(f => f.type === 'file' && (f.mime || f.url));
 
@@ -251,12 +278,30 @@ export const MessageFilesDisplay = memo(({ files, onShowPopup }: MessageFilesDis
   const imageFiles = fileItems.filter(f => f.mime?.startsWith('image/') && f.url);
   const otherFiles = fileItems.filter(f => !f.mime?.startsWith('image/'));
 
-  const handleImageClick = React.useCallback((file: { filename?: string; mime?: string; size?: number; url?: string }) => {
-    if (!onShowPopup || !file?.url) {
+  const imageGallery = React.useMemo(
+    () =>
+      imageFiles.flatMap((file) => {
+          if (!file.url) return [];
+          const filename = extractFilename(file.filename) || 'Image';
+          return [{
+            url: file.url,
+            mimeType: file.mime,
+            filename,
+            size: file.size,
+          }];
+        }),
+    [imageFiles]
+  );
+
+  const handleImageClick = React.useCallback((index: number) => {
+    if (!onShowPopup) {
       return;
     }
 
-    const filename = extractFilename(file.filename) || 'Image';
+    const file = imageGallery[index];
+    if (!file?.url) return;
+
+    const filename = file.filename || 'Image';
 
     const popupPayload: ToolPopupContent = {
       open: true,
@@ -265,33 +310,39 @@ export const MessageFilesDisplay = memo(({ files, onShowPopup }: MessageFilesDis
       metadata: {
         tool: 'image-preview',
         filename,
-        mime: file.mime,
+        mime: file.mimeType,
         size: file.size,
       },
       image: {
         url: file.url,
-        mimeType: file.mime,
+        mimeType: file.mimeType,
         filename,
+        size: file.size,
+        gallery: imageGallery,
+        index,
       },
     };
 
     onShowPopup(popupPayload);
-  }, [onShowPopup]);
+  }, [imageGallery, onShowPopup]);
 
   if (fileItems.length === 0) return null;
 
   return (
-    <div className="space-y-2 mt-2">
+    <div className={cn(compact ? 'space-y-1.5 mt-1.5' : 'space-y-2 mt-2')}>
       {}
       {otherFiles.length > 0 && (
-        <div className="flex flex-wrap gap-2">
+        <div className={cn('flex flex-wrap', compact ? 'gap-1.5' : 'gap-2')}>
           {otherFiles.map((file, index) => (
             <div
               key={`file-${index}`}
-              className="inline-flex items-center gap-1.5 px-2.5 py-1 bg-muted/30 border border-border/30 rounded-xl typography-meta"
+              className={cn(
+                'inline-flex items-center bg-muted/30 border border-border/30 typography-meta',
+                compact ? 'gap-1 px-2 py-0.5 rounded-lg' : 'gap-1.5 px-2.5 py-1 rounded-xl'
+              )}
             >
               {getFileIcon(file.mime)}
-              <div className="overflow-hidden max-w-[200px]">
+              <div className={cn('overflow-hidden', compact ? 'max-w-[140px]' : 'max-w-[200px]')}>
                 <span className="truncate block" title={extractFilename(file.filename)}>
                   {extractFilename(file.filename)}
                 </span>
@@ -303,8 +354,8 @@ export const MessageFilesDisplay = memo(({ files, onShowPopup }: MessageFilesDis
 
       {}
       {imageFiles.length > 0 && (
-        <div className="overflow-x-auto -mx-1 px-1 py-1 scrollbar-thin">
-          <div className="flex gap-3 snap-x snap-mandatory">
+        <div className={cn('overflow-x-auto -mx-1 px-1 scrollbar-thin', compact ? 'py-0.5' : 'py-1')}>
+          <div className={cn('flex snap-x snap-mandatory', compact ? 'gap-2' : 'gap-3')}>
             {imageFiles.map((file, index) => {
     const filename = extractFilename(file.filename) || 'Image';
 
@@ -313,8 +364,13 @@ export const MessageFilesDisplay = memo(({ files, onShowPopup }: MessageFilesDis
                   <TooltipTrigger asChild>
                     <button
                       type="button"
-                      onClick={() => handleImageClick(file)}
-                      className="relative flex-none w-16 sm:w-20 md:w-24 aspect-square rounded-xl border border-border/40 bg-muted/10 overflow-hidden snap-start focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-offset-1 focus-visible:ring-primary"
+                      onClick={() => handleImageClick(index)}
+                      className={cn(
+                        'relative flex-none border border-border/40 bg-muted/10 overflow-hidden snap-start focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-offset-1 focus-visible:ring-primary',
+                        compact
+                          ? 'h-12 w-12 sm:h-14 sm:w-14 md:h-16 md:w-16 rounded-lg'
+                          : 'aspect-square w-16 sm:w-20 md:w-24 rounded-xl'
+                      )}
                       aria-label={filename}
                     >
                       {file.url ? (

packages/ui/src/components/chat/MessageList.tsx

@@ -8,6 +8,7 @@ import type { PermissionRequest } from '@/types/permission';
 import type { QuestionRequest } from '@/types/question';
 import type { AnimationHandlers, ContentChangeReason } from '@/hooks/useChatScrollManager';
 import { filterSyntheticParts } from '@/lib/messages/synthetic';
+import { detectTurns, type Turn } from './hooks/useTurnGrouping';
 import { TurnGroupingProvider, useMessageNeighbors, useTurnGroupingContextForMessage, useTurnGroupingContextStatic, useLastTurnMessageIds } from './contexts/TurnGroupingContext';
 
 interface ChatMessageEntry {
@@ -87,31 +88,103 @@ const DynamicMessageRow = React.memo<MessageRowProps>(({
 
 DynamicMessageRow.displayName = 'DynamicMessageRow';
 
-// Inner component that renders messages with access to context hooks
-const MessageListContent: React.FC<{
-    displayMessages: ChatMessageEntry[];
+interface TurnBlockProps {
+    turn: Turn;
     onMessageContentChange: (reason?: ContentChangeReason) => void;
     getAnimationHandlers: (messageId: string) => AnimationHandlers;
     scrollToBottom?: (options?: { instant?: boolean; force?: boolean }) => void;
-}> = ({ displayMessages, onMessageContentChange, getAnimationHandlers, scrollToBottom }) => {
+}
+
+const TurnBlock: React.FC<TurnBlockProps> = ({
+    turn,
+    onMessageContentChange,
+    getAnimationHandlers,
+    scrollToBottom,
+}) => {
     const lastTurnMessageIds = useLastTurnMessageIds();
+
+    const renderMessage = React.useCallback(
+        (message: ChatMessageEntry) => {
+            const role = (message.info as { clientRole?: string | null | undefined }).clientRole ?? message.info.role;
+            const isInLastTurn = role !== 'user' && lastTurnMessageIds.has(message.info.id);
+            const RowComponent = isInLastTurn ? DynamicMessageRow : StaticMessageRow;
+
+            return (
+                <RowComponent
+                    key={message.info.id}
+                    message={message}
+                    onContentChange={onMessageContentChange}
+                    animationHandlers={getAnimationHandlers(message.info.id)}
+                    scrollToBottom={scrollToBottom}
+                />
+            );
+        },
+        [getAnimationHandlers, lastTurnMessageIds, onMessageContentChange, scrollToBottom]
+    );
+
+    return (
+        <section className="relative w-full" data-turn-id={turn.turnId}>
+            <div className="sticky top-0 z-20 relative bg-[var(--surface-background)] [overflow-anchor:none]">
+                <div className="relative z-10">
+                    {renderMessage(turn.userMessage)}
+                </div>
+                <div
+                    aria-hidden="true"
+                    className="pointer-events-none absolute inset-x-0 top-full z-0 h-8 bg-gradient-to-b from-[var(--surface-background)] to-transparent"
+                />
+            </div>
+
+            <div className="relative z-0">
+                {turn.assistantMessages.map((message) => renderMessage(message))}
+            </div>
+        </section>
+    );
+};
+
+TurnBlock.displayName = 'TurnBlock';
+
+// Inner component that renders messages with access to context hooks
+const MessageListContent: React.FC<{
+    turns: Turn[];
+    ungroupedMessages: ChatMessageEntry[];
+    onMessageContentChange: (reason?: ContentChangeReason) => void;
+    getAnimationHandlers: (messageId: string) => AnimationHandlers;
+    scrollToBottom?: (options?: { instant?: boolean; force?: boolean }) => void;
+}> = ({ turns, ungroupedMessages, onMessageContentChange, getAnimationHandlers, scrollToBottom }) => {
+    const lastTurnMessageIds = useLastTurnMessageIds();
+
+    const renderUngroupedMessage = React.useCallback(
+        (message: ChatMessageEntry) => {
+            const role = (message.info as { clientRole?: string | null | undefined }).clientRole ?? message.info.role;
+            const isInLastTurn = role !== 'user' && lastTurnMessageIds.has(message.info.id);
+            const RowComponent = isInLastTurn ? DynamicMessageRow : StaticMessageRow;
+
+            return (
+                <RowComponent
+                    key={message.info.id}
+                    message={message}
+                    onContentChange={onMessageContentChange}
+                    animationHandlers={getAnimationHandlers(message.info.id)}
+                    scrollToBottom={scrollToBottom}
+                />
+            );
+        },
+        [getAnimationHandlers, lastTurnMessageIds, onMessageContentChange, scrollToBottom]
+    );
     
     return (
         <>
-            {displayMessages.map((message) => {
-                const isInLastTurn = lastTurnMessageIds.has(message.info.id);
-                const RowComponent = isInLastTurn ? DynamicMessageRow : StaticMessageRow;
-                
-                return (
-                    <RowComponent
-                        key={message.info.id}
-                        message={message}
-                        onContentChange={onMessageContentChange}
-                        animationHandlers={getAnimationHandlers(message.info.id)}
-                        scrollToBottom={scrollToBottom}
-                    />
-                );
-            })}
+            {ungroupedMessages.map((message) => renderUngroupedMessage(message))}
+
+            {turns.map((turn) => (
+                <TurnBlock
+                    key={turn.turnId}
+                    turn={turn}
+                    onMessageContentChange={onMessageContentChange}
+                    getAnimationHandlers={getAnimationHandlers}
+                    scrollToBottom={scrollToBottom}
+                />
+            ))}
         </>
     );
 };
@@ -161,6 +234,25 @@ const MessageList: React.FC<MessageListProps> = ({
             });
     }, [messages]);
 
+    const { turns, ungroupedMessages } = React.useMemo(() => {
+        const groupedTurns = detectTurns(displayMessages);
+        const groupedMessageIds = new Set<string>();
+
+        groupedTurns.forEach((turn) => {
+            groupedMessageIds.add(turn.userMessage.info.id);
+            turn.assistantMessages.forEach((message) => {
+                groupedMessageIds.add(message.info.id);
+            });
+        });
+
+        const ungrouped = displayMessages.filter((message) => !groupedMessageIds.has(message.info.id));
+
+        return {
+            turns: groupedTurns,
+            ungroupedMessages: ungrouped,
+        };
+    }, [displayMessages]);
+
     return (
         <TurnGroupingProvider messages={displayMessages}>
             <div>
@@ -183,7 +275,8 @@ const MessageList: React.FC<MessageListProps> = ({
                 )}
 
                 <MessageListContent
-                    displayMessages={displayMessages}
+                    turns={turns}
+                    ungroupedMessages={ungroupedMessages}
                     onMessageContentChange={onMessageContentChange}
                     getAnimationHandlers={getAnimationHandlers}
                     scrollToBottom={scrollToBottom}

packages/ui/src/components/chat/QueuedMessageChips.tsx

@@ -100,7 +100,6 @@ export const QueuedMessageChips = memo(({ onEditMessage }: QueuedMessageChipsPro
     return (
         <div className="pb-2">
             <div className="flex items-center flex-wrap gap-2 px-3 py-2 bg-muted/30 rounded-xl border border-border/30">
-                <span className="typography-meta text-muted-foreground font-medium">Queued:</span>
                 {queuedMessages.map((message) => (
                     <QueuedMessageChip
                         key={message.id}

packages/ui/src/components/chat/message/MessageBody.tsx

@@ -181,11 +181,19 @@ const UserMessageBody: React.FC<{
                     );
                 })}
             </div>
-            <MessageFilesDisplay files={parts} onShowPopup={onShowPopup} />
+            <MessageFilesDisplay files={parts} onShowPopup={onShowPopup} compact />
             {(canCopyMessage && hasCopyableText) || onRevert || onFork ? (
                 <div className={cn(
-                    "mt-1 flex items-center justify-end gap-2"
+                    "absolute top-full left-0 right-0 z-10 pt-5 group/user-actions"
                 )}>
+                    <div
+                        className={cn(
+                            "flex translate-x-5 items-center justify-end gap-1",
+                            isMobile
+                                ? "pointer-events-auto opacity-100"
+                                : "pointer-events-none opacity-0 transition-opacity duration-150 group-hover/message:pointer-events-auto group-hover/message:opacity-100 group-hover/user-actions:pointer-events-auto group-hover/user-actions:opacity-100"
+                        )}
+                    >
                     {onRevert && (
                         <Tooltip delayDuration={1000}>
                             <TooltipTrigger asChild>
@@ -193,7 +201,7 @@ const UserMessageBody: React.FC<{
                                     type="button"
                                     variant="ghost"
                                     size="icon"
-                                    className="h-8 w-8 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50"
+                                    className="h-6 w-6 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50"
                                     aria-label="Revert to this message"
                                     onPointerDown={(event) => event.stopPropagation()}
                                     onClick={(event) => {
@@ -201,7 +209,7 @@ const UserMessageBody: React.FC<{
                                         onRevert();
                                     }}
                                 >
-                                    <RiArrowGoBackLine className="h-3.5 w-3.5" />
+                                    <RiArrowGoBackLine className="h-3 w-3" />
                                 </Button>
                             </TooltipTrigger>
                             <TooltipContent sideOffset={6}>Revert from here</TooltipContent>
@@ -214,14 +222,14 @@ const UserMessageBody: React.FC<{
                                     type="button"
                                     variant="ghost"
                                     size="icon"
-                                    className="h-8 w-8 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50"
+                                    className="h-6 w-6 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50"
                                     onPointerDown={(event) => event.stopPropagation()}
                                     onClick={(event) => {
                                         event.stopPropagation();
                                         onFork();
                                     }}
                                 >
-                                    <RiGitBranchLine className="h-3.5 w-3.5" />
+                                    <RiGitBranchLine className="h-3 w-3" />
                                 </Button>
                             </TooltipTrigger>
                             <TooltipContent sideOffset={6}>Fork from here</TooltipContent>
@@ -235,7 +243,7 @@ const UserMessageBody: React.FC<{
                                     variant="ghost"
                                     size="icon"
                                     data-visible={copyHintVisible || isMessageCopied ? 'true' : undefined}
-                                    className="h-8 w-8 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50"
+                                    className="h-6 w-6 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50"
                                     aria-label="Copy message text"
                                     onPointerDown={(event) => event.stopPropagation()}
                                     onClick={handleCopyButtonClick}
@@ -247,15 +255,16 @@ const UserMessageBody: React.FC<{
                                     }}
                                 >
                                     {isMessageCopied ? (
-                                        <RiCheckLine className="h-3.5 w-3.5 text-[color:var(--status-success)]" />
+                                        <RiCheckLine className="h-3 w-3 text-[color:var(--status-success)]" />
                                     ) : (
-                                        <RiFileCopyLine className="h-3.5 w-3.5" />
+                                        <RiFileCopyLine className="h-3 w-3" />
                                     )}
                                 </Button>
                             </TooltipTrigger>
                             <TooltipContent sideOffset={6}>Copy message</TooltipContent>
                         </Tooltip>
                     )}
+                    </div>
                 </div>
             ) : null}
         </div>
@@ -872,7 +881,6 @@ const AssistantMessageBody: React.FC<Omit<MessageBodyProps, 'isUser'>> = ({
     const showErrorMessage = Boolean(errorMessage);
 
     const shouldShowFooter = isLastAssistantInTurn && hasTextContent && (hasStopFinish || Boolean(errorMessage));
-    const [isSummaryHovered, setIsSummaryHovered] = React.useState(false);
 
     const turnDurationText = React.useMemo(() => {
         if (!isLastAssistantInTurn || !hasStopFinish) return undefined;
@@ -884,6 +892,44 @@ const AssistantMessageBody: React.FC<Omit<MessageBodyProps, 'isUser'>> = ({
 
     const footerButtons = (
          <>
+              {onCopyMessage && (
+                  <Tooltip delayDuration={1000}>
+                      <TooltipTrigger asChild>
+                          <Button
+                              type="button"
+                              variant="ghost"
+                              size="icon"
+                              data-visible={copyHintVisible || isMessageCopied ? 'true' : undefined}
+                              className={cn(
+                                  'h-8 w-8 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50',
+                                  !hasCopyableText && 'opacity-50'
+                              )}
+                              disabled={!hasCopyableText}
+                              aria-label="Copy message text"
+                              aria-hidden={!hasCopyableText}
+                              onPointerDown={(event) => event.stopPropagation()}
+                              onClick={handleCopyButtonClick}
+                              onFocus={() => {
+                                  if (hasCopyableText) {
+                                      setCopyHintVisible(true);
+                                  }
+                              }}
+                              onBlur={() => {
+                                  if (!isMessageCopied) {
+                                      setCopyHintVisible(false);
+                                  }
+                              }}
+                          >
+                              {isMessageCopied ? (
+                                  <RiCheckLine className="h-3.5 w-3.5 text-[color:var(--status-success)]" />
+                              ) : (
+                                  <RiFileCopyLine className="h-3.5 w-3.5" />
+                              )}
+                          </Button>
+                      </TooltipTrigger>
+                      <TooltipContent sideOffset={6}>Copy answer</TooltipContent>
+                  </Tooltip>
+              )}
               <Tooltip delayDuration={1000}>
                   <TooltipTrigger asChild>
                       <Button
@@ -915,9 +961,9 @@ const AssistantMessageBody: React.FC<Omit<MessageBodyProps, 'isUser'>> = ({
                   <TooltipContent sideOffset={6}>Start new multi-run from this answer</TooltipContent>
               </Tooltip>
 
-             {showMessageTTSButtons && hasCopyableText && (
-                 <Tooltip delayDuration={1000}>
-                     <TooltipTrigger asChild>
+              {showMessageTTSButtons && hasCopyableText && (
+                  <Tooltip delayDuration={1000}>
+                      <TooltipTrigger asChild>
                          <Button
                              type="button"
                              variant="ghost"
@@ -937,49 +983,11 @@ const AssistantMessageBody: React.FC<Omit<MessageBodyProps, 'isUser'>> = ({
                              )}
                          </Button>
                      </TooltipTrigger>
-                      <TooltipContent sideOffset={6}>{readAloudTooltip}</TooltipContent>
-                  </Tooltip>
-              )}
-             {onCopyMessage && (
-                 <Tooltip delayDuration={1000}>
-                     <TooltipTrigger asChild>
-                         <Button
-                             type="button"
-                             variant="ghost"
-                             size="icon"
-                             data-visible={copyHintVisible || isMessageCopied ? 'true' : undefined}
-                             className={cn(
-                                 'h-8 w-8 text-muted-foreground bg-transparent hover:text-foreground hover:!bg-transparent active:!bg-transparent focus-visible:!bg-transparent focus-visible:ring-2 focus-visible:ring-primary/50',
-                                 !hasCopyableText && 'opacity-50'
-                             )}
-                             disabled={!hasCopyableText}
-                             aria-label="Copy message text"
-                             aria-hidden={!hasCopyableText}
-                             onPointerDown={(event) => event.stopPropagation()}
-                             onClick={handleCopyButtonClick}
-                             onFocus={() => {
-                                 if (hasCopyableText) {
-                                     setCopyHintVisible(true);
-                                 }
-                             }}
-                             onBlur={() => {
-                                 if (!isMessageCopied) {
-                                     setCopyHintVisible(false);
-                                 }
-                             }}
-                         >
-                             {isMessageCopied ? (
-                                 <RiCheckLine className="h-3.5 w-3.5 text-[color:var(--status-success)]" />
-                             ) : (
-                                 <RiFileCopyLine className="h-3.5 w-3.5" />
-                             )}
-                         </Button>
-                     </TooltipTrigger>
-                     <TooltipContent sideOffset={6}>Copy answer</TooltipContent>
-                 </Tooltip>
-             )}
-         </>
-     );
+                       <TooltipContent sideOffset={6}>{readAloudTooltip}</TooltipContent>
+                   </Tooltip>
+               )}
+          </>
+      );
  
       return (
 
@@ -1011,26 +1019,19 @@ const AssistantMessageBody: React.FC<Omit<MessageBodyProps, 'isUser'>> = ({
                         <FadeInOnReveal key="summary-body">
                             <div
                                 className="group/assistant-text relative break-words"
-                                onMouseEnter={() => setIsSummaryHovered(true)}
-                                onMouseLeave={() => setIsSummaryHovered(false)}
                             >
                                 <SimpleMarkdownRenderer content={summaryBody} />
                                 {shouldShowFooter && (
-                                    <div className="mt-2 mb-1 flex items-center justify-between gap-2">
+                                    <div className="mt-2 mb-1 flex items-center justify-start gap-1.5">
+                                        <div className="flex items-center gap-1.5">
+                                            {footerButtons}
+                                        </div>
                                         {turnDurationText ? (
                                             <span className="text-sm text-muted-foreground/60 tabular-nums flex items-center gap-1">
                                                 <RiHourglassLine className="h-3.5 w-3.5" />
                                                 {turnDurationText}
                                             </span>
-                                        ) : <span />}
-                                        <div
-                                            className={cn(
-                                                "flex items-center gap-2 opacity-0 pointer-events-none transition-opacity duration-150 focus-within:opacity-100 focus-within:pointer-events-auto",
-                                                isSummaryHovered && "opacity-100 pointer-events-auto",
-                                            )}
-                                        >
-                                            {footerButtons}
-                                        </div>
+                                        ) : null}
                                     </div>
                                 )}
                             </div>
@@ -1039,16 +1040,16 @@ const AssistantMessageBody: React.FC<Omit<MessageBodyProps, 'isUser'>> = ({
                 </div>
                 <MessageFilesDisplay files={parts} onShowPopup={onShowPopup} />
                 {!showSummaryBody && shouldShowFooter && (
-                    <div className="mt-2 mb-1 flex items-center justify-between gap-2">
+                    <div className="mt-2 mb-1 flex items-center justify-start gap-1.5">
+                        <div className="flex items-center gap-1.5">
+                            {footerButtons}
+                        </div>
                         {turnDurationText ? (
                             <span className="text-sm text-muted-foreground/60 tabular-nums flex items-center gap-1">
                                 <RiHourglassLine className="h-3.5 w-3.5" />
                                 {turnDurationText}
                             </span>
-                        ) : <span />}
-                        <div className="flex items-center gap-2 opacity-0 pointer-events-none transition-opacity duration-150 group-hover/message:opacity-100 group-hover/message:pointer-events-auto focus-within:opacity-100 focus-within:pointer-events-auto">
-                            {footerButtons}
-                        </div>
+                        ) : null}
                     </div>
                 )}
 

packages/ui/src/components/chat/message/ToolOutputDialog.tsx

@@ -1,7 +1,8 @@
 import React from 'react';
 import { Dialog, DialogContent } from '@/components/ui/dialog';
-import { RiBrainAi3Line, RiFileImageLine, RiFileList2Line, RiFilePdfLine, RiFileSearchLine, RiFolder6Line, RiGitBranchLine, RiGlobalLine, RiListCheck3, RiPencilAiLine, RiSearchLine, RiTaskLine, RiTerminalBoxLine, RiToolsLine } from '@remixicon/react';
+import { RiArrowLeftSLine, RiArrowRightSLine, RiBrainAi3Line, RiCloseLine, RiFileImageLine, RiFileList2Line, RiFilePdfLine, RiFileSearchLine, RiFolder6Line, RiGitBranchLine, RiGlobalLine, RiListCheck3, RiPencilAiLine, RiSearchLine, RiTaskLine, RiTerminalBoxLine, RiToolsLine } from '@remixicon/react';
 import { Prism as SyntaxHighlighter } from 'react-syntax-highlighter';
+import { createPortal } from 'react-dom';
 
 import { cn } from '@/lib/utils';
 import { SimpleMarkdownRenderer } from '../MarkdownRenderer';
@@ -81,9 +82,285 @@ const getToolIcon = (toolName: string) => {
     return <RiToolsLine className={iconClass} />;
 };
 
+const IMAGE_PREVIEW_ANIMATION_MS = 150;
+
+const ImagePreviewDialog: React.FC<{
+    popup: ToolPopupContent;
+    onOpenChange: (open: boolean) => void;
+    isMobile: boolean;
+}> = ({ popup, onOpenChange, isMobile }) => {
+    const gallery = React.useMemo(() => {
+        const baseImage = popup.image;
+        if (!baseImage) return [] as Array<{ url: string; mimeType?: string; filename?: string; size?: number }>;
+        const fromPopup = Array.isArray(baseImage.gallery)
+            ? baseImage.gallery.filter((item): item is { url: string; mimeType?: string; filename?: string; size?: number } => Boolean(item?.url))
+            : [];
+
+        if (fromPopup.length > 0) {
+            return fromPopup;
+        }
+
+        return [{
+            url: baseImage.url,
+            mimeType: baseImage.mimeType,
+            filename: baseImage.filename,
+            size: baseImage.size,
+        }];
+    }, [popup.image]);
+
+    const [currentIndex, setCurrentIndex] = React.useState(0);
+    const [imageNaturalSize, setImageNaturalSize] = React.useState<{ width: number; height: number } | null>(null);
+    const [isRendered, setIsRendered] = React.useState(popup.open);
+    const [isVisible, setIsVisible] = React.useState(popup.open);
+    const [isTransitioning, setIsTransitioning] = React.useState(false);
+    const [viewport, setViewport] = React.useState<{ width: number; height: number }>({
+        width: typeof window !== 'undefined' ? window.innerWidth : 0,
+        height: typeof window !== 'undefined' ? window.innerHeight : 0,
+    });
+
+    React.useEffect(() => {
+        if (!popup.open || gallery.length === 0) {
+            return;
+        }
+
+        const requestedIndex = typeof popup.image?.index === 'number' ? popup.image.index : -1;
+        if (requestedIndex >= 0 && requestedIndex < gallery.length) {
+            setCurrentIndex(requestedIndex);
+            return;
+        }
+
+        const matchingIndex = popup.image?.url
+            ? gallery.findIndex((item) => item.url === popup.image?.url)
+            : -1;
+        setCurrentIndex(matchingIndex >= 0 ? matchingIndex : 0);
+    }, [gallery, popup.image?.index, popup.image?.url, popup.open]);
+
+    const currentImage = gallery[currentIndex] ?? gallery[0] ?? popup.image;
+    const imageTitle = currentImage?.filename || popup.title || 'Image preview';
+    const hasMultipleImages = gallery.length > 1;
+
+    const showPrevious = React.useCallback(() => {
+        if (gallery.length <= 1) return;
+        setCurrentIndex((prev) => (prev - 1 + gallery.length) % gallery.length);
+    }, [gallery.length]);
+
+    const showNext = React.useCallback(() => {
+        if (gallery.length <= 1) return;
+        setCurrentIndex((prev) => (prev + 1) % gallery.length);
+    }, [gallery.length]);
+
+    React.useEffect(() => {
+        if (popup.open) {
+            setIsRendered(true);
+            setIsTransitioning(true);
+            if (typeof window === 'undefined') {
+                setIsVisible(true);
+                return;
+            }
+
+            const raf = window.requestAnimationFrame(() => {
+                setIsVisible(true);
+            });
+
+            const doneId = window.setTimeout(() => {
+                setIsTransitioning(false);
+            }, IMAGE_PREVIEW_ANIMATION_MS);
+
+            return () => {
+                window.cancelAnimationFrame(raf);
+                window.clearTimeout(doneId);
+            };
+        }
+
+        setIsVisible(false);
+        setIsTransitioning(true);
+        if (typeof window === 'undefined') {
+            setIsRendered(false);
+            return;
+        }
+
+        const timeoutId = window.setTimeout(() => {
+            setIsRendered(false);
+            setIsTransitioning(false);
+        }, IMAGE_PREVIEW_ANIMATION_MS);
+
+        return () => {
+            window.clearTimeout(timeoutId);
+        };
+    }, [popup.open]);
+
+    React.useEffect(() => {
+        if (!popup.open) {
+            return;
+        }
+
+        const onKeyDown = (event: KeyboardEvent) => {
+            if (event.key === 'Escape') {
+                onOpenChange(false);
+                return;
+            }
+
+            if (event.key === 'ArrowLeft' && hasMultipleImages) {
+                event.preventDefault();
+                showPrevious();
+                return;
+            }
+
+            if (event.key === 'ArrowRight' && hasMultipleImages) {
+                event.preventDefault();
+                showNext();
+            }
+        };
+
+        window.addEventListener('keydown', onKeyDown);
+        return () => {
+            window.removeEventListener('keydown', onKeyDown);
+        };
+    }, [hasMultipleImages, onOpenChange, popup.open, showNext, showPrevious]);
+
+    React.useEffect(() => {
+        if (!popup.open || typeof window === 'undefined') {
+            return;
+        }
+
+        const onResize = () => {
+            setViewport({ width: window.innerWidth, height: window.innerHeight });
+        };
+
+        onResize();
+        window.addEventListener('resize', onResize);
+        return () => {
+            window.removeEventListener('resize', onResize);
+        };
+    }, [popup.open]);
+
+    React.useEffect(() => {
+        setImageNaturalSize(null);
+    }, [currentImage?.url]);
+
+    const imageDisplaySize = React.useMemo(() => {
+        const maxWidth = Math.max(160, viewport.width * (isMobile ? 0.86 : 0.75));
+        const maxHeight = Math.max(160, viewport.height * (isMobile ? 0.72 : 0.75));
+
+        if (!imageNaturalSize) {
+            return {
+                width: Math.round(maxWidth),
+                height: Math.round(maxHeight),
+            };
+        }
+
+        const widthScale = maxWidth / imageNaturalSize.width;
+        const heightScale = maxHeight / imageNaturalSize.height;
+        const scale = Math.min(widthScale, heightScale);
+
+        return {
+            width: Math.max(1, Math.round(imageNaturalSize.width * scale)),
+            height: Math.max(1, Math.round(imageNaturalSize.height * scale)),
+        };
+    }, [imageNaturalSize, isMobile, viewport.height, viewport.width]);
+
+    if (!isRendered || !currentImage || typeof document === 'undefined') {
+        return null;
+    }
+
+    const content = (
+        <div className={cn('fixed inset-0 z-50', popup.open ? 'pointer-events-auto' : 'pointer-events-none')}>
+            <div
+                aria-hidden="true"
+                className={cn(
+                    'absolute inset-0 bg-black/25 backdrop-blur-md',
+                    isTransitioning && 'transition-opacity duration-150 ease-out',
+                    isVisible ? 'opacity-100' : 'opacity-0'
+                )}
+                onMouseDown={() => onOpenChange(false)}
+            />
+
+            {hasMultipleImages && (
+                <>
+                    <button
+                        type="button"
+                        onMouseDown={(event) => event.stopPropagation()}
+                        onClick={showPrevious}
+                        className="absolute left-3 top-1/2 -translate-y-1/2 z-10 h-10 w-10 flex items-center justify-center rounded-full bg-black/25 text-foreground/90 backdrop-blur-sm hover:bg-black/35 focus:outline-none focus:ring-2 focus:ring-primary/60"
+                        aria-label="Previous image"
+                    >
+                        <RiArrowLeftSLine className="h-6 w-6" />
+                    </button>
+                    <button
+                        type="button"
+                        onMouseDown={(event) => event.stopPropagation()}
+                        onClick={showNext}
+                        className="absolute right-3 top-1/2 -translate-y-1/2 z-10 h-10 w-10 flex items-center justify-center rounded-full bg-black/25 text-foreground/90 backdrop-blur-sm hover:bg-black/35 focus:outline-none focus:ring-2 focus:ring-primary/60"
+                        aria-label="Next image"
+                    >
+                        <RiArrowRightSLine className="h-6 w-6" />
+                    </button>
+                </>
+            )}
+
+            <div
+                className={cn(
+                    'absolute inset-0 flex items-center justify-center pointer-events-none',
+                    isMobile ? 'p-2.5' : 'p-4'
+                )}
+            >
+                <div
+                    className={cn(
+                        'pointer-events-auto flex flex-col gap-2',
+                        isTransitioning && 'transition-opacity duration-150 ease-out',
+                        isVisible ? 'opacity-100' : 'opacity-0'
+                    )}
+                    style={{ width: `${imageDisplaySize.width}px` }}
+                >
+                    <div className="flex items-center justify-between gap-2">
+                        <div className="min-w-0 flex-1 text-foreground typography-ui-header font-semibold truncate" title={imageTitle}>
+                            {imageTitle}
+                        </div>
+                        <button
+                            type="button"
+                            className="h-8 w-8 flex items-center justify-center rounded-lg text-muted-foreground/80 hover:text-foreground focus:outline-none focus:ring-2 focus:ring-primary/60"
+                            onClick={() => onOpenChange(false)}
+                            aria-label="Close image preview"
+                        >
+                            <RiCloseLine className="h-4 w-4" />
+                        </button>
+                    </div>
+
+                    <img
+                        src={currentImage.url}
+                        alt={imageTitle}
+                        className="block object-contain"
+                        style={{ width: `${imageDisplaySize.width}px`, height: `${imageDisplaySize.height}px` }}
+                        loading="lazy"
+                        onLoad={(event) => {
+                            const element = event.currentTarget;
+                            const width = element.naturalWidth;
+                            const height = element.naturalHeight;
+                            if (width > 0 && height > 0) {
+                                setImageNaturalSize((previous) => {
+                                    if (previous && previous.width === width && previous.height === height) {
+                                        return previous;
+                                    }
+                                    return { width, height };
+                                });
+                            }
+                        }}
+                    />
+                </div>
+            </div>
+        </div>
+    );
+
+    return createPortal(content, document.body);
+};
+
 const ToolOutputDialog: React.FC<ToolOutputDialogProps> = ({ popup, onOpenChange, syntaxTheme, isMobile }) => {
     const [diffViewMode, setDiffViewMode] = React.useState<DiffViewMode>(isMobile ? 'unified' : 'side-by-side');
 
+    if (popup.image) {
+        return <ImagePreviewDialog popup={popup} onOpenChange={onOpenChange} isMobile={isMobile} />;
+    }
+
     return (
         <Dialog open={popup.open} onOpenChange={onOpenChange}>
             <DialogContent
@@ -385,24 +662,6 @@ const ToolOutputDialog: React.FC<ToolOutputDialogProps> = ({ popup, onOpenChange
                                 ))}
                             </div>
                         ) : null
-                    ) : popup.image ? (
-                        <div className="p-4">
-                            <div className="flex flex-col items-center gap-3">
-                                <div className="max-h-[70vh] overflow-hidden rounded-2xl border border-border/40 bg-muted/10">
-                                    <img
-                                        src={popup.image.url}
-                                        alt={popup.image.filename || popup.title || 'Image preview'}
-                                        className="block h-full max-h-[70vh] w-auto max-w-full object-contain"
-                                        loading="lazy"
-                                    />
-                                </div>
-                                {popup.image.filename && (
-                                    <span className="typography-meta text-muted-foreground text-center">
-                                        {popup.image.filename}
-                                    </span>
-                                )}
-                            </div>
-                        </div>
                     ) : popup.content ? (
                         <div className="p-4">
                             {(() => {

packages/ui/src/components/chat/message/parts/UserTextPart.tsx

@@ -19,20 +19,45 @@ const buildMentionUrl = (name: string): string => {
 };
 
 const UserTextPart: React.FC<UserTextPartProps> = ({ part, messageId, agentMention }) => {
+    const CLAMP_LINES = 2;
     const partWithText = part as PartWithText;
     const rawText = partWithText.text;
     const textContent = typeof rawText === 'string' ? rawText : partWithText.content || partWithText.value || '';
 
     const [isExpanded, setIsExpanded] = React.useState(false);
     const [isTruncated, setIsTruncated] = React.useState(false);
+    const [collapseZoneHeight, setCollapseZoneHeight] = React.useState<number>(0);
     const textRef = React.useRef<HTMLDivElement>(null);
 
+    const hasActiveSelectionInElement = React.useCallback((element: HTMLElement): boolean => {
+        if (typeof window === 'undefined') {
+            return false;
+        }
+
+        const selection = window.getSelection();
+        if (!selection || selection.isCollapsed || selection.rangeCount === 0) {
+            return false;
+        }
+
+        const range = selection.getRangeAt(0);
+        return element.contains(range.startContainer) || element.contains(range.endContainer);
+    }, []);
+
     React.useEffect(() => {
         const el = textRef.current;
-        if (!el || isExpanded) return;
+        if (!el) return;
 
         const checkTruncation = () => {
-            setIsTruncated(el.scrollHeight > el.clientHeight);
+            if (!isExpanded) {
+                setIsTruncated(el.scrollHeight > el.clientHeight);
+            }
+
+            const styles = window.getComputedStyle(el);
+            const lineHeight = Number.parseFloat(styles.lineHeight);
+            const fontSize = Number.parseFloat(styles.fontSize);
+            const fallbackLineHeight = Number.isFinite(fontSize) ? fontSize * 1.4 : 20;
+            const resolvedLineHeight = Number.isFinite(lineHeight) ? lineHeight : fallbackLineHeight;
+            setCollapseZoneHeight(Math.max(1, Math.round(resolvedLineHeight * CLAMP_LINES)));
         };
 
         checkTruncation();
@@ -43,11 +68,28 @@ const UserTextPart: React.FC<UserTextPartProps> = ({ part, messageId, agentMenti
         return () => resizeObserver.disconnect();
     }, [textContent, isExpanded]);
 
-    const handleClick = React.useCallback(() => {
-        if (isTruncated || isExpanded) {
-            setIsExpanded((prev) => !prev);
+    const handleClick = React.useCallback((event: React.MouseEvent<HTMLDivElement>) => {
+        const element = textRef.current;
+        if (!element) {
+            return;
         }
-    }, [isTruncated, isExpanded]);
+
+        if (hasActiveSelectionInElement(element)) {
+            return;
+        }
+
+        if (!isExpanded) {
+            if (isTruncated) {
+                setIsExpanded(true);
+            }
+            return;
+        }
+
+        const clickY = event.clientY - element.getBoundingClientRect().top;
+        if (clickY <= collapseZoneHeight) {
+            setIsExpanded(false);
+        }
+    }, [collapseZoneHeight, hasActiveSelectionInElement, isExpanded, isTruncated]);
 
     if (!textContent || textContent.trim().length === 0) {
         return null;
@@ -79,17 +121,18 @@ const UserTextPart: React.FC<UserTextPartProps> = ({ part, messageId, agentMenti
     };
 
     return (
-        <div
-            className={cn(
-                "break-words whitespace-pre-wrap font-sans typography-markdown",
-                !isExpanded && "line-clamp-3",
-                (isTruncated || isExpanded) && "cursor-pointer"
-            )}
-            ref={textRef}
-            onClick={handleClick}
-            key={part.id || `${messageId}-user-text`}
-        >
-            {renderContent()}
+        <div className="relative" key={part.id || `${messageId}-user-text`}>
+            <div
+                className={cn(
+                    "break-words whitespace-pre-wrap font-sans typography-markdown",
+                    !isExpanded && "line-clamp-2",
+                    isTruncated && !isExpanded && "cursor-pointer"
+                )}
+                ref={textRef}
+                onClick={handleClick}
+            >
+                {renderContent()}
+            </div>
         </div>
     );
 };

packages/ui/src/components/chat/message/types.ts

@@ -20,5 +20,12 @@ export interface ToolPopupContent {
         mimeType?: string;
         filename?: string;
         size?: number;
+        gallery?: Array<{
+            url: string;
+            mimeType?: string;
+            filename?: string;
+            size?: number;
+        }>;
+        index?: number;
     };
 }

packages/ui/src/components/layout/BottomTerminalDock.tsx

@@ -1,5 +1,5 @@
 import React from 'react';
-import { RiFullscreenExitLine, RiFullscreenLine } from '@remixicon/react';
+import { RiCloseLine, RiFullscreenExitLine, RiFullscreenLine } from '@remixicon/react';
 import { cn } from '@/lib/utils';
 import { useUIStore } from '@/stores/useUIStore';
 
@@ -157,15 +157,26 @@ export const BottomTerminalDock: React.FC<BottomTerminalDockProps> = ({ isOpen,
       )}
 
       {isOpen && (
-        <button
-          type="button"
-          onClick={toggleFullscreen}
-          className="absolute right-2 top-2 z-30 inline-flex h-8 w-8 items-center justify-center rounded-md text-[var(--surface-muted-foreground)] transition-colors hover:bg-[var(--interactive-hover)] hover:text-[var(--surface-foreground)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-primary/50"
-          title={isFullscreen ? 'Restore terminal panel height' : 'Expand terminal panel'}
-          aria-label={isFullscreen ? 'Restore terminal panel height' : 'Expand terminal panel'}
-        >
-          {isFullscreen ? <RiFullscreenExitLine className="h-5 w-5" /> : <RiFullscreenLine className="h-5 w-5" />}
-        </button>
+        <div className="absolute right-2 top-2 z-30 inline-flex items-center gap-1">
+          <button
+            type="button"
+            onClick={toggleFullscreen}
+            className="inline-flex h-8 w-8 items-center justify-center rounded-md text-[var(--surface-muted-foreground)] transition-colors hover:bg-[var(--interactive-hover)] hover:text-[var(--surface-foreground)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-primary/50"
+            title={isFullscreen ? 'Restore terminal panel height' : 'Expand terminal panel'}
+            aria-label={isFullscreen ? 'Restore terminal panel height' : 'Expand terminal panel'}
+          >
+            {isFullscreen ? <RiFullscreenExitLine className="h-5 w-5" /> : <RiFullscreenLine className="h-5 w-5" />}
+          </button>
+          <button
+            type="button"
+            onClick={() => setBottomTerminalOpen(false)}
+            className="inline-flex h-8 w-8 items-center justify-center rounded-md text-[var(--surface-muted-foreground)] transition-colors hover:bg-[var(--interactive-hover)] hover:text-[var(--surface-foreground)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-primary/50"
+            title="Close terminal panel"
+            aria-label="Close terminal panel"
+          >
+            <RiCloseLine className="h-6 w-6" />
+          </button>
+        </div>
       )}
 
       <div

packages/ui/src/components/layout/Header.tsx

@@ -882,19 +882,23 @@ export const Header: React.FC = () => {
                 <DropdownMenuTrigger asChild>
                   <button
                     type="button"
-                    aria-label={`Open instance, usage and MCP (current: ${currentInstanceLabel})`}
+                    aria-label={isDesktopApp
+                      ? `Open instance, usage and MCP (current: ${currentInstanceLabel})`
+                      : 'Open services, usage and MCP'}
                     className={cn(
                       headerIconButtonClass,
-                      'w-auto max-w-[14rem] justify-start gap-1.5 px-2.5'
+                      isDesktopApp
+                        ? 'w-auto max-w-[14rem] justify-start gap-1.5 px-2.5'
+                        : 'h-9 w-9'
                     )}
                   >
                     <RiStackLine className="h-5 w-5" />
-                    <span className="truncate text-base font-normal">{currentInstanceLabel}</span>
+                    {isDesktopApp && <span className="truncate text-base font-normal">{currentInstanceLabel}</span>}
                   </button>
                 </DropdownMenuTrigger>
               </TooltipTrigger>
               <TooltipContent>
-                <p>Current instance: {currentInstanceLabel}</p>
+                <p>{isDesktopApp ? `Current instance: ${currentInstanceLabel}` : 'Services'}</p>
               </TooltipContent>
             </Tooltip>
             <DropdownMenuContent

packages/ui/src/components/layout/VSCodeLayout.tsx

@@ -69,7 +69,15 @@ export const VSCodeLayout: React.FC = () => {
 
   const hasAppliedInitialSession = React.useRef(false);
 
-  const [currentView, setCurrentView] = React.useState<VSCodeView>('sessions');
+  const bootDraftOpen = React.useMemo(() => {
+    try {
+      return Boolean(useSessionStore.getState().newSessionDraft?.open);
+    } catch {
+      return false;
+    }
+  }, []);
+
+  const [currentView, setCurrentView] = React.useState<VSCodeView>(() => (bootDraftOpen ? 'chat' : 'sessions'));
   const [containerWidth, setContainerWidth] = React.useState<number>(0);
   const containerRef = React.useRef<HTMLDivElement>(null);
   const currentSessionId = useSessionStore((state) => state.currentSessionId);

packages/ui/src/components/session/SessionSidebar.tsx

@@ -632,6 +632,7 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
   const sessions = useSessionStore((state) => state.sessions);
   const sessionsByDirectory = useSessionStore((state) => state.sessionsByDirectory);
   const currentSessionId = useSessionStore((state) => state.currentSessionId);
+  const newSessionDraftOpen = useSessionStore((state) => Boolean(state.newSessionDraft?.open));
   const setCurrentSession = useSessionStore((state) => state.setCurrentSession);
   const updateSessionTitle = useSessionStore((state) => state.updateSessionTitle);
   const shareSession = useSessionStore((state) => state.shareSession);
@@ -882,8 +883,11 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
         setSessionSwitcherOpen(false);
       }
 
-      if (!allowReselect && sessionId === currentSessionId) {
-        onSessionSelected?.(sessionId);
+      // Always return early if same session is selected to avoid unnecessary store operations
+      if (sessionId === currentSessionId) {
+        if (!allowReselect) {
+          onSessionSelected?.(sessionId);
+        }
         return;
       }
       setCurrentSession(sessionId);
@@ -1458,6 +1462,11 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
 
   const previousActiveProjectRef = React.useRef<string | null>(null);
   React.useLayoutEffect(() => {
+    // While a new session draft is open, keep the sidebar from auto-selecting remembered/fallback sessions.
+    // This is especially important in VS Code where the sidebar view is frequently mounted/unmounted.
+    if (newSessionDraftOpen) {
+      return;
+    }
     if (!activeProjectId || previousActiveProjectRef.current === activeProjectId) {
       return;
     }
@@ -1467,6 +1476,21 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
     }
     previousActiveProjectRef.current = activeProjectId;
     const projectMap = projectSessionMeta.metaByProject.get(activeProjectId);
+
+    // If we already have an active session that belongs to this project (eg user just selected it,
+    // or sidebar remounted after "back"), do NOT override it with remembered/fallback session.
+    if (currentSessionId && projectMap && projectMap.has(currentSessionId)) {
+      setActiveSessionByProject((prev) => {
+        if (prev.get(activeProjectId) === currentSessionId) {
+          return prev;
+        }
+        const next = new Map(prev);
+        next.set(activeProjectId, currentSessionId);
+        return next;
+      });
+      return;
+    }
+
     if (!projectMap || projectMap.size === 0) {
       setActiveMainTab('chat');
       if (mobileVariant) {
@@ -1492,6 +1516,7 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
     activeSessionByProject,
     currentSessionId,
     handleSessionSelect,
+    newSessionDraftOpen,
     mobileVariant,
     openNewSessionDraft,
     projectSections,
@@ -1967,7 +1992,7 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
   );
 
   const renderGroupSessions = React.useCallback(
-    (group: SessionGroup, groupKey: string, projectId?: string | null) => {
+    (group: SessionGroup, groupKey: string, projectId?: string | null, hideGroupLabel?: boolean) => {
       const isExpanded = expandedSessionGroups.has(groupKey);
       const isCollapsed = collapsedGroups.has(groupKey);
       const maxVisible = hideDirectoryControls ? 10 : 5;
@@ -1997,11 +2022,49 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
           && normalizedGroupDirectory === currentSessionDirectory,
       );
 
+      // VS Code sessions list uses a separate header (Agent Manager / New Session).
+      // When the caller requests a flat list (hideGroupLabel), omit the per-group header entirely.
+      if (hideGroupLabel) {
+        return (
+          <div className="oc-group">
+            <div className="oc-group-body pb-3">
+              {visibleSessions.map((node) => renderSessionNode(node, 0, group.directory, projectId))}
+              {totalSessions === 0 ? (
+                <div className="py-1 text-left typography-micro text-muted-foreground">
+                  No sessions in this workspace yet.
+                </div>
+              ) : null}
+              {remainingCount > 0 && !isExpanded ? (
+                <button
+                  type="button"
+                  onClick={() => toggleGroupSessionLimit(groupKey)}
+                  className="mt-0.5 flex items-center justify-start rounded-md px-1.5 py-0.5 text-left text-xs text-muted-foreground/70 leading-tight hover:text-foreground hover:underline"
+                >
+                  Show {remainingCount} more {remainingCount === 1 ? 'session' : 'sessions'}
+                </button>
+              ) : null}
+              {isExpanded && totalSessions > maxVisible ? (
+                <button
+                  type="button"
+                  onClick={() => toggleGroupSessionLimit(groupKey)}
+                  className="mt-0.5 flex items-center justify-start rounded-md px-1.5 py-0.5 text-left text-xs text-muted-foreground/70 leading-tight hover:text-foreground hover:underline"
+                >
+                  Show fewer sessions
+                </button>
+              ) : null}
+            </div>
+          </div>
+        );
+      }
+
       return (
         <div className="oc-group">
           <div
-            className="group/gh flex items-center justify-between gap-2 py-1 min-w-0 rounded-sm hover:bg-interactive-hover/50 cursor-pointer"
-            onClick={() => {
+            className={cn(
+              "group/gh flex items-center justify-between gap-2 py-1 min-w-0 rounded-sm",
+              !hideGroupLabel && "hover:bg-interactive-hover/50 cursor-pointer"
+            )}
+            onClick={!hideGroupLabel ? () => {
               setCollapsedGroups((prev) => {
                 const next = new Set(prev);
                 if (next.has(groupKey)) {
@@ -2011,10 +2074,10 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
                 }
                 return next;
               });
-            }}
-            role="button"
-            tabIndex={0}
-            onKeyDown={(event) => {
+            } : undefined}
+            role={!hideGroupLabel ? "button" : undefined}
+            tabIndex={!hideGroupLabel ? 0 : undefined}
+            onKeyDown={!hideGroupLabel ? (event) => {
               if (event.key === 'Enter' || event.key === ' ') {
                 event.preventDefault();
                 setCollapsedGroups((prev) => {
@@ -2027,29 +2090,31 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
                   return next;
                 });
               }
-            }}
-            aria-label={isCollapsed ? `Expand ${group.label}` : `Collapse ${group.label}`}
+            } : undefined}
+            aria-label={!hideGroupLabel ? (isCollapsed ? `Expand ${group.label}` : `Collapse ${group.label}`) : undefined}
           >
-            <div className="min-w-0 flex items-center gap-1.5 px-0">
-              {isCollapsed ? (
-                <RiArrowRightSLine className="h-3.5 w-3.5 flex-shrink-0 text-muted-foreground" />
-              ) : (
-                <RiArrowDownSLine className="h-3.5 w-3.5 flex-shrink-0 text-muted-foreground" />
-              )}
-              {!group.isMain || isGitProject ? (
-                <RiGitBranchLine className="h-3.5 w-3.5 flex-shrink-0 text-muted-foreground" />
-              ) : null}
-              <div className="min-w-0 flex flex-col justify-center">
-                <p className={cn('text-[15px] font-semibold truncate', isActiveGroup ? 'text-primary' : 'text-muted-foreground')}>
-                  {group.label}
-                </p>
-                {showBranchSubtitle ? (
-                  <span className="text-[10px] sm:text-[11px] text-muted-foreground/80 truncate leading-tight">
-                    {group.branch}
-                  </span>
+            {!hideGroupLabel ? (
+              <div className="min-w-0 flex items-center gap-1.5 px-0">
+                {isCollapsed ? (
+                  <RiArrowRightSLine className="h-3.5 w-3.5 flex-shrink-0 text-muted-foreground" />
+                ) : (
+                  <RiArrowDownSLine className="h-3.5 w-3.5 flex-shrink-0 text-muted-foreground" />
+                )}
+                {!group.isMain || isGitProject ? (
+                  <RiGitBranchLine className="h-3.5 w-3.5 flex-shrink-0 text-muted-foreground" />
                 ) : null}
+                <div className="min-w-0 flex flex-col justify-center">
+                  <p className={cn('text-[15px] font-semibold truncate', isActiveGroup ? 'text-primary' : 'text-muted-foreground')}>
+                    {group.label}
+                  </p>
+                  {showBranchSubtitle ? (
+                    <span className="text-[10px] sm:text-[11px] text-muted-foreground/80 truncate leading-tight">
+                      {group.branch}
+                    </span>
+                  ) : null}
+                </div>
               </div>
-            </div>
+            ) : <div />}
             {group.directory ? (
               <div className="flex items-center gap-1 px-0.5">
                 {!group.isMain && group.worktree ? (
@@ -2404,7 +2469,8 @@ export const SessionSidebar: React.FC<SessionSidebarProps> = ({
                 );
               }
               const groupKey = `${activeSection.project.id}:${group.id}`;
-              return renderGroupSessions(group, groupKey, activeSection.project.id);
+              // In VS Code mode with showOnlyMainWorkspace, hide the group header to show a flat session list
+              return renderGroupSessions(group, groupKey, activeSection.project.id, showOnlyMainWorkspace);
             })()}
           </div>
         ) : (

packages/ui/src/components/ui/text.tsx

@@ -13,13 +13,13 @@ const variants = [
   {
     variant: "shine",
     component: ({ children, className, ...props }) => (
-      <motion.span
-        {...props}
-        className={cn(
-          "bg-[linear-gradient(110deg,#bfbfbf,35%,#000,50%,#bfbfbf,75%,#bfbfbf)] dark:bg-[linear-gradient(110deg,#404040,35%,#fff,50%,#404040,75%,#404040)]",
-          "bg-[length:200%_100%] bg-clip-text text-transparent",
-          className
-        )}
+        <motion.span
+          {...props}
+          className={cn(
+            "bg-[linear-gradient(110deg,color-mix(in_srgb,var(--surface-muted-foreground)_45%,transparent),35%,var(--surface-foreground),50%,color-mix(in_srgb,var(--surface-muted-foreground)_45%,transparent),75%,color-mix(in_srgb,var(--surface-muted-foreground)_45%,transparent))]",
+            "bg-[length:200%_100%] bg-clip-text text-transparent",
+            className
+          )}
         initial={{ backgroundPosition: "200% 0" }}
         animate={{ backgroundPosition: "-200% 0" }}
         transition={{

packages/ui/src/hooks/useChatScrollManager.ts

@@ -25,7 +25,6 @@ interface SessionMemoryState {
     isZombie?: boolean;
 }
 
-
 interface UseChatScrollManagerOptions {
     currentSessionId: string | null;
     sessionMessages: ChatMessageRecord[];
@@ -87,17 +86,11 @@ export const useChatScrollManager = ({
     const [isPinned, setIsPinned] = React.useState(true);
 
     const lastSessionIdRef = React.useRef<string | null>(null);
-    const currentSessionIdRef = React.useRef<string | null>(currentSessionId ?? null);
     const suppressUserScrollUntilRef = React.useRef<number>(0);
     const lastDirectScrollIntentAtRef = React.useRef<number>(0);
     const isPinnedRef = React.useRef(true);
     const lastScrollTopRef = React.useRef<number>(0);
 
-
-    React.useEffect(() => {
-        currentSessionIdRef.current = currentSessionId ?? null;
-    }, [currentSessionId]);
-
     const markProgrammaticScroll = React.useCallback(() => {
         suppressUserScrollUntilRef.current = Date.now() + PROGRAMMATIC_SCROLL_SUPPRESS_MS;
     }, []);
@@ -330,8 +323,8 @@ export const useChatScrollManager = ({
             }
         }
     }, [getDistanceFromBottom, getPinThreshold, scrollToBottomInternal, updateScrollButtonVisibility]);
- 
-     const getAnimationHandlers = React.useCallback((messageId: string): AnimationHandlers => {
+
+    const getAnimationHandlers = React.useCallback((messageId: string): AnimationHandlers => {
         const existing = animationHandlersRef.current.get(messageId);
         if (existing) {
             return existing;

packages/ui/src/lib/opencode/client.ts

@@ -478,56 +478,6 @@ class OpencodeService {
     return lowerMime === 'image/heic' || lowerMime === 'image/heif';
   }
 
-  /**
-   * Compress and resize image using Canvas.
-   */
-  private async compressImage(dataUrl: string, mimeType: string, quality = 0.8, maxWidth = 2048): Promise<string> {
-    if (typeof document === 'undefined') return dataUrl;
-
-    return new Promise((resolve) => {
-      const img = new Image();
-      img.onload = () => {
-        let width = img.width;
-        let height = img.height;
-
-        if (width > maxWidth || height > maxWidth) {
-          if (width > height) {
-            height = Math.round(height * (maxWidth / width));
-            width = maxWidth;
-          } else {
-            width = Math.round(width * (maxWidth / height));
-            height = maxWidth;
-          }
-        }
-
-        const canvas = document.createElement('canvas');
-        canvas.width = width;
-        canvas.height = height;
-        const ctx = canvas.getContext('2d');
-        if (!ctx) {
-          resolve(dataUrl);
-          return;
-        }
-
-        ctx.drawImage(img, 0, 0, width, height);
-
-        let targetMime = mimeType;
-        // Convert large PNGs to JPEG to save space
-        if (mimeType === 'image/png' && dataUrl.length > 2.5 * 1024 * 1024) {
-          targetMime = 'image/jpeg';
-        }
-
-        try {
-            resolve(canvas.toDataURL(targetMime, quality));
-        } catch {
-            resolve(dataUrl);
-        }
-      };
-      img.onerror = () => resolve(dataUrl);
-      img.src = dataUrl;
-    });
-  }
-
   /**
    * Convert HEIC image to JPEG.
    * Returns the original file if conversion fails.
@@ -592,23 +542,6 @@ class OpencodeService {
       return this.convertHeicToJpeg(file);
     }
 
-    // Handle large image compression (Resize > 2048px or > 1MB)
-    if (file.mime.startsWith('image/') && (file.mime === 'image/jpeg' || file.mime === 'image/png' || file.mime === 'image/webp')) {
-         // > ~1MB base64
-         if (file.url.length > 1.33 * 1024 * 1024) {
-             const compressedUrl = await this.compressImage(file.url, file.mime);
-             const newMime = compressedUrl.startsWith('data:image/jpeg') ? 'image/jpeg' : file.mime;
-             // Update the file object with compressed data
-             // We return a new object to avoid mutating the original file ref if used elsewhere, 
-             // but here we just return the part.
-             return {
-                 ...file,
-                 mime: newMime,
-                 url: compressedUrl
-             };
-         }
-    }
-
     // Handle text MIME normalization
     if (!this.shouldNormalizeToTextPlain(file.mime)) {
       return file;
@@ -647,6 +580,7 @@ class OpencodeService {
     agent?: string;
     variant?: string;
     files?: Array<{
+      id?: string;
       type: 'file';
       mime: string;
       filename?: string;
@@ -657,6 +591,7 @@ class OpencodeService {
       text: string;
       synthetic?: boolean;
       files?: Array<{
+        id?: string;
         type: 'file';
         mime: string;
         filename?: string;
@@ -696,6 +631,7 @@ class OpencodeService {
       for (const file of params.files) {
         const normalized = await this.normalizeFilePart(file);
         const filePart: FilePartInput = {
+          ...(file.id ? { id: file.id } : {}),
           type: 'file',
           mime: normalized.mime,
           filename: normalized.filename,
@@ -719,6 +655,7 @@ class OpencodeService {
           for (const file of additional.files) {
             const normalized = await this.normalizeFilePart(file);
             const filePart: FilePartInput = {
+              ...(file.id ? { id: file.id } : {}),
               type: 'file',
               mime: normalized.mime,
               filename: normalized.filename,

packages/ui/src/stores/fileStore.ts

@@ -1,6 +1,5 @@
 import { create } from "zustand";
 import { devtools, persist, createJSONStorage } from "zustand/middleware";
-import { opencodeClient } from "@/lib/opencode/client";
 import type { AttachedFile } from "./types/sessionTypes";
 import { getSafeStorage } from "./utils/safeStorage";
 
@@ -41,7 +40,7 @@ const guessMimeTypeFromName = (filename: string): string => {
         case "pdf":
             return "application/pdf";
         default:
-            return "text/plain";
+            return "application/octet-stream";
     }
 };
 
@@ -91,29 +90,30 @@ const guessMimeType = (file: File): string => {
     }
 };
 
-const base64ByteLength = (base64: string): number => {
-    const cleaned = base64.replace(/\s+/g, "");
-    if (!cleaned) {
-        return 0;
+const normalizeServerPath = (inputPath: string): string => inputPath.replace(/\\/g, "/").trim();
+
+const toFileUrl = (inputPath: string): string => {
+    const normalized = normalizeServerPath(inputPath);
+    if (normalized.startsWith("file://")) {
+        return normalized;
     }
-    const padding = cleaned.endsWith("==") ? 2 : cleaned.endsWith("=") ? 1 : 0;
-    return Math.floor((cleaned.length * 3) / 4) - padding;
+
+    const withLeadingSlash = normalized.startsWith("/") ? normalized : `/${normalized}`;
+    return `file://${encodeURI(withLeadingSlash)}`;
 };
 
-const base64EncodeBytes = (bytes: Uint8Array): string => {
-    const alphabet = "ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789+/";
-    let output = "";
-    for (let i = 0; i < bytes.length; i += 3) {
-        const a = bytes[i] ?? 0;
-        const b = bytes[i + 1];
-        const c = bytes[i + 2];
-        const triple = (a << 16) | ((b ?? 0) << 8) | (c ?? 0);
-        output += alphabet[(triple >> 18) & 63];
-        output += alphabet[(triple >> 12) & 63];
-        output += typeof b === "number" ? alphabet[(triple >> 6) & 63] : "=";
-        output += typeof c === "number" ? alphabet[triple & 63] : "=";
+const readRawFileAsDataUrl = async (absolutePath: string): Promise<string> => {
+    const response = await fetch(`/api/fs/raw?path=${encodeURIComponent(absolutePath)}`);
+    if (!response.ok) {
+        throw new Error(`Failed to read raw file: ${response.status}`);
     }
-    return output;
+    const blob = await response.blob();
+    return await new Promise<string>((resolve, reject) => {
+        const reader = new FileReader();
+        reader.onload = () => resolve(reader.result as string);
+        reader.onerror = reject;
+        reader.readAsDataURL(blob);
+    });
 };
 
 export const useFileStore = create<FileStore>()(
@@ -196,66 +196,33 @@ export const useFileStore = create<FileStore>()(
 
                 addServerFile: async (path: string, name: string, content?: string) => {
 
+                        const normalizedPath = normalizeServerPath(path);
                         const { attachedFiles } = get();
-                        const isDuplicate = attachedFiles.some((f) => f.serverPath === path && f.source === "server");
+                        const isDuplicate = attachedFiles.some((f) => normalizeServerPath(f.serverPath || "") === normalizedPath && f.source === "server");
                         if (isDuplicate) {
                             console.log(`Server file "${name}" is already attached`);
                             return;
                         }
 
-                        let fileContent = content;
-                        let encoding: "base64" | undefined;
-                        let resolvedMimeType: string | undefined;
-                        if (!fileContent) {
-                            try {
-
-                                const tempClient = opencodeClient.getApiClient();
-
-                                const lastSlashIndex = path.lastIndexOf("/");
-                                const directory = lastSlashIndex > 0 ? path.substring(0, lastSlashIndex) : "/";
-                                const filename = lastSlashIndex > 0 ? path.substring(lastSlashIndex + 1) : path;
-
-                                const response = await tempClient.file.read({
-                                    path: filename,
-                                    directory: directory,
-                                });
-
-                                if (response.data && "content" in response.data) {
-                                    fileContent = response.data.content;
-                                    encoding = response.data.encoding ?? undefined;
-                                    resolvedMimeType = response.data.mimeType ?? undefined;
-                                } else {
-                                    fileContent = "";
-                                }
-                            } catch (error) {
-                                console.error("Failed to read server file:", error);
-
-                                fileContent = `[File: ${name}]`;
-                            }
-                        }
-
-                        const inferredMime = resolvedMimeType || guessMimeTypeFromName(name);
+                        const inferredMime = guessMimeTypeFromName(name);
                         const safeMimeType = inferredMime && inferredMime.trim().length > 0 ? inferredMime : "application/octet-stream";
 
-                        const base64 = (() => {
-                            if (encoding === "base64") {
-                                return fileContent || "";
+                        const shouldInlineBinary = safeMimeType !== "text/plain" && safeMimeType !== "application/x-directory";
+
+                        let dataUrl = toFileUrl(normalizedPath);
+                        if (shouldInlineBinary) {
+                            try {
+                                dataUrl = await readRawFileAsDataUrl(normalizedPath);
+                            } catch (error) {
+                                console.warn("Failed to inline binary server file, falling back to file://", error);
                             }
-                            const encoder = new TextEncoder();
-                            const data = encoder.encode(fileContent || "");
-                            return base64EncodeBytes(data);
-                        })();
-
-                        const sizeBytes = encoding === "base64"
-                            ? base64ByteLength(base64)
-                            : new TextEncoder().encode(fileContent || "").length;
-
-                        if (sizeBytes > MAX_ATTACHMENT_SIZE) {
-                            throw new Error(`File "${name}" is too large. Maximum size is 50MB.`);
                         }
 
+                        const sizeBytes = typeof content === "string"
+                            ? new TextEncoder().encode(content).length
+                            : 0;
+
                         const file = new File([], name, { type: safeMimeType });
-                        const dataUrl = `data:${safeMimeType};base64,${base64}`;
 
                         const attachedFile: AttachedFile = {
                             id: `server-file-${Date.now()}-${Math.random().toString(36).substring(2, 9)}`,
@@ -265,7 +232,7 @@ export const useFileStore = create<FileStore>()(
                             filename: name,
                             size: sizeBytes,
                             source: "server",
-                            serverPath: path,
+                            serverPath: normalizedPath,
                         };
 
                         set((state) => ({
@@ -286,6 +253,12 @@ export const useFileStore = create<FileStore>()(
             {
                 name: "file-store",
                 storage: createJSONStorage(() => getSafeStorage()),
+                version: 3,
+                migrate: (persistedState) => {
+                    const state = persistedState as { attachedFiles?: AttachedFile[] } | undefined;
+                    return { attachedFiles: Array.isArray(state?.attachedFiles) ? state.attachedFiles : [] };
+                },
+                // Keep unsent draft attachments across restarts.
                 partialize: (state) => ({
                     attachedFiles: state.attachedFiles,
                 }),

packages/ui/src/stores/messageStore.ts

@@ -102,6 +102,15 @@ const computePartsTextLength = (parts: Part[] | undefined): number => {
     }, 0);
 };
 
+const toFileUrl = (inputPath: string): string => {
+    const normalized = inputPath.replace(/\\/g, "/").trim();
+    if (normalized.startsWith("file://")) {
+        return normalized;
+    }
+    const withLeadingSlash = normalized.startsWith("/") ? normalized : `/${normalized}`;
+    return `file://${encodeURI(withLeadingSlash)}`;
+};
+
 const hasFinishStop = (info: { finish?: string } | undefined): boolean => {
     return info?.finish === "stop";
 };
@@ -663,7 +672,12 @@ export const useMessageStore = create<MessageStore>()(
                                     type: "file" as const,
                                     mime: file.mimeType,
                                     filename: file.filename,
-                                    url: file.dataUrl,
+                                    url:
+                                        file.source === "server" &&
+                                        file.serverPath &&
+                                        (file.mimeType === "text/plain" || file.mimeType === "application/x-directory")
+                                            ? toFileUrl(file.serverPath)
+                                            : file.dataUrl,
                                 }));
 
                                 set((state) => {
@@ -687,7 +701,12 @@ export const useMessageStore = create<MessageStore>()(
                                         type: "file" as const,
                                         mime: file.mimeType,
                                         filename: file.filename,
-                                        url: file.dataUrl,
+                                        url:
+                                            file.source === "server" &&
+                                            file.serverPath &&
+                                            (file.mimeType === "text/plain" || file.mimeType === "application/x-directory")
+                                                ? toFileUrl(file.serverPath)
+                                                : file.dataUrl,
                                     })),
                                 }));
 

packages/ui/src/stores/utils/safeStorage.ts

@@ -56,29 +56,31 @@ const createSafeStorage = (): Storage => {
                 return;
             } catch {
                 disableStorage();
+                // Prevent stale previous value from surviving when writes fail (e.g. quota).
+                try {
+                    baseStorage.removeItem(key);
+                } catch {
+                    // noop
+                }
             }
         }
         fallback.setItem(key, value);
     };
 
     const safeRemove = (key: string) => {
-        if (storageAvailable) {
-            try {
-                baseStorage.removeItem(key);
-            } catch {
-                disableStorage();
-            }
+        try {
+            baseStorage.removeItem(key);
+        } catch {
+            disableStorage();
         }
         fallback.removeItem(key);
     };
 
     const safeClear = () => {
-        if (storageAvailable) {
-            try {
-                baseStorage.clear();
-            } catch {
-                disableStorage();
-            }
+        try {
+            baseStorage.clear();
+        } catch {
+            disableStorage();
         }
         fallback.clear();
     };
@@ -155,29 +157,31 @@ const createSafeSessionStorage = (): Storage => {
                 return;
             } catch {
                 disableStorage();
+                // Prevent stale previous value from surviving when writes fail (e.g. quota).
+                try {
+                    baseStorage.removeItem(key);
+                } catch {
+                    // noop
+                }
             }
         }
         fallback.setItem(key, value);
     };
 
     const safeRemove = (key: string) => {
-        if (storageAvailable) {
-            try {
-                baseStorage.removeItem(key);
-            } catch {
-                disableStorage();
-            }
+        try {
+            baseStorage.removeItem(key);
+        } catch {
+            disableStorage();
         }
         fallback.removeItem(key);
     };
 
     const safeClear = () => {
-        if (storageAvailable) {
-            try {
-                baseStorage.clear();
-            } catch {
-                disableStorage();
-            }
+        try {
+            baseStorage.clear();
+        } catch {
+            disableStorage();
         }
         fallback.clear();
     };

packages/vscode/src/bridge.ts

@@ -67,6 +67,12 @@ type ApiProxyRequestPayload = {
   bodyBase64?: string;
 };
 
+type ApiSessionMessageRequestPayload = {
+  path?: string;
+  headers?: Record<string, string>;
+  bodyText?: string;
+};
+
 type ApiProxyResponsePayload = {
   status: number;
   headers: Record<string, string>;
@@ -760,6 +766,23 @@ const collectHeaders = (headers: Headers): Record<string, string> => {
   return result;
 };
 
+const buildUnavailableApiResponse = (): ApiProxyResponsePayload => {
+  const body = JSON.stringify({ error: 'OpenCode API unavailable' });
+  return {
+    status: 503,
+    headers: { 'content-type': 'application/json' },
+    bodyBase64: base64EncodeUtf8(body),
+  };
+};
+
+const sanitizeForwardHeaders = (input: Record<string, string> | undefined): Record<string, string> => {
+  const headers: Record<string, string> = { ...(input || {}) };
+  delete headers['content-length'];
+  delete headers['host'];
+  delete headers['connection'];
+  return headers;
+};
+
 export async function handleBridgeMessage(message: BridgeRequest, ctx?: BridgeContext): Promise<BridgeResponse> {
   const { id, type, payload } = message;
 
@@ -768,12 +791,7 @@ export async function handleBridgeMessage(message: BridgeRequest, ctx?: BridgeCo
       case 'api:proxy': {
         const apiUrl = ctx?.manager?.getApiUrl();
         if (!apiUrl) {
-          const body = JSON.stringify({ error: 'OpenCode API unavailable' });
-          const data: ApiProxyResponsePayload = {
-            status: 503,
-            headers: { 'content-type': 'application/json' },
-            bodyBase64: base64EncodeUtf8(body),
-          };
+          const data = buildUnavailableApiResponse();
           return { id, type, success: true, data };
         }
 
@@ -788,7 +806,7 @@ export async function handleBridgeMessage(message: BridgeRequest, ctx?: BridgeCo
 
         const base = `${apiUrl.replace(/\/+$/, '')}/`;
         const targetUrl = new URL(normalizedPath.replace(/^\/+/, ''), base).toString();
-        const requestHeaders: Record<string, string> = { ...(headers || {}) };
+        const requestHeaders: Record<string, string> = sanitizeForwardHeaders(headers);
 
         // Ensure SSE requests are negotiated correctly.
         if (normalizedPath === '/event' || normalizedPath === '/global/event') {
@@ -830,6 +848,68 @@ export async function handleBridgeMessage(message: BridgeRequest, ctx?: BridgeCo
         }
       }
 
+      case 'api:session:message': {
+        const apiUrl = ctx?.manager?.getApiUrl();
+        if (!apiUrl) {
+          const data = buildUnavailableApiResponse();
+          return { id, type, success: true, data };
+        }
+
+        const { path: requestPath, headers, bodyText } = (payload || {}) as ApiSessionMessageRequestPayload;
+        const normalizedPath =
+          typeof requestPath === 'string' && requestPath.trim().length > 0
+            ? requestPath.trim().startsWith('/')
+              ? requestPath.trim()
+              : `/${requestPath.trim()}`
+            : '/';
+
+        if (!/^\/session\/[^/]+\/message(?:\?.*)?$/.test(normalizedPath)) {
+          const body = JSON.stringify({ error: 'Invalid session message proxy path' });
+          const data: ApiProxyResponsePayload = {
+            status: 400,
+            headers: { 'content-type': 'application/json' },
+            bodyBase64: base64EncodeUtf8(body),
+          };
+          return { id, type, success: true, data };
+        }
+
+        const base = `${apiUrl.replace(/\/+$/, '')}/`;
+        const targetUrl = new URL(normalizedPath.replace(/^\/+/, ''), base).toString();
+        const requestHeaders: Record<string, string> = sanitizeForwardHeaders(headers);
+
+        try {
+          const response = await fetch(targetUrl, {
+            method: 'POST',
+            headers: requestHeaders,
+            body: typeof bodyText === 'string' ? bodyText : '',
+            signal: AbortSignal.timeout(45000),
+          });
+
+          const arrayBuffer = await response.arrayBuffer();
+          const data: ApiProxyResponsePayload = {
+            status: response.status,
+            headers: collectHeaders(response.headers),
+            bodyBase64: Buffer.from(arrayBuffer).toString('base64'),
+          };
+
+          return { id, type, success: true, data };
+        } catch (error) {
+          const isTimeout =
+            error instanceof Error &&
+            ((error as Error & { name?: string }).name === 'TimeoutError' ||
+              (error as Error & { name?: string }).name === 'AbortError');
+          const body = JSON.stringify({
+            error: isTimeout ? 'OpenCode message forward timed out' : error instanceof Error ? error.message : 'OpenCode message forward failed',
+          });
+          const data: ApiProxyResponsePayload = {
+            status: isTimeout ? 504 : 503,
+            headers: { 'content-type': 'application/json' },
+            bodyBase64: base64EncodeUtf8(body),
+          };
+          return { id, type, success: true, data };
+        }
+      }
+
       case 'files:list': {
         const { path: dirPath } = payload as { path: string };
         const workspaceRoot = vscode.workspace.workspaceFolders?.[0]?.uri.fsPath || os.homedir();

packages/vscode/webview/api/bridge.ts

@@ -107,6 +107,15 @@ export async function proxyApiRequest(options: {
   return sendBridgeMessageWithOptions<ProxiedApiResponse>('api:proxy', options, { timeoutMs: 0 });
 }
 
+export async function proxySessionMessageRequest(options: {
+  path: string;
+  headers?: Record<string, string>;
+  bodyText: string;
+}): Promise<ProxiedApiResponse> {
+  // Keep parity with server-side direct forwarder: let extension host control timeout.
+  return sendBridgeMessageWithOptions<ProxiedApiResponse>('api:session:message', options, { timeoutMs: 0 });
+}
+
 export type ProxiedSseStartResponse = {
   status: number;
   headers: Record<string, string>;

packages/vscode/webview/main.tsx

@@ -1,5 +1,5 @@
 import { createVSCodeAPIs } from './api';
-import { onCommand, onThemeChange, proxyApiRequest, sendBridgeMessage, startSseProxy, stopSseProxy } from './api/bridge';
+import { onCommand, onThemeChange, proxyApiRequest, proxySessionMessageRequest, sendBridgeMessage, startSseProxy, stopSseProxy } from './api/bridge';
 import type { RuntimeAPIs } from '@openchamber/ui/lib/api/types';
 import {
   buildVSCodeThemeFromPalette,
@@ -343,7 +343,35 @@ const extractBodyBase64 = async (input: RequestInfo | URL, init: RequestInit | u
   return undefined;
 };
 
+const extractBodyText = async (input: RequestInfo | URL, init: RequestInit | undefined, method: string): Promise<string> => {
+  if (method === 'GET' || method === 'HEAD') return '';
+
+  if (input instanceof Request) {
+    const cloned = input.clone();
+    return await cloned.text();
+  }
+
+  const body = init?.body;
+  if (!body) return '';
+
+  if (typeof body === 'string') {
+    return body;
+  }
+
+  if (body instanceof URLSearchParams) {
+    return body.toString();
+  }
+
+  if (body instanceof Blob) {
+    return await body.text();
+  }
+
+  console.warn('[OpenChamber] Unsupported request body type for direct session proxy:', body);
+  return '';
+};
+
 const isSseApiPath = (pathname: string) => pathname === '/api/event' || pathname === '/api/global/event';
+const isSessionMessageApiPath = (pathname: string) => /^\/api\/session\/[^/]+\/message$/.test(pathname);
 
 const handleLocalApiRequest = async (url: URL, init?: RequestInit) => {
   const pathname = url.pathname;
@@ -761,6 +789,16 @@ window.fetch = async (input: RequestInfo | URL, init?: RequestInit) => {
       return new Response(stream, { status: start.status || 200, headers: start.headers || { 'content-type': 'text/event-stream' } });
     }
 
+    if (method === 'POST' && isSessionMessageApiPath(targetUrl.pathname)) {
+      const bodyText = await extractBodyText(input, init, method);
+      const proxied = await proxySessionMessageRequest({ path: suffixPath, headers, bodyText });
+      const body = proxied.bodyBase64 ? decodeBase64(proxied.bodyBase64) : new Uint8Array();
+      const response = new Response(body, { status: proxied.status, headers: proxied.headers });
+      recordBootstrapFetch(targetUrl.pathname, response.ok);
+      maybeHideLoadingOverlay();
+      return response;
+    }
+
     const bodyBase64 = await extractBodyBase64(input, init, method);
     const proxied = await proxyApiRequest({ method, path: suffixPath, headers, bodyBase64 });
     const body = proxied.bodyBase64 ? decodeBase64(proxied.bodyBase64) : new Uint8Array();

packages/web/server/index.js

@@ -1,5 +1,4 @@
 import express from 'express';
-import { createProxyMiddleware } from 'http-proxy-middleware';
 import path from 'path';
 import { spawn, spawnSync } from 'child_process';
 import fs from 'fs';
@@ -4630,6 +4629,157 @@ function setupProxy(app) {
     next();
   });
 
+  const isSseApiPath = (path) => path === '/event' || path === '/global/event';
+
+  const forwardSseRequest = async (req, res) => {
+    const startedAt = Date.now();
+    const upstreamPath = req.originalUrl.replace(/^\/api/, '');
+    const targetUrl = buildOpenCodeUrl(upstreamPath, '');
+    const authHeaders = getOpenCodeAuthHeaders();
+
+    const requestHeaders = {
+      ...(typeof req.headers.accept === 'string' ? { accept: req.headers.accept } : { accept: 'text/event-stream' }),
+      'cache-control': 'no-cache',
+      connection: 'keep-alive',
+      ...(authHeaders.Authorization ? { Authorization: authHeaders.Authorization } : {}),
+    };
+
+    const controller = new AbortController();
+    let connectTimer = null;
+    let idleTimer = null;
+    let heartbeatTimer = null;
+    let endedBy = 'upstream-end';
+
+    const cleanup = () => {
+      if (connectTimer) {
+        clearTimeout(connectTimer);
+        connectTimer = null;
+      }
+      if (idleTimer) {
+        clearTimeout(idleTimer);
+        idleTimer = null;
+      }
+      if (heartbeatTimer) {
+        clearInterval(heartbeatTimer);
+        heartbeatTimer = null;
+      }
+      req.off('close', onClientClose);
+    };
+
+    const resetIdleTimeout = () => {
+      if (idleTimer) {
+        clearTimeout(idleTimer);
+      }
+      idleTimer = setTimeout(() => {
+        endedBy = 'idle-timeout';
+        controller.abort();
+      }, 5 * 60 * 1000);
+    };
+
+    const onClientClose = () => {
+      endedBy = 'client-disconnect';
+      controller.abort();
+    };
+
+    req.on('close', onClientClose);
+
+    try {
+      connectTimer = setTimeout(() => {
+        endedBy = 'connect-timeout';
+        controller.abort();
+      }, 10 * 1000);
+
+      const upstreamResponse = await fetch(targetUrl, {
+        method: 'GET',
+        headers: requestHeaders,
+        signal: controller.signal,
+      });
+
+      if (connectTimer) {
+        clearTimeout(connectTimer);
+        connectTimer = null;
+      }
+
+      if (!upstreamResponse.ok || !upstreamResponse.body) {
+        const body = await upstreamResponse.text().catch(() => '');
+        cleanup();
+        if (!res.headersSent) {
+          if (upstreamResponse.headers.has('content-type')) {
+            res.setHeader('content-type', upstreamResponse.headers.get('content-type'));
+          }
+          res.status(upstreamResponse.status).send(body);
+        }
+        return;
+      }
+
+      const upstreamContentType = upstreamResponse.headers.get('content-type') || 'text/event-stream';
+      res.status(upstreamResponse.status);
+      res.setHeader('content-type', upstreamContentType);
+      res.setHeader('cache-control', 'no-cache');
+      res.setHeader('connection', 'keep-alive');
+      res.setHeader('x-accel-buffering', 'no');
+      res.setHeader('x-content-type-options', 'nosniff');
+      if (typeof res.flushHeaders === 'function') {
+        res.flushHeaders();
+      }
+
+      resetIdleTimeout();
+      heartbeatTimer = setInterval(() => {
+        if (res.writableEnded || controller.signal.aborted) {
+          return;
+        }
+        try {
+          res.write(': ping\n\n');
+          resetIdleTimeout();
+        } catch {
+        }
+      }, 30 * 1000);
+
+      const reader = upstreamResponse.body.getReader();
+      try {
+        while (true) {
+          const { done, value } = await reader.read();
+          if (done) {
+            endedBy = endedBy === 'upstream-end' ? 'upstream-finished' : endedBy;
+            break;
+          }
+          if (controller.signal.aborted) {
+            break;
+          }
+          if (value && value.length > 0) {
+            res.write(Buffer.from(value));
+            resetIdleTimeout();
+          }
+        }
+      } finally {
+        try {
+          reader.releaseLock();
+        } catch {
+        }
+      }
+
+      cleanup();
+      if (!res.writableEnded) {
+        res.end();
+      }
+      console.log(`SSE forward ${upstreamPath} closed (${endedBy}) in ${Date.now() - startedAt}ms`);
+    } catch (error) {
+      cleanup();
+      const isTimeout = error?.name === 'TimeoutError' || error?.name === 'AbortError';
+      if (!res.headersSent) {
+        res.status(isTimeout ? 504 : 503).json({
+          error: isTimeout ? 'OpenCode SSE forward timed out' : 'OpenCode SSE forward failed',
+        });
+      } else if (!res.writableEnded) {
+        res.end();
+      }
+      console.warn(`SSE forward ${upstreamPath} failed (${endedBy}):`, error?.message || error);
+    }
+  };
+
+  app.get('/api/event', forwardSseRequest);
+  app.get('/api/global/event', forwardSseRequest);
+
   app.use('/api', (_req, _res, next) => {
     ensureOpenCodeApiPrefix();
     next();
@@ -4651,66 +4801,162 @@ function setupProxy(app) {
   });
 
 
-  const proxyMiddleware = createProxyMiddleware({
-    target: openCodePort ? `http://localhost:${openCodePort}` : 'http://127.0.0.1:0',
-    router: () => {
-      if (!openCodePort) {
-        return 'http://127.0.0.1:0';
-      }
-      return `http://localhost:${openCodePort}`;
-    },
-    changeOrigin: true,
-    pathRewrite: (path) => {
-      if (!path.startsWith('/api')) {
-        return path;
+  const hopByHopRequestHeaders = new Set([
+    'host',
+    'connection',
+    'content-length',
+    'transfer-encoding',
+    'keep-alive',
+    'te',
+    'trailer',
+    'upgrade',
+  ]);
+
+  const hopByHopResponseHeaders = new Set([
+    'connection',
+    'content-length',
+    'transfer-encoding',
+    'keep-alive',
+    'te',
+    'trailer',
+    'upgrade',
+    'www-authenticate',
+  ]);
+
+  const collectForwardHeaders = (req) => {
+    const authHeaders = getOpenCodeAuthHeaders();
+    const headers = {};
+
+    for (const [key, value] of Object.entries(req.headers || {})) {
+      if (!value) continue;
+      const lowerKey = key.toLowerCase();
+      if (hopByHopRequestHeaders.has(lowerKey)) continue;
+      headers[lowerKey] = Array.isArray(value) ? value.join(', ') : String(value);
+    }
+
+    if (authHeaders.Authorization) {
+      headers.Authorization = authHeaders.Authorization;
+    }
+
+    return headers;
+  };
+
+  const collectRequestBodyBuffer = async (req) => {
+    if (Buffer.isBuffer(req.body)) {
+      return req.body;
+    }
+
+    if (typeof req.body === 'string') {
+      return Buffer.from(req.body);
+    }
+
+    if (req.body && typeof req.body === 'object') {
+      return Buffer.from(JSON.stringify(req.body));
+    }
+
+    if (req.readableEnded) {
+      return Buffer.alloc(0);
+    }
+
+    return await new Promise((resolve, reject) => {
+      const chunks = [];
+      req.on('data', (chunk) => {
+        chunks.push(Buffer.isBuffer(chunk) ? chunk : Buffer.from(chunk));
+      });
+      req.on('end', () => resolve(Buffer.concat(chunks)));
+      req.on('error', reject);
+    });
+  };
+
+  const forwardGenericApiRequest = async (req, res) => {
+    try {
+      const upstreamPath = req.originalUrl.replace(/^\/api/, '');
+      const targetUrl = buildOpenCodeUrl(upstreamPath, '');
+      const headers = collectForwardHeaders(req);
+      const method = String(req.method || 'GET').toUpperCase();
+      const hasBody = method !== 'GET' && method !== 'HEAD';
+      const bodyBuffer = hasBody ? await collectRequestBodyBuffer(req) : null;
+
+      const upstreamResponse = await fetch(targetUrl, {
+        method,
+        headers,
+        body: hasBody ? bodyBuffer : undefined,
+        signal: AbortSignal.timeout(LONG_REQUEST_TIMEOUT_MS),
+      });
+
+      for (const [key, value] of upstreamResponse.headers.entries()) {
+        const lowerKey = key.toLowerCase();
+        if (hopByHopResponseHeaders.has(lowerKey)) {
+          continue;
+        }
+        res.setHeader(key, value);
       }
 
-      const suffix = path.slice(4) || '/';
+      const upstreamBody = Buffer.from(await upstreamResponse.arrayBuffer());
+      res.status(upstreamResponse.status).send(upstreamBody);
+    } catch (error) {
+      if (!res.headersSent) {
+        const isTimeout = error?.name === 'TimeoutError' || error?.name === 'AbortError';
+        res.status(isTimeout ? 504 : 503).json({
+          error: isTimeout ? 'OpenCode request timed out' : 'OpenCode service unavailable',
+        });
+      }
+    }
+  };
 
-      return suffix;
-    },
-    ws: false,
-    // v3.x API: callbacks go in 'on' object
-    on: {
-      error: (err, req, res) => {
-        console.error(`Proxy error: ${err.message}`);
-        if (!res.headersSent) {
-          res.status(503).json({ error: 'OpenCode service unavailable' });
-        }
-      },
-      proxyReq: (proxyReq, req, res) => {
-        console.log(`Proxying ${req.method} ${req.path} to OpenCode`);
-        const authHeaders = getOpenCodeAuthHeaders();
-        if (authHeaders.Authorization) {
-          proxyReq.setHeader('Authorization', authHeaders.Authorization);
-        }
+  // Dedicated forwarder for large session message payloads.
+  // This avoids edge-cases in generic proxy streaming for multi-file attachments.
+  app.post('/api/session/:sessionId/message', express.raw({ type: '*/*', limit: '50mb' }), async (req, res) => {
+    try {
+      const upstreamPath = req.originalUrl.replace(/^\/api/, '');
+      const targetUrl = buildOpenCodeUrl(upstreamPath, '');
+      const authHeaders = getOpenCodeAuthHeaders();
 
-        if (req.headers.accept && req.headers.accept.includes('text/event-stream')) {
-          proxyReq.setHeader('Accept', 'text/event-stream');
-          proxyReq.setHeader('Cache-Control', 'no-cache');
-          proxyReq.setHeader('Connection', 'keep-alive');
-        }
-      },
-      proxyRes: (proxyRes, req, res) => {
-        // Strip WWW-Authenticate to prevent browser's native Basic Auth popup
-        if (proxyRes.headers['www-authenticate']) {
-          delete proxyRes.headers['www-authenticate'];
-        }
+      const headers = {
+        ...(typeof req.headers['content-type'] === 'string' ? { 'content-type': req.headers['content-type'] } : { 'content-type': 'application/json' }),
+        ...(typeof req.headers.accept === 'string' ? { accept: req.headers.accept } : {}),
+        ...(authHeaders.Authorization ? { Authorization: authHeaders.Authorization } : {}),
+      };
 
-        if (req.url?.includes('/event')) {
-          proxyRes.headers['Access-Control-Allow-Origin'] = '*';
-          proxyRes.headers['Access-Control-Allow-Headers'] = 'Cache-Control, Accept';
-          proxyRes.headers['Content-Type'] = 'text/event-stream';
-          proxyRes.headers['Cache-Control'] = 'no-cache';
-          proxyRes.headers['Connection'] = 'keep-alive';
-          proxyRes.headers['X-Accel-Buffering'] = 'no';
-          proxyRes.headers['X-Content-Type-Options'] = 'nosniff';
-        }
+      const bodyBuffer = Buffer.isBuffer(req.body)
+        ? req.body
+        : Buffer.from(typeof req.body === 'string' ? req.body : '');
+
+      const upstreamResponse = await fetch(targetUrl, {
+        method: 'POST',
+        headers,
+        body: bodyBuffer,
+        signal: AbortSignal.timeout(45000),
+      });
+
+      const upstreamBody = Buffer.from(await upstreamResponse.arrayBuffer());
+
+      if (upstreamResponse.headers.has('content-type')) {
+        res.setHeader('content-type', upstreamResponse.headers.get('content-type'));
+      }
+
+      res.status(upstreamResponse.status).send(upstreamBody);
+    } catch (error) {
+      if (!res.headersSent) {
+        const isTimeout = error?.name === 'TimeoutError' || error?.name === 'AbortError';
+        res.status(isTimeout ? 504 : 503).json({
+          error: isTimeout ? 'OpenCode message forward timed out' : 'OpenCode message forward failed',
+        });
       }
     }
   });
 
-  app.use('/api', proxyMiddleware);
+  app.use('/api', (req, res, next) => {
+    if (isSseApiPath(req.path)) {
+      return next();
+    }
+
+    if (req.method === 'POST' && /\/session\/[^/]+\/message$/.test(req.path || '')) {
+      return next();
+    }
+
+    return forwardGenericApiRequest(req, res);
+  });
 }
 
 function startHealthMonitoring() {
@@ -8478,7 +8724,36 @@ async function main(options = {}) {
         })
         .join('\n\n');
 
-      const prompt = `You are drafting git commit notes for this codebase. Respond in JSON of the shape {"subject": string, "highlights": string[]} (ONLY the JSON in response, no markdown wrappers or anything except JSON) with these rules:\n- subject follows our convention: type[optional-scope]: summary (examples: "feat: add diff virtualization", "fix(chat): restore enter key handling")\n- allowed types: feat, fix, chore, style, refactor, perf, docs, test, build, ci (choose the best match or fallback to chore)\n- summary must be imperative, concise, <= 70 characters, no trailing punctuation\n- scope is optional; include only when obvious from filenames/folders; do not invent scopes\n- focus on the most impactful user-facing change; if multiple capabilities ship together, align the subject with the dominant theme and use highlights to cover the other major outcomes\n- highlights array should contain 2-3 plain sentences (<= 90 chars each) that describe distinct features or UI changes users will notice (e.g. "Add per-file revert action in Changes list"). Avoid subjective benefit statements, marketing tone, repeating the subject, or referencing helper function names. Highlight additions such as new controls/buttons, new actions (e.g. revert), or stored state changes explicitly. Skip highlights if fewer than two meaningful points exist.\n- text must be plain (no markdown bullets); each highlight should start with an uppercase verb\n\nDiff summary:\n${diffSummaries}`;
+      const prompt = `You are generating a Conventional Commits subject line from the provided diff.
+
+Return EXACTLY one JSON object (no code fences, no extra keys, no extra text):
+{"subject": string, "highlights": string[]}
+
+Non-negotiable:
+- Output must be valid JSON (double quotes).
+- Only claim what is supported by the diff. If unsure, be more general; do not guess.
+
+subject:
+- Format: <type>: <summary> (NO scope; never write type(scope))
+- Allowed types: feat, fix, refactor, perf, docs, test, build, ci, chore, style, revert
+- Choose type (prefer fix when ambiguous):
+  - fix: any bug/regression/wrong behavior (state, selection, navigation, persistence, crash)
+  - feat: new user-facing capability or new workflow (not just guardrails/defaults)
+  - refactor/perf/docs/test/build/ci/style/chore/revert: only when clearly the primary change
+- Summary style:
+  - imperative, present tense, outcome-first
+  - <= 72 characters, no trailing period
+  - avoid filenames, internal function names, and implementation details
+
+highlights:
+- 0-3 items; it is OK to return [].
+- Each item: one plain sentence, <= 90 chars, starts with an Uppercase verb.
+- Must add information not already in the subject.
+- Prefer user-observable behaviors (UI flow, navigation, selection, default view, persistence).
+- No markdown bullets, no file paths, no helper names.
+
+Diff summary (may be truncated):
+${diffSummaries}`;
 
       const model = 'gpt-5-nano';