diff --git a/src/app/api/chat/route.ts b/src/app/api/chat/route.ts
index b6c3ccf4..531db3fd 100644
--- a/src/app/api/chat/route.ts
+++ b/src/app/api/chat/route.ts
@@ -294,6 +294,13 @@ async function handlePOST(req: Request) {
     // Prepare provider options
     // The Gateway passes these through to the specific provider
     const isClaudeModel = modelId.includes("claude");
+    const vertexProject = process.env.GOOGLE_VERTEX_PROJECT;
+    const vertexLocation = process.env.GOOGLE_VERTEX_LOCATION || "us-central1";
+    const vertexClientEmail = process.env.GOOGLE_CLIENT_EMAIL;
+    const vertexPrivateKey = process.env.GOOGLE_PRIVATE_KEY?.replace(/\\n/g, "\n");
+    const hasVertexByok =
+      vertexProject && vertexClientEmail && vertexPrivateKey;
+
     let providerOptions: any = {
       gateway: {
         // Route Claude models through Vertex AI only
@@ -302,6 +309,22 @@ async function handlePOST(req: Request) {
         models: ["google/gemini-2.5-flash"],
         // Track usage per end-user for analytics
         ...(userId ? { user: userId } : {}),
+        // BYOK for Vertex: use GCP credentials so Claude (Haiku, etc.) bypasses Vercel balance
+        ...(isClaudeModel &&
+        hasVertexByok && {
+          byok: {
+            vertex: [
+              {
+                project: vertexProject!,
+                location: vertexLocation,
+                googleCredentials: {
+                  clientEmail: vertexClientEmail!,
+                  privateKey: vertexPrivateKey!,
+                },
+              },
+            ],
+          },
+        }),
         // Fail fast if provider doesn't start streaming within 30s (BYOK only)
         providerTimeouts: {
           byok: {
diff --git a/src/app/api/upload-file/route.ts b/src/app/api/upload-file/route.ts
index 6d48fbf2..06c11b96 100644
--- a/src/app/api/upload-file/route.ts
+++ b/src/app/api/upload-file/route.ts
@@ -5,6 +5,10 @@ import { NextRequest, NextResponse } from 'next/server';
 import { writeFile, mkdir } from 'fs/promises';
 import { join } from 'path';
 import { existsSync } from 'fs';
+import {
+  isOfficeDocument,
+  getOfficeDocumentConvertUrl,
+} from "@/lib/uploads/office-document-validation";
 
 export const maxDuration = 30;
 
@@ -61,8 +65,17 @@ export async function POST(request: NextRequest) {
       );
     }
 
-    // Accept all file types (removed image-only restriction)
-    // File type validation can be done client-side if needed
+    // Reject Office documents — convert to PDF at ilovepdf.com
+    const convertUrl = getOfficeDocumentConvertUrl(file);
+    if (convertUrl) {
+      return NextResponse.json(
+        {
+          error: "Word, Excel, and PowerPoint files are not supported. Convert to PDF first.",
+          convertUrl,
+        },
+        { status: 400 }
+      );
+    }
 
     // Validate file size (50MB limit)
     const maxSize = 50 * 1024 * 1024; // 50MB
diff --git a/src/app/api/upload-url/route.ts b/src/app/api/upload-url/route.ts
index 79edcb96..eb186f84 100644
--- a/src/app/api/upload-url/route.ts
+++ b/src/app/api/upload-url/route.ts
@@ -3,6 +3,7 @@ import { auth } from "@/lib/auth";
 import { createClient } from '@supabase/supabase-js';
 import { NextRequest, NextResponse } from 'next/server';
 import { withApiLogging } from "@/lib/with-api-logging";
+import { getOfficeDocumentConvertUrlFromMeta } from "@/lib/uploads/office-document-validation";
 
 export const maxDuration = 10;
 
@@ -28,7 +29,7 @@ async function handlePOST(request: NextRequest) {
     }
 
     const body = await request.json();
-    const { filename, contentType } = body;
+    const { filename, contentType = "" } = body;
 
     if (!filename || typeof filename !== 'string') {
       return NextResponse.json(
@@ -37,6 +38,18 @@ async function handlePOST(request: NextRequest) {
       );
     }
 
+    // Reject Office documents — convert to PDF at ilovepdf.com
+    const convertUrl = getOfficeDocumentConvertUrlFromMeta(filename, contentType);
+    if (convertUrl) {
+      return NextResponse.json(
+        {
+          error: "Word, Excel, and PowerPoint files are not supported. Convert to PDF first.",
+          convertUrl,
+        },
+        { status: 400 }
+      );
+    }
+
     const storageType = process.env.STORAGE_TYPE || 'supabase';
 
     if (storageType === 'local') {
diff --git a/src/app/api/workspaces/[id]/events/route.ts b/src/app/api/workspaces/[id]/events/route.ts
index 27ef8c3e..3f1f9f05 100644
--- a/src/app/api/workspaces/[id]/events/route.ts
+++ b/src/app/api/workspaces/[id]/events/route.ts
@@ -1,6 +1,40 @@
 import { NextRequest, NextResponse } from "next/server";
 import type { WorkspaceEvent, EventResponse } from "@/lib/workspace/events";
 import { checkAndCreateSnapshot } from "@/lib/workspace/snapshot-manager";
+
+/** Strip ocrPages/textContent from PDF items — client doesn't need them for display. */
+function stripPdfOcrFromItem(item: { type?: string; data?: unknown }): void {
+  if (item?.type === "pdf" && item.data && typeof item.data === "object") {
+    const d = item.data as Record<string, unknown>;
+    delete d.ocrPages;
+    delete d.textContent;
+  }
+}
+
+function stripPdfOcrFromState(state: { items?: Array<{ type?: string; data?: unknown }> } | undefined): void {
+  state?.items?.forEach(stripPdfOcrFromItem);
+}
+
+function stripPdfOcrFromEventPayload(event: WorkspaceEvent): void {
+  const p = event.payload as Record<string, unknown>;
+  if (event.type === "ITEM_CREATED" && p?.item) stripPdfOcrFromItem(p.item as { type?: string; data?: unknown });
+  if (event.type === "ITEM_UPDATED") {
+    const changes = p?.changes as Record<string, unknown> | undefined;
+    if (changes?.data && typeof changes.data === "object") {
+      const d = changes.data as Record<string, unknown>;
+      delete d.ocrPages;
+      delete d.textContent;
+    }
+  }
+  if (event.type === "BULK_ITEMS_UPDATED") {
+    (p?.addedItems as Array<{ type?: string; data?: unknown }> | undefined)?.forEach(stripPdfOcrFromItem);
+    (p?.items as Array<{ type?: string; data?: unknown }> | undefined)?.forEach(stripPdfOcrFromItem);
+  }
+  if (event.type === "WORKSPACE_SNAPSHOT" && p?.items) {
+    (p.items as Array<{ type?: string; data?: unknown }>).forEach(stripPdfOcrFromItem);
+  }
+}
+
 import { loadWorkspaceState } from "@/lib/workspace/state-loader";
 import { hasDuplicateName } from "@/lib/workspace/unique-name";
 import { db, workspaceEvents } from "@/lib/db/client";
@@ -177,6 +211,10 @@ async function handleGET(
     ? Math.max(...eventsData.map(e => e.version))
     : (snapshotVersion || 0);
 
+  // Strip ocrPages/textContent from PDF items — client doesn't need them for display
+  if (latestSnapshot?.state) stripPdfOcrFromState(latestSnapshot.state as { items?: Array<{ type?: string; data?: unknown }> });
+  events.forEach(stripPdfOcrFromEventPayload);
+
   const response: EventResponse = {
     events,
     version: maxVersion,
@@ -324,6 +362,7 @@ async function handlePOST(
       userName: e.userName || undefined,
       id: e.eventId,
     } as WorkspaceEvent));
+    events.forEach(stripPdfOcrFromEventPayload);
 
     const totalTime = Date.now() - startTime;
     timings.total = totalTime;
diff --git a/src/app/dashboard/page.tsx b/src/app/dashboard/page.tsx
index 999475e5..4746e99f 100644
--- a/src/app/dashboard/page.tsx
+++ b/src/app/dashboard/page.tsx
@@ -28,6 +28,7 @@ import { DashboardLayout } from "@/components/layout/DashboardLayout";
 import { SplitViewLayout } from "@/components/layout/SplitViewLayout";
 import { ItemPanelContent } from "@/components/workspace-canvas/ItemPanelContent";
 import WorkspaceHeader from "@/components/workspace-canvas/WorkspaceHeader";
+import { WorkspaceSearchDialog } from "@/components/workspace-canvas/WorkspaceSearchDialog";
 import { SidebarProvider, useSidebar } from "@/components/ui/sidebar";
 import { MobileWarning } from "@/components/ui/MobileWarning";
 import { AnonymousSessionHandler, SidebarCoordinator } from "@/components/layout/SessionHandler";
@@ -216,13 +217,11 @@ function DashboardContent({
   const isDesktop = useMediaQuery("(min-width: 768px)");
   const showJsonView = useUIStore((state) => state.showJsonView);
   const isChatExpanded = useUIStore((state) => state.isChatExpanded);
-  const searchQuery = useUIStore((state) => state.searchQuery);
   const isChatMaximized = useUIStore((state) => state.isChatMaximized);
   const workspacePanelSize = useUIStore((state) => state.workspacePanelSize);
   const showCreateWorkspaceModal = useUIStore((state) => state.showCreateWorkspaceModal);
   const setShowJsonView = useUIStore((state) => state.setShowJsonView);
   const setIsChatExpanded = useUIStore((state) => state.setIsChatExpanded);
-  const setSearchQuery = useUIStore((state) => state.setSearchQuery);
   const setIsChatMaximized = useUIStore((state) => state.setIsChatMaximized);
   const setOpenModalItemId = useUIStore((state) => state.setOpenModalItemId);
   const setShowCreateWorkspaceModal = useUIStore((state) => state.setShowCreateWorkspaceModal);
@@ -265,6 +264,9 @@ function DashboardContent({
     isDesktop,
   });
 
+  // Search dialog state for Cmd+K command palette
+  const [searchDialogOpen, setSearchDialogOpen] = useState(false);
+
   // Keyboard shortcuts
   useKeyboardShortcuts(
     toggleChatExpanded,
@@ -272,7 +274,9 @@ function DashboardContent({
       onToggleSidebar: toggleSidebar,
       onToggleChatMaximize: toggleChatMaximized,
       onFocusSearch: () => {
-        titleInputRef.current?.focus();
+        if (currentWorkspaceId && !isLoadingWorkspace) {
+          setSearchDialogOpen(true);
+        }
       },
     }
   );
@@ -455,8 +459,7 @@ function DashboardContent({
             currentSlug={currentSlug}
             state={state}
             showJsonView={showJsonView}
-            searchQuery={searchQuery}
-            onSearchChange={setSearchQuery}
+            onOpenSearch={() => setSearchDialogOpen(true)}
             isSaving={isSaving}
             lastSavedAt={lastSavedAt}
             hasUnsavedChanges={hasUnsavedChanges}
@@ -494,7 +497,7 @@ function DashboardContent({
         onFlushPendingChanges={operations.flushPendingChanges}
       />
     );
-  }, [viewMode, state.items, loadingCurrentWorkspace, isLoadingWorkspace, currentWorkspaceId, currentSlug, state, showJsonView, searchQuery, isSaving, lastSavedAt, hasUnsavedChanges, isChatMaximized, isDesktop, isChatExpanded, currentWorkspaceTitle, currentWorkspaceIcon, currentWorkspaceColor, operations, manualSave, setSearchQuery, setIsChatExpanded, setOpenModalItemId, handleShowHistory, titleInputRef, scrollAreaRef, getStatePreviewJSON]);
+  }, [viewMode, state.items, loadingCurrentWorkspace, isLoadingWorkspace, currentWorkspaceId, currentSlug, state, showJsonView, isSaving, lastSavedAt, hasUnsavedChanges, isChatMaximized, isDesktop, isChatExpanded, currentWorkspaceTitle, currentWorkspaceIcon, currentWorkspaceColor, operations, manualSave, setSearchDialogOpen, setIsChatExpanded, setOpenModalItemId, handleShowHistory, titleInputRef, scrollAreaRef, getStatePreviewJSON]);
 
   // Build the single panel content (for workspace+panel mode)
   const panelContent = useMemo(() => {
@@ -553,8 +556,7 @@ function DashboardContent({
           !showJsonView && !isChatMaximized && currentWorkspaceId && !isLoadingWorkspace ? (
             <WorkspaceHeader
               titleInputRef={titleInputRef as React.RefObject<HTMLInputElement>}
-              searchQuery={searchQuery}
-              onSearchChange={setSearchQuery}
+              onOpenSearch={() => setSearchDialogOpen(true)}
               currentWorkspaceId={currentWorkspaceId}
               isSaving={isSaving}
               lastSavedAt={lastSavedAt}
@@ -626,8 +628,7 @@ function DashboardContent({
             currentSlug={currentSlug}
             state={state}
             showJsonView={showJsonView}
-            searchQuery={searchQuery}
-            onSearchChange={setSearchQuery}
+            onOpenSearch={() => setSearchDialogOpen(true)}
             isSaving={isSaving}
             lastSavedAt={lastSavedAt}
             hasUnsavedChanges={hasUnsavedChanges}
@@ -695,6 +696,13 @@ function DashboardContent({
         onRevertToVersion={revertToVersion}
         items={currentWorkspace?.state?.items || []}
       />
+      <WorkspaceSearchDialog
+        open={searchDialogOpen}
+        onOpenChange={setSearchDialogOpen}
+        items={state.items ?? []}
+        currentWorkspaceId={currentWorkspaceId}
+        isLoadingWorkspace={isLoadingWorkspace}
+      />
     </PdfEngineWrapper>
   );
 }
@@ -745,12 +753,6 @@ function DashboardView() {
     lastTrackedWorkspaceIdRef.current = currentWorkspaceId;
   }, [currentWorkspaceId, markWorkspaceOpened]);
 
-  // Reset search query when workspace changes
-  const setSearchQuery = useUIStore((state) => state.setSearchQuery);
-  useEffect(() => {
-    setSearchQuery('');
-  }, [currentWorkspaceId, setSearchQuery]);
-
   // Sync active folder with URL query param (?folder=<id>)
   // Reset folder/panels when workspace changes
   // and enables browser-native back/forward for folder navigation
diff --git a/src/components/assistant-ui/AIFeedbackDialog.tsx b/src/components/assistant-ui/AIFeedbackDialog.tsx
new file mode 100644
index 00000000..24532bac
--- /dev/null
+++ b/src/components/assistant-ui/AIFeedbackDialog.tsx
@@ -0,0 +1,97 @@
+"use client";
+
+import { useState, useCallback } from "react";
+import {
+  Dialog,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from "@/components/ui/dialog";
+import { Button } from "@/components/ui/button";
+import { Textarea } from "@/components/ui/textarea";
+import { usePostHog } from "posthog-js/react";
+import { toast } from "sonner";
+import { useAuiState } from "@assistant-ui/react";
+import { useWorkspaceStore } from "@/lib/stores/workspace-store";
+
+interface AIFeedbackDialogProps {
+  open: boolean;
+  onOpenChange: (open: boolean) => void;
+}
+
+export function AIFeedbackDialog({ open, onOpenChange }: AIFeedbackDialogProps) {
+  const [feedback, setFeedback] = useState("");
+  const [isSubmitting, setIsSubmitting] = useState(false);
+  const posthog = usePostHog();
+
+  const threadListItemId = useAuiState(({ threadListItem }) => (threadListItem as { id?: string })?.id);
+  const mainThreadId = useAuiState(({ threads }) => (threads as { mainThreadId?: string })?.mainThreadId);
+  const threadId = threadListItemId ?? mainThreadId;
+  const workspaceId = useWorkspaceStore((s) => s.currentWorkspaceId);
+
+  const handleSubmit = useCallback(() => {
+    setIsSubmitting(true);
+
+    if (posthog) {
+      posthog.capture("ai-feedback-reported", {
+        feedback: feedback.trim(),
+        thread_id: threadId ?? undefined,
+        workspace_id: workspaceId ?? undefined,
+        source: "composer",
+      });
+    }
+
+    toast.success("Feedback submitted—thank you!");
+    setFeedback("");
+    onOpenChange(false);
+    setIsSubmitting(false);
+  }, [feedback, threadId, workspaceId, posthog, onOpenChange]);
+
+  const handleOpenChange = useCallback(
+    (nextOpen: boolean) => {
+      if (!nextOpen && !isSubmitting) {
+        setFeedback("");
+      }
+      onOpenChange(nextOpen);
+    },
+    [onOpenChange, isSubmitting]
+  );
+
+  return (
+    <Dialog open={open} onOpenChange={handleOpenChange}>
+      <DialogContent className="sm:max-w-md">
+        <DialogHeader>
+          <DialogTitle>Report AI Issue</DialogTitle>
+          <DialogDescription>
+            What went wrong with the AI? Your feedback helps us improve.
+          </DialogDescription>
+        </DialogHeader>
+
+        <div className="space-y-4">
+          <Textarea
+            placeholder="Describe what went wrong (optional)..."
+            value={feedback}
+            onChange={(e) => setFeedback(e.target.value)}
+            rows={4}
+            className="resize-none"
+          />
+        </div>
+
+        <DialogFooter>
+          <Button
+            variant="outline"
+            onClick={() => handleOpenChange(false)}
+            disabled={isSubmitting}
+          >
+            Cancel
+          </Button>
+          <Button onClick={handleSubmit} disabled={isSubmitting}>
+            {isSubmitting ? "Submitting..." : "Submit Feedback"}
+          </Button>
+        </DialogFooter>
+      </DialogContent>
+    </Dialog>
+  );
+}
diff --git a/src/components/assistant-ui/AssistantDropzone.tsx b/src/components/assistant-ui/AssistantDropzone.tsx
index 1a12fc71..dccad4fc 100644
--- a/src/components/assistant-ui/AssistantDropzone.tsx
+++ b/src/components/assistant-ui/AssistantDropzone.tsx
@@ -6,6 +6,10 @@ import { useWorkspaceStore } from "@/lib/stores/workspace-store";
 import { Upload } from "lucide-react";
 import { useCallback, useState, useRef } from "react";
 import { toast } from "sonner";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
+import { emitPasswordProtectedPdf } from "@/components/modals/PasswordProtectedPdfDialog";
+import { filterPasswordProtectedPdfs } from "@/lib/uploads/pdf-validation";
+import { isWordFile, isExcelFile, isPptxFile } from "@/lib/uploads/office-document-validation";
 
 interface AssistantDropzoneProps {
   children: React.ReactNode;
@@ -87,11 +91,27 @@ export function AssistantDropzone({ children }: AssistantDropzoneProps) {
         return;
       }
 
+      // Reject password-protected PDFs so other files still upload
+      let filesToAdd = validFiles;
+      const pdfFiles = validFiles.filter((f) => f.type === "application/pdf" || f.name.toLowerCase().endsWith(".pdf"));
+      if (pdfFiles.length > 0) {
+        const { valid: unprotectedPdfs, rejected: protectedNames } = await filterPasswordProtectedPdfs(pdfFiles);
+        if (protectedNames.length > 0) {
+          emitPasswordProtectedPdf(protectedNames);
+        }
+        const nonPdfFiles = validFiles.filter((f) => f.type !== "application/pdf" && !f.name.toLowerCase().endsWith(".pdf"));
+        filesToAdd = [...nonPdfFiles, ...unprotectedPdfs];
+      }
+
+      if (filesToAdd.length === 0) {
+        return;
+      }
+
       isProcessingRef.current = true;
 
       try {
         // Add each file to the composer
-        const addPromises = validFiles.map(async (file) => {
+        const addPromises = filesToAdd.map(async (file) => {
           try {
             await aui.composer().addAttachment(file);
           } catch (error) {
@@ -107,8 +127,8 @@ export function AssistantDropzone({ children }: AssistantDropzoneProps) {
         await Promise.allSettled(addPromises);
 
         // Show success message if some files were rejected
-        if (validFiles.length < acceptedFiles.length) {
-          toast.success(`${validFiles.length} file${validFiles.length > 1 ? 's' : ''} added successfully`, {
+        if (filesToAdd.length < acceptedFiles.length) {
+          toast.success(`${filesToAdd.length} file${filesToAdd.length > 1 ? 's' : ''} added successfully`, {
             style: { color: '#fff' },
           });
         }
@@ -144,12 +164,6 @@ export function AssistantDropzone({ children }: AssistantDropzoneProps) {
       'image/*': ['.png', '.jpg', '.jpeg', '.gif', '.webp', '.svg', '.bmp', '.heic', '.heif', '.avif', '.tiff', '.tif'],
       'video/*': ['.mp4', '.webm', '.avi', '.mov', '.mkv'],
       'application/pdf': ['.pdf'],
-      'application/msword': ['.doc'],
-      'application/vnd.openxmlformats-officedocument.wordprocessingml.document': ['.docx'],
-      'application/vnd.ms-powerpoint': ['.ppt'],
-      'application/vnd.openxmlformats-officedocument.presentationml.presentation': ['.pptx'],
-      'application/vnd.ms-excel': ['.xls'],
-      'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet': ['.xlsx'],
       'text/plain': ['.txt'],
       'text/markdown': ['.md'],
       'text/csv': ['.csv'],
@@ -167,16 +181,24 @@ export function AssistantDropzone({ children }: AssistantDropzoneProps) {
       setIsDragging(false);
       handleDragEnd();
 
-      // Show error for rejected files
       if (fileRejections.length > 0) {
-        const rejectedFileNames = fileRejections.map(rejection => rejection.file.name);
-        toast.error(
-          `The following file${rejectedFileNames.length > 1 ? 's are' : ' is'} not supported:\n${rejectedFileNames.join('\n')}\n\nSupported: Images, Videos, PDFs, Office documents, Text files`,
-          {
-            style: { color: '#fff' },
-            duration: 5000,
-          }
-        );
+        const wordFiles = fileRejections.filter((r) => isWordFile(r.file));
+        const excelFiles = fileRejections.filter((r) => isExcelFile(r.file));
+        const pptxFiles = fileRejections.filter((r) => isPptxFile(r.file));
+        const hasOffice = wordFiles.length > 0 || excelFiles.length > 0 || pptxFiles.length > 0;
+        if (hasOffice) {
+          emitOfficeDocumentRejected({
+            word: wordFiles.length ? wordFiles.map((r) => r.file.name) : undefined,
+            excel: excelFiles.length ? excelFiles.map((r) => r.file.name) : undefined,
+            powerpoint: pptxFiles.length ? pptxFiles.map((r) => r.file.name) : undefined,
+          });
+        } else {
+          const rejectedFileNames = fileRejections.map((r) => r.file.name);
+          toast.error(
+            `The following file${rejectedFileNames.length > 1 ? "s are" : " is"} not supported:\n${rejectedFileNames.join("\n")}\n\nSupported: Images, Videos, PDFs, Text files`,
+            { style: { color: "#fff" }, duration: 5000 }
+          );
+        }
       }
     },
   });
diff --git a/src/components/assistant-ui/PromptBuilderDialog.tsx b/src/components/assistant-ui/PromptBuilderDialog.tsx
index 3570afe6..aaf63b4e 100644
--- a/src/components/assistant-ui/PromptBuilderDialog.tsx
+++ b/src/components/assistant-ui/PromptBuilderDialog.tsx
@@ -428,7 +428,7 @@ export function PromptBuilderDialog({
           </DialogTitle>
         </DialogHeader>
 
-        <div className="space-y-4 py-2 min-w-0 overflow-x-hidden">
+        <div className="space-y-4 py-2 min-w-0">
           {/* Search: Source selector - card style like home action buttons */}
           {config.hasSearchSource && (
             <div className="space-y-2">
@@ -540,7 +540,7 @@ export function PromptBuilderDialog({
 
           {/* Workspace context - separate dialog for picker (scroll works, no layout shift) */}
           {config.hasTopicSelector && items.length > 0 && (
-            <div className="space-y-2 min-w-0 overflow-hidden">
+            <div className="space-y-2 min-w-0">
               <Label>Workspace context</Label>
               <Input
                 placeholder={
diff --git a/src/components/assistant-ui/attachment.tsx b/src/components/assistant-ui/attachment.tsx
index aa1019b2..f17f00b3 100644
--- a/src/components/assistant-ui/attachment.tsx
+++ b/src/components/assistant-ui/attachment.tsx
@@ -29,6 +29,15 @@ import { TooltipIconButton } from "@/components/assistant-ui/tooltip-icon-button
 import { cn } from "@/lib/utils";
 import { useAttachmentUploadStore } from "@/lib/stores/attachment-upload-store";
 import { useUIStore } from "@/lib/stores/ui-store";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
+import { emitPasswordProtectedPdf } from "@/components/modals/PasswordProtectedPdfDialog";
+import {
+  isWordFile,
+  isExcelFile,
+  isPptxFile,
+  isOfficeDocument,
+} from "@/lib/uploads/office-document-validation";
+import { filterPasswordProtectedPdfs } from "@/lib/uploads/pdf-validation";
 import { FaCheck } from "react-icons/fa";
 
 const useFileSrc = (file: File | undefined) => {
@@ -463,7 +472,7 @@ export const ComposerAddAttachment: FC = () => {
 
 
 
-  const handleFileChange = (e: React.ChangeEvent<HTMLInputElement>) => {
+  const handleFileChange = async (e: React.ChangeEvent<HTMLInputElement>) => {
     const files = e.target.files;
     if (!files || files.length === 0) return;
 
@@ -479,25 +488,51 @@ export const ComposerAddAttachment: FC = () => {
         style: { color: '#fff' },
         duration: 5000,
       });
-      // Reset input
-      if (fileInputRef.current) {
-        fileInputRef.current.value = "";
-      }
+      if (fileInputRef.current) fileInputRef.current.value = "";
       return;
     }
 
-    // Validate each file
+    // Validate each file (size + reject Office documents)
     const validFiles: File[] = [];
     const oversizedFiles: string[] = [];
+    const officeWord: string[] = [];
+    const officeExcel: string[] = [];
+    const officePowerpoint: string[] = [];
 
     fileArray.forEach((file) => {
       if (file.size > MAX_FILE_SIZE_BYTES) {
         oversizedFiles.push(`${file.name} (${(file.size / (1024 * 1024)).toFixed(1)}MB)`);
+      } else if (isOfficeDocument(file)) {
+        if (isWordFile(file)) officeWord.push(file.name);
+        else if (isExcelFile(file)) officeExcel.push(file.name);
+        else officePowerpoint.push(file.name);
       } else {
         validFiles.push(file);
       }
     });
 
+    if (officeWord.length > 0 || officeExcel.length > 0 || officePowerpoint.length > 0) {
+      emitOfficeDocumentRejected({
+        word: officeWord.length ? officeWord : undefined,
+        excel: officeExcel.length ? officeExcel : undefined,
+        powerpoint: officePowerpoint.length ? officePowerpoint : undefined,
+      });
+    }
+
+    // Reject password-protected PDFs (so other files still upload)
+    let filesToAdd = validFiles;
+    if (validFiles.length > 0) {
+      const pdfFiles = validFiles.filter((f) => f.type === "application/pdf" || f.name.toLowerCase().endsWith(".pdf"));
+      if (pdfFiles.length > 0) {
+        const { valid: unprotectedPdfs, rejected: protectedNames } = await filterPasswordProtectedPdfs(pdfFiles);
+        if (protectedNames.length > 0) {
+          emitPasswordProtectedPdf(protectedNames);
+        }
+        const nonPdfFiles = validFiles.filter((f) => f.type !== "application/pdf" && !f.name.toLowerCase().endsWith(".pdf"));
+        filesToAdd = [...nonPdfFiles, ...unprotectedPdfs];
+      }
+    }
+
     // Show error for oversized files
     if (oversizedFiles.length > 0) {
       toast.error(
@@ -509,20 +544,19 @@ export const ComposerAddAttachment: FC = () => {
       );
     }
 
-    // Add valid files
-    if (validFiles.length > 0) {
-      validFiles.forEach((file) => {
+    // Add valid files (non–Office-doc, non–password-protected) — others still upload successfully
+    if (filesToAdd.length > 0) {
+      filesToAdd.forEach((file) => {
         aui.composer().addAttachment(file);
       });
 
-      if (validFiles.length < fileArray.length) {
-        toast.success(`${validFiles.length} file${validFiles.length > 1 ? 's' : ''} added successfully`, {
+      if (filesToAdd.length < fileArray.length) {
+        toast.success(`${filesToAdd.length} file${filesToAdd.length > 1 ? 's' : ''} added successfully`, {
           style: { color: '#fff' },
         });
       }
     }
 
-    // Reset input
     if (fileInputRef.current) {
       fileInputRef.current.value = "";
     }
@@ -560,7 +594,7 @@ export const ComposerAddAttachment: FC = () => {
           className="sr-only"
           onChange={handleFileChange}
           multiple={true}
-          accept="image/*,video/*,.pdf,.doc,.docx,.ppt,.pptx,.xls,.xlsx,.txt,.md,.csv,.json,.heic,.heif,.avif,.tiff,.tif"
+          accept="image/*,video/*,.pdf,.txt,.md,.csv,.json,.heic,.heif,.avif,.tiff,.tif"
         />
       </div>
     </>
diff --git a/src/components/assistant-ui/thread.tsx b/src/components/assistant-ui/thread.tsx
index a469f64a..f2ecfb92 100644
--- a/src/components/assistant-ui/thread.tsx
+++ b/src/components/assistant-ui/thread.tsx
@@ -1,5 +1,4 @@
 import {
-  ArrowDownIcon,
   ArrowUpIcon,
   CheckIcon,
   ChevronDown,
@@ -82,6 +81,7 @@ import { WebSearchToolUI } from "@/components/assistant-ui/WebSearchToolUI";
 import { SearchWorkspaceToolUI } from "@/components/assistant-ui/SearchWorkspaceToolUI";
 import { ReadWorkspaceToolUI } from "@/components/assistant-ui/ReadWorkspaceToolUI";
 import { MagicFetchToolUI } from "@/components/assistant-ui/MagicFetchToolUI";
+import { AIFeedbackDialog } from "@/components/assistant-ui/AIFeedbackDialog";
 
 import { DeleteCardToolUI } from "@/components/assistant-ui/DeleteCardToolUI";
 import { TooltipIconButton } from "@/components/assistant-ui/tooltip-icon-button";
@@ -111,6 +111,7 @@ import { DropdownMenuSeparator, DropdownMenuLabel, DropdownMenuSub, DropdownMenu
 import { useShallow } from "zustand/react/shallow";
 import { useWorkspaceState } from "@/hooks/workspace/use-workspace-state";
 import { useWorkspaceOperations } from "@/hooks/workspace/use-workspace-operations";
+import { useFeatureFlagEnabled } from "posthog-js/react";
 import { toast } from "sonner";
 import { useCreateCardFromMessage } from "@/hooks/ai/use-create-card-from-message";
 import { extractUrls, createUrlFile } from "@/lib/attachments/url-utils";
@@ -230,10 +231,6 @@ export const Thread: FC<ThreadProps> = ({ items = [] }) => {
                 AssistantMessage,
               }}
             />
-
-            <div className="sticky bottom-4 z-10 flex justify-center pt-4">
-              <ThreadScrollToBottom />
-            </div>
           </ThreadPrimitive.Viewport>
 
           <div className="aui-thread-composer-wrapper mx-auto flex w-full max-w-[var(--thread-max-width)] flex-shrink-0 flex-col gap-4 overflow-visible rounded-t-3xl bg-sidebar px-4 pb-3 md:pb-4">
@@ -245,26 +242,6 @@ export const Thread: FC<ThreadProps> = ({ items = [] }) => {
   );
 };
 
-const ThreadScrollToBottom: FC = () => {
-  return (
-    <ThreadPrimitive.ScrollToBottom asChild>
-      <TooltipIconButton
-        tooltip="Scroll to bottom"
-        variant="outline"
-        className={cn(
-          "aui-thread-scroll-to-bottom rounded-xl p-4 disabled:hidden",
-          "bg-white/5 border-white/10 text-white/60",
-          "hover:border-white/20 hover:bg-white/10 hover:text-white",
-          "shadow-none",
-          "transition-[background-color,border-color,box-shadow,color] duration-300 ease-out"
-        )}
-      >
-        <ArrowDownIcon />
-      </TooltipIconButton>
-    </ThreadPrimitive.ScrollToBottom>
-  );
-};
-
 const ThreadLoadingSkeleton: FC = () => {
   return (
     <div
@@ -1014,6 +991,12 @@ const ComposerAction: FC<ComposerActionProps> = ({ items }) => {
 
   const [isWarningPopoverOpen, setIsWarningPopoverOpen] = useState(false);
   const hoverTimeoutRef = useRef<NodeJS.Timeout | null>(null);
+  const [isFeedbackDialogOpen, setIsFeedbackDialogOpen] = useState(false);
+
+  // AI Debug button: always show in dev, only when feature flag enabled in prod
+  const isDev = process.env.NODE_ENV === "development";
+  const aiDebugFlagEnabled = useFeatureFlagEnabled("ai-debug-feedback");
+  const showAiDebugButton = isDev || aiDebugFlagEnabled === true;
 
   // Model selector state
   const selectedModelId = useUIStore((state) => state.selectedModelId);
@@ -1099,19 +1082,24 @@ const ComposerAction: FC<ComposerActionProps> = ({ items }) => {
             ))}
           </DropdownMenuContent>
         </DropdownMenu>
-        {/* AI Debug Button - only in development */}
-        {process.env.NODE_ENV === "development" && (
+        {/* AI Debug Button - feature flag in prod, localhost debugger in dev */}
+        {showAiDebugButton && (
           <button
             type="button"
             className="flex items-center gap-1.5 px-1.5 py-1 rounded-md bg-red-500/10 hover:bg-red-500/20 transition-colors flex-shrink-0 text-xs font-normal text-red-500 hover:text-red-400 cursor-pointer border border-red-500/20"
             onClick={() => {
-              window.open("http://localhost:4983", "_blank");
+              if (process.env.NODE_ENV === "development") {
+                window.open("http://localhost:4983", "_blank");
+              } else {
+                setIsFeedbackDialogOpen(true);
+              }
             }}
           >
             <Bug className="w-3.5 h-3.5" />
             <span>AI Debug</span>
           </button>
         )}
+        <AIFeedbackDialog open={isFeedbackDialogOpen} onOpenChange={setIsFeedbackDialogOpen} />
         {/* Warning icon for anonymous users */}
         {isAnonymous && (
 
@@ -1242,7 +1230,7 @@ const AssistantMessage: FC = () => {
   return (
     <MessagePrimitive.Root asChild>
       <div
-        className="aui-assistant-message-root relative mx-auto w-full max-w-[var(--thread-max-width)] animate-in pb-4 duration-150 ease-out fade-in slide-in-from-bottom-1 last:mb-24"
+        className="aui-assistant-message-root relative mx-auto w-full max-w-[var(--thread-max-width)] animate-in pb-4 duration-150 ease-out fade-in slide-in-from-bottom-1 last:mb-4"
         data-role="assistant"
       >
         <div className="aui-assistant-message-content mx-2 leading-7 break-words text-foreground">
diff --git a/src/components/assistant-ui/tool-group.tsx b/src/components/assistant-ui/tool-group.tsx
index 76080498..dfa28481 100644
--- a/src/components/assistant-ui/tool-group.tsx
+++ b/src/components/assistant-ui/tool-group.tsx
@@ -225,6 +225,12 @@ const ToolGroupImpl: FC<
     [isToolGroupStreaming],
   );
 
+  // Only group when there are more than 1 consecutive tool call.
+  // IMPORTANT: this check must stay *after* hooks to avoid conditional hook calls.
+  if (toolCount <= 1) {
+    return <>{children}</>;
+  }
+
   return (
     <ToolGroupRoot variant="ghost" open={isOpen} onOpenChange={handleOpenChange}>
       <ToolGroupTrigger count={toolCount} active={isToolGroupStreaming} />
diff --git a/src/components/home/HomeHeroDropzone.tsx b/src/components/home/HomeHeroDropzone.tsx
index 3844823b..8aef6ece 100644
--- a/src/components/home/HomeHeroDropzone.tsx
+++ b/src/components/home/HomeHeroDropzone.tsx
@@ -5,6 +5,12 @@ import { useHomeAttachments } from "@/contexts/HomeAttachmentsContext";
 import { Upload } from "lucide-react";
 import { useCallback } from "react";
 import { toast } from "sonner";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
+import {
+  isWordFile,
+  isExcelFile,
+  isPptxFile,
+} from "@/lib/uploads/office-document-validation";
 import { cn } from "@/lib/utils";
 
 interface HomeHeroDropzoneProps {
@@ -61,8 +67,20 @@ export function HomeHeroDropzone({ children, onFilesDropped }: HomeHeroDropzoneP
     },
     onDropRejected: (fileRejections) => {
       if (fileRejections.length > 0) {
-        const names = fileRejections.map((r) => r.file.name).join(", ");
-        toast.error(`Only PDF, image, and audio files are supported. Rejected: ${names}`);
+        const wordFiles = fileRejections.filter((r) => isWordFile(r.file));
+        const excelFiles = fileRejections.filter((r) => isExcelFile(r.file));
+        const pptxFiles = fileRejections.filter((r) => isPptxFile(r.file));
+        const hasOffice = wordFiles.length > 0 || excelFiles.length > 0 || pptxFiles.length > 0;
+        if (hasOffice) {
+          emitOfficeDocumentRejected({
+            word: wordFiles.length ? wordFiles.map((r) => r.file.name) : undefined,
+            excel: excelFiles.length ? excelFiles.map((r) => r.file.name) : undefined,
+            powerpoint: pptxFiles.length ? pptxFiles.map((r) => r.file.name) : undefined,
+          });
+        } else {
+          const names = fileRejections.map((r) => r.file.name).join(", ");
+          toast.error(`Only PDF, image, and audio files are supported. Rejected: ${names}`);
+        }
       }
     },
   });
diff --git a/src/components/home/WorkspaceGrid.tsx b/src/components/home/WorkspaceGrid.tsx
index 5a8d1a68..25f56373 100644
--- a/src/components/home/WorkspaceGrid.tsx
+++ b/src/components/home/WorkspaceGrid.tsx
@@ -1,13 +1,12 @@
 "use client";
 
-import { useState, useEffect, useRef, useMemo } from "react";
+import { useState, useRef, useMemo } from "react";
 import { createPortal } from "react-dom";
 import { useRouter } from "next/navigation";
 import { FolderPlus, MoreVertical, Users, Trash2, Share2, X, CheckSquare } from "lucide-react";
 import { useUIStore } from "@/lib/stores/ui-store";
 import { useWorkspaceContext } from "@/contexts/WorkspaceContext";
 import CreateWorkspaceModal from "@/components/workspace/CreateWorkspaceModal";
-import { useSession } from "@/lib/auth-client";
 import { IconRenderer } from "@/hooks/use-icon-picker";
 import { cn } from "@/lib/utils";
 import WorkspaceSettingsModal from "@/components/workspace/WorkspaceSettingsModal";
@@ -29,7 +28,6 @@ export function WorkspaceGrid({ searchQuery = "" }: WorkspaceGridProps) {
   const router = useRouter();
   const { showCreateWorkspaceModal, setShowCreateWorkspaceModal } = useUIStore();
   const { workspaces, switchWorkspace, loadWorkspaces, deleteWorkspace, loadingWorkspaces } = useWorkspaceContext();
-  const { data: session } = useSession();
   const [showSettingsModal, setShowSettingsModal] = useState(false);
   const [showShareDialog, setShowShareDialog] = useState(false);
 
@@ -45,8 +43,6 @@ export function WorkspaceGrid({ searchQuery = "" }: WorkspaceGridProps) {
     );
   }, [workspaces, searchQuery]);
   const [settingsWorkspace, setSettingsWorkspace] = useState<WorkspaceWithState | null>(null);
-  const [isCreatingWorkspace, setIsCreatingWorkspace] = useState(false);
-  const hasAttemptedWelcomeWorkspace = useRef(false);
   const prefetchTimeoutRef = useRef<NodeJS.Timeout | null>(null);
 
   // Multi-select state
@@ -100,36 +96,6 @@ export function WorkspaceGrid({ searchQuery = "" }: WorkspaceGridProps) {
     }
   };
 
-  // Lazy workspace creation for anonymous users
-  useEffect(() => {
-    const createWelcomeWorkspace = async () => {
-      if (!session?.user?.isAnonymous) return;
-      if (workspaces.length > 0) return; // Already has workspaces
-      if (isCreatingWorkspace) return; // Already creating
-      if (hasAttemptedWelcomeWorkspace.current) return; // Avoid retry loop
-
-      setIsCreatingWorkspace(true);
-      hasAttemptedWelcomeWorkspace.current = true;
-      try {
-        console.log("Welcome workspace creation disabled");
-        // const res = await fetch("/api/guest/create-welcome-workspace", {
-        //   method: "POST",
-        // });
-
-        // if (res.ok) {
-        //   // Reload workspaces to show the newly created one
-        //   await loadWorkspaces();
-        // }
-      } catch (error) {
-        console.error("Failed to create welcome workspace:", error);
-      } finally {
-        setIsCreatingWorkspace(false);
-      }
-    };
-
-    createWelcomeWorkspace();
-  }, [session, workspaces.length, loadWorkspaces]);
-
   // Format date helper
   const formatDate = (dateString: string | null | undefined) => {
     if (!dateString) return "";
@@ -206,14 +172,6 @@ export function WorkspaceGrid({ searchQuery = "" }: WorkspaceGridProps) {
             </h3>
           </div>
 
-          {/* Loading state for anonymous users creating first workspace */}
-          {session?.user?.isAnonymous && workspaces.length === 0 && isCreatingWorkspace && (
-            <div className="relative rounded-md shadow-sm min-h-[180px] overflow-hidden flex flex-col items-center justify-center gap-3 bg-muted/40 border border-muted-foreground/20">
-              <div className="w-8 h-8 border-2 border-primary/30 border-t-primary animate-spin rounded-full" />
-              <p className="text-sm text-muted-foreground">Setting up your workspace...</p>
-            </div>
-          )}
-
           {/* Existing Workspaces */}
           {filteredWorkspaces.map((workspace) => {
             const color = workspace.color as CardColor | undefined;
diff --git a/src/components/layout/SessionHandler.tsx b/src/components/layout/SessionHandler.tsx
index f85fe644..9fc1e31d 100644
--- a/src/components/layout/SessionHandler.tsx
+++ b/src/components/layout/SessionHandler.tsx
@@ -5,9 +5,8 @@ import { useSession, signIn } from "@/lib/auth-client";
 import { SidebarProvider } from "@/components/ui/sidebar";
 
 /**
- * Handles anonymous session creation and workspace access.
- * Creates anonymous session if needed, workspace creation happens lazily in WorkspaceGrid.
- * No loading screen - renders children immediately.
+ * Handles anonymous session creation.
+ * Creates anonymous session if needed. No loading screen - renders children immediately.
  */
 export function AnonymousSessionHandler({ children }: { children: React.ReactNode }) {
   const { data: session, isPending } = useSession();
diff --git a/src/components/modals/OfficeDocumentRejectedDialog.tsx b/src/components/modals/OfficeDocumentRejectedDialog.tsx
new file mode 100644
index 00000000..fba26ff8
--- /dev/null
+++ b/src/components/modals/OfficeDocumentRejectedDialog.tsx
@@ -0,0 +1,152 @@
+"use client";
+
+import { useState, useEffect, useCallback } from "react";
+import {
+  Dialog,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from "@/components/ui/dialog";
+import { Button } from "@/components/ui/button";
+import { FileWarning, ExternalLink } from "lucide-react";
+import { CONVERT_URLS } from "@/lib/uploads/office-document-validation";
+
+export interface OfficeDocumentRejectedEvent {
+  word?: string[];
+  excel?: string[];
+  powerpoint?: string[];
+}
+
+type Listener = (e: OfficeDocumentRejectedEvent) => void;
+const listeners = new Set<Listener>();
+
+export function emitOfficeDocumentRejected(event: OfficeDocumentRejectedEvent) {
+  if (
+    (!event.word || event.word.length === 0) &&
+    (!event.excel || event.excel.length === 0) &&
+    (!event.powerpoint || event.powerpoint.length === 0)
+  ) {
+    return;
+  }
+  listeners.forEach((fn) => fn(event));
+}
+
+const SECTIONS: Array<{
+  key: keyof OfficeDocumentRejectedEvent;
+  label: string;
+  extLabel: string;
+  convertUrl: string;
+}> = [
+  {
+    key: "word",
+    label: "Word",
+    extLabel: ".doc, .docx",
+    convertUrl: CONVERT_URLS.word,
+  },
+  {
+    key: "excel",
+    label: "Excel",
+    extLabel: ".xls, .xlsx",
+    convertUrl: CONVERT_URLS.excel,
+  },
+  {
+    key: "powerpoint",
+    label: "PowerPoint",
+    extLabel: ".ppt, .pptx",
+    convertUrl: CONVERT_URLS.powerpoint,
+  },
+];
+
+/**
+ * Global dialog for rejected Office documents (Word, Excel, PowerPoint).
+ * Links users to iLovePDF to convert to PDF.
+ */
+export function OfficeDocumentRejectedDialog() {
+  const [open, setOpen] = useState(false);
+  const [event, setEvent] = useState<OfficeDocumentRejectedEvent>({});
+
+  const handleEvent = useCallback((e: OfficeDocumentRejectedEvent) => {
+    setEvent(e);
+    setOpen(true);
+  }, []);
+
+  useEffect(() => {
+    listeners.add(handleEvent);
+    return () => {
+      listeners.delete(handleEvent);
+    };
+  }, [handleEvent]);
+
+  const sections = SECTIONS.filter((s) => {
+    const names = event[s.key];
+    return names && names.length > 0;
+  });
+
+  const totalCount = sections.reduce(
+    (sum, s) => sum + (event[s.key]?.length ?? 0),
+    0
+  );
+
+  const title =
+    sections.length === 1
+      ? `${sections[0].label}${(event[sections[0].key]?.length ?? 0) > 1 ? " files" : " file"} not supported`
+      : `${totalCount} Office files not supported`;
+
+  const description =
+    sections.length === 1
+      ? `We don't support ${sections[0].label} (${sections[0].extLabel}) files. Convert to PDF first, then upload.`
+      : "We don't support Word, Excel, or PowerPoint files. Convert them to PDF first, then upload.";
+
+  return (
+    <Dialog open={open} onOpenChange={setOpen}>
+      <DialogContent className="sm:max-w-md">
+        <DialogHeader>
+          <DialogTitle className="flex items-center gap-2">
+            <FileWarning className="size-5 text-destructive" />
+            {title}
+          </DialogTitle>
+          <DialogDescription>{description}</DialogDescription>
+        </DialogHeader>
+
+        <div className="space-y-3 py-1">
+          {sections.map((section) => {
+            const names = event[section.key] ?? [];
+            return (
+              <div
+                key={section.key}
+                className="rounded-md border bg-muted/50 p-3"
+              >
+                <p className="text-sm font-medium mb-1">
+                  {section.label} ({names.length})
+                </p>
+                <ul className="text-sm text-muted-foreground space-y-0.5">
+                  {names.map((name, i) => (
+                    <li key={`${section.key}-${i}-${name}`} className="truncate">
+                      {name}
+                    </li>
+                  ))}
+                </ul>
+                <Button asChild variant="link" className="h-auto p-0 mt-2 text-xs">
+                  <a
+                    href={section.convertUrl}
+                    target="_blank"
+                    rel="noopener noreferrer"
+                  >
+                    Convert {section.label} to PDF
+                    <ExternalLink className="ml-1 inline size-3" />
+                  </a>
+                </Button>
+              </div>
+            );
+          })}
+        </div>
+
+        <DialogFooter>
+          <Button onClick={() => setOpen(false)}>Close</Button>
+        </DialogFooter>
+      </DialogContent>
+    </Dialog>
+  );
+}
diff --git a/src/components/modals/PasswordProtectedPdfDialog.tsx b/src/components/modals/PasswordProtectedPdfDialog.tsx
index 8f2c7c6c..504361f3 100644
--- a/src/components/modals/PasswordProtectedPdfDialog.tsx
+++ b/src/components/modals/PasswordProtectedPdfDialog.tsx
@@ -82,7 +82,7 @@ export function PasswordProtectedPdfDialog() {
           <Button variant="outline" onClick={() => setOpen(false)}>
             Close
           </Button>
-          <Button asChild>
+          <Button asChild onClick={() => setOpen(false)}>
             <a href={UNLOCK_URL} target="_blank" rel="noopener noreferrer">
               Unlock PDF
               <ExternalLink className="ml-2 size-4" />
diff --git a/src/components/modals/UploadDialog.tsx b/src/components/modals/UploadDialog.tsx
index e1c91df3..8b7bfbe1 100644
--- a/src/components/modals/UploadDialog.tsx
+++ b/src/components/modals/UploadDialog.tsx
@@ -19,6 +19,12 @@ import { cn } from "@/lib/utils";
 import { uploadFileDirect } from "@/lib/uploads/client-upload";
 import { filterPasswordProtectedPdfs } from "@/lib/uploads/pdf-validation";
 import { emitPasswordProtectedPdf } from "@/components/modals/PasswordProtectedPdfDialog";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
+import {
+  isWordFile,
+  isExcelFile,
+  isPptxFile,
+} from "@/lib/uploads/office-document-validation";
 
 interface UploadDialogProps {
     open: boolean;
@@ -227,6 +233,21 @@ export function UploadDialog({
             'application/pdf': ['.pdf'],
         },
         disabled: isUploading,
+        onDropRejected: (fileRejections) => {
+            if (fileRejections.length > 0) {
+                const wordFiles = fileRejections.filter((r) => isWordFile(r.file));
+                const excelFiles = fileRejections.filter((r) => isExcelFile(r.file));
+                const pptxFiles = fileRejections.filter((r) => isPptxFile(r.file));
+                const hasOffice = wordFiles.length > 0 || excelFiles.length > 0 || pptxFiles.length > 0;
+                if (hasOffice) {
+                    emitOfficeDocumentRejected({
+                        word: wordFiles.length ? wordFiles.map((r) => r.file.name) : undefined,
+                        excel: excelFiles.length ? excelFiles.map((r) => r.file.name) : undefined,
+                        powerpoint: pptxFiles.length ? pptxFiles.map((r) => r.file.name) : undefined,
+                    });
+                }
+            }
+        },
     });
 
     const handleKeyDown = useCallback((e: React.KeyboardEvent) => {
diff --git a/src/components/pdf/AppPdfViewer.tsx b/src/components/pdf/AppPdfViewer.tsx
index c7904b58..84b694dd 100644
--- a/src/components/pdf/AppPdfViewer.tsx
+++ b/src/components/pdf/AppPdfViewer.tsx
@@ -972,7 +972,7 @@ const AppPdfViewer = ({ pdfSrc, showThumbnails = false, renderHeader, itemName,
 
                   {/* Error state (including password required) */}
                   {isError && (
-                    <div className="w-full h-full" style={{ minHeight: '300px', backgroundColor: '#1a1a1a' }}>
+                    <div className="w-full h-full" style={{ minHeight: '300px', backgroundColor: 'var(--sidebar)' }}>
                       <PdfPasswordPrompt documentState={documentState} pdfSrc={pdfSrc} />
                     </div>
                   )}
@@ -1025,7 +1025,7 @@ const AppPdfViewer = ({ pdfSrc, showThumbnails = false, renderHeader, itemName,
                           <Viewport
                             documentId={activeDocumentId}
                             className="w-full h-full"
-                            style={{ backgroundColor: '#1a1a1a' }}
+                            style={{ backgroundColor: 'var(--sidebar)' }}
                           >
                             <ZoomGestureWrapper documentId={activeDocumentId}>
                               <Scroller
diff --git a/src/components/pdf/LightweightPdfPreview.tsx b/src/components/pdf/LightweightPdfPreview.tsx
index 9ef314bf..e108a0d2 100644
--- a/src/components/pdf/LightweightPdfPreview.tsx
+++ b/src/components/pdf/LightweightPdfPreview.tsx
@@ -249,7 +249,7 @@ function PdfSnapshotRenderer({
 
     if (isRendering) {
         return (
-            <div className={`flex items-center justify-center bg-[#1a1a1a] ${className || ''}`}>
+            <div className={`flex items-center justify-center bg-sidebar ${className || ''}`}>
                 <div className="flex items-center gap-2 text-white/40">
                     <Loader2 size={16} className="animate-spin" />
                     <span className="text-xs">Rendering...</span>
@@ -260,14 +260,14 @@ function PdfSnapshotRenderer({
 
     if (!imageUrl) {
         return (
-            <div className={`flex items-center justify-center bg-[#1a1a1a] ${className || ''}`}>
+            <div className={`flex items-center justify-center bg-sidebar ${className || ''}`}>
                 <div className="text-white/40 text-xs">PDF Preview</div>
             </div>
         );
     }
 
     return (
-        <div className={`relative overflow-hidden bg-[#1a1a1a] flex justify-center ${className || ''}`}>
+        <div className={`relative overflow-hidden bg-sidebar flex justify-center ${className || ''}`}>
             <div
                 className="h-full"
                 style={{
@@ -329,7 +329,7 @@ export function LightweightPdfPreview({ pdfSrc, title, className }: LightweightP
 
     if (engineLoading || !engine) {
         return (
-            <div className={`flex items-center justify-center bg-[#1a1a1a] ${className || ''}`}>
+            <div className={`flex items-center justify-center bg-sidebar ${className || ''}`}>
                 <div className="flex items-center gap-2 text-white/40">
                     <Loader2 size={16} className="animate-spin" />
                     <span className="text-xs">Loading...</span>
@@ -346,7 +346,7 @@ export function LightweightPdfPreview({ pdfSrc, title, className }: LightweightP
                         {({ isLoading, isLoaded, documentState }) => (
                             <>
                                 {isLoading && (
-                                    <div className={`flex items-center justify-center bg-[#1a1a1a] ${className || ''}`}>
+                                    <div className={`flex items-center justify-center bg-sidebar ${className || ''}`}>
                                         <div className="flex items-center gap-2 text-white/40">
                                             <Loader2 size={16} className="animate-spin" />
                                             <span className="text-xs">Loading PDF...</span>
@@ -366,7 +366,7 @@ export function LightweightPdfPreview({ pdfSrc, title, className }: LightweightP
                         )}
                     </DocumentContent>
                 ) : (
-                    <div className={`flex items-center justify-center bg-[#1a1a1a] ${className || ''}`}>
+                    <div className={`flex items-center justify-center bg-sidebar ${className || ''}`}>
                         <div className="flex items-center gap-2 text-white/40">
                             <Loader2 size={16} className="animate-spin" />
                             <span className="text-xs">Initializing...</span>
diff --git a/src/components/pdf/PdfPanelHeader.tsx b/src/components/pdf/PdfPanelHeader.tsx
index a7534372..10c07908 100644
--- a/src/components/pdf/PdfPanelHeader.tsx
+++ b/src/components/pdf/PdfPanelHeader.tsx
@@ -19,6 +19,7 @@ import ChatFloatingButton from "@/components/chat/ChatFloatingButton";
 import { useUIStore } from "@/lib/stores/ui-store";
 import { useAui } from "@assistant-ui/react";
 import { toast } from "sonner";
+import { focusComposerInput } from "@/lib/utils/composer-utils";
 
 // PDF Plugin imports
 import { useZoom, ZoomMode } from '@embedpdf/plugin-zoom/react';
@@ -114,6 +115,10 @@ export const PdfPanelHeader = memo(function PdfPanelHeader({
                 // Turn off capture mode
                 captureRef.current?.toggleMarqueeCapture();
 
+                // Focus composer similar to reply flow — expand chat if collapsed, then focus input
+                useUIStore.getState().setIsChatExpanded(true);
+                focusComposerInput();
+
             } catch (error) {
                 console.error("Failed to add capture attachment:", error);
                 toast.error("Failed to add screenshot");
diff --git a/src/components/providers.tsx b/src/components/providers.tsx
index e509062f..2140b2cc 100644
--- a/src/components/providers.tsx
+++ b/src/components/providers.tsx
@@ -4,6 +4,7 @@ import { useRouter } from "next/navigation";
 import { Toaster } from "@/components/ui/sonner";
 import { PostHogIdentify } from "./providers/PostHogIdentify";
 import { PasswordProtectedPdfDialog } from "@/components/modals/PasswordProtectedPdfDialog";
+import { OfficeDocumentRejectedDialog } from "@/components/modals/OfficeDocumentRejectedDialog";
 import { TooltipProvider } from "@/components/ui/tooltip";
 
 export function Providers({ children }: { children: React.ReactNode }) {
@@ -14,6 +15,7 @@ export function Providers({ children }: { children: React.ReactNode }) {
       <PostHogIdentify />
       {children}
       <PasswordProtectedPdfDialog />
+      <OfficeDocumentRejectedDialog />
       <Toaster
         position="top-right"
         richColors
diff --git a/src/components/ui/command.tsx b/src/components/ui/command.tsx
index 8cb4ca7a..312e777f 100644
--- a/src/components/ui/command.tsx
+++ b/src/components/ui/command.tsx
@@ -35,12 +35,14 @@ function CommandDialog({
   children,
   className,
   showCloseButton = true,
+  shouldFilter,
   ...props
 }: React.ComponentProps<typeof Dialog> & {
   title?: string
   description?: string
   className?: string
   showCloseButton?: boolean
+  shouldFilter?: boolean
 }) {
   return (
     <Dialog {...props}>
@@ -52,7 +54,10 @@ function CommandDialog({
         className={cn("overflow-hidden p-0", className)}
         showCloseButton={showCloseButton}
       >
-        <Command className="[&_[cmdk-group-heading]]:text-muted-foreground **:data-[slot=command-input-wrapper]:h-12 [&_[cmdk-group-heading]]:px-2 [&_[cmdk-group-heading]]:font-medium [&_[cmdk-group]]:px-2 [&_[cmdk-group]:not([hidden])_~[cmdk-group]]:pt-0 [&_[cmdk-input-wrapper]_svg]:h-5 [&_[cmdk-input-wrapper]_svg]:w-5 [&_[cmdk-input]]:h-12 [&_[cmdk-item]]:px-2 [&_[cmdk-item]]:py-3 [&_[cmdk-item]_svg]:h-5 [&_[cmdk-item]_svg]:w-5">
+        <Command
+          shouldFilter={shouldFilter}
+          className="[&_[cmdk-group-heading]]:text-muted-foreground **:data-[slot=command-input-wrapper]:h-12 [&_[cmdk-group-heading]]:px-2 [&_[cmdk-group-heading]]:font-medium [&_[cmdk-group]]:px-2 [&_[cmdk-group]:not([hidden])_~[cmdk-group]]:pt-0 [&_[cmdk-input-wrapper]_svg]:h-5 [&_[cmdk-input-wrapper]_svg]:w-5 [&_[cmdk-input]]:h-12 [&_[cmdk-item]]:px-2 [&_[cmdk-item]]:py-3 [&_[cmdk-item]_svg]:h-5 [&_[cmdk-item]_svg]:w-5"
+        >
           {children}
         </Command>
       </DialogContent>
diff --git a/src/components/ui/resizable.tsx b/src/components/ui/resizable.tsx
index 50a93049..33c135f3 100644
--- a/src/components/ui/resizable.tsx
+++ b/src/components/ui/resizable.tsx
@@ -39,7 +39,13 @@ function ResizableHandle({
     <Separator
       data-slot="resizable-handle"
       className={cn(
-        "focus-visible:ring-ring relative flex w-px items-center justify-center after:absolute after:inset-y-0 after:left-1/2 after:w-1 after:-translate-x-1/2 focus-visible:ring-1 focus-visible:ring-offset-1 focus-visible:outline-hidden data-[orientation=vertical]:h-px data-[orientation=vertical]:w-full data-[orientation=vertical]:after:left-0 data-[orientation=vertical]:after:h-1 data-[orientation=vertical]:after:w-full data-[orientation=vertical]:after:translate-x-0 data-[orientation=vertical]:after:-translate-y-1/2 [&[data-orientation=vertical]>div]:rotate-90",
+        "relative z-30 flex w-px items-center justify-center outline-none data-[orientation=vertical]:h-px data-[orientation=vertical]:w-full [&[data-orientation=vertical]>div]:rotate-90",
+        "border-transparent dark:border-sidebar-border",
+        "[&[data-separator=hover]]:border-muted-foreground [&[data-separator=active]]:border-muted-foreground",
+        "[&[data-separator=hover]:not([data-orientation=vertical])]:shadow-[0.5px_0_0_0_var(--muted-foreground),-0.5px_0_0_0_var(--muted-foreground)]",
+        "[&[data-separator=hover][data-orientation=vertical]]:shadow-[0_0.5px_0_0_var(--muted-foreground),0_-0.5px_0_0_var(--muted-foreground)]",
+        "[&[data-separator=active]:not([data-orientation=vertical])]:shadow-[0.5px_0_0_0_var(--muted-foreground),-0.5px_0_0_0_var(--muted-foreground)]",
+        "[&[data-separator=active][data-orientation=vertical]]:shadow-[0_0.5px_0_0_var(--muted-foreground),0_-0.5px_0_0_var(--muted-foreground)]",
         className
       )}
       {...props}
diff --git a/src/components/ui/sidebar.tsx b/src/components/ui/sidebar.tsx
index 48fc8b52..d999d25c 100644
--- a/src/components/ui/sidebar.tsx
+++ b/src/components/ui/sidebar.tsx
@@ -239,7 +239,7 @@ function Sidebar({
           // Adjust the padding for floating and inset variants.
           variant === "floating" || variant === "inset"
             ? "p-2 group-data-[collapsible=icon]:w-[calc(var(--sidebar-width-icon)+(--spacing(4))+2px)]"
-            : "group-data-[collapsible=icon]:w-(--sidebar-width-icon) group-data-[side=left]:border-r group-data-[side=right]:border-l border-sidebar-border",
+            : "group-data-[collapsible=icon]:w-(--sidebar-width-icon) group-data-[side=right]:border-l border-sidebar-border",
           className
         )}
         {...props}
diff --git a/src/components/workspace-canvas/WorkspaceCanvasDropzone.tsx b/src/components/workspace-canvas/WorkspaceCanvasDropzone.tsx
index 1a8726b8..6744e7c5 100644
--- a/src/components/workspace-canvas/WorkspaceCanvasDropzone.tsx
+++ b/src/components/workspace-canvas/WorkspaceCanvasDropzone.tsx
@@ -13,7 +13,13 @@ import { useReactiveNavigation } from "@/hooks/ui/use-reactive-navigation";
 import { uploadFileDirect } from "@/lib/uploads/client-upload";
 import { uploadPdfToStorage } from "@/lib/uploads/pdf-upload-with-ocr";
 import { filterPasswordProtectedPdfs } from "@/lib/uploads/pdf-validation";
+import {
+  isWordFile,
+  isExcelFile,
+  isPptxFile,
+} from "@/lib/uploads/office-document-validation";
 import { emitPasswordProtectedPdf } from "@/components/modals/PasswordProtectedPdfDialog";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
 
 interface WorkspaceCanvasDropzoneProps {
   children: React.ReactNode;
@@ -516,16 +522,24 @@ export function WorkspaceCanvasDropzone({ children }: WorkspaceCanvasDropzonePro
       setIsDragging(false);
       handleDragEnd();
 
-      // Show error for rejected files
       if (fileRejections.length > 0) {
-        const rejectedFileNames = fileRejections.map(rejection => rejection.file.name);
-        toast.error(
-          `Only PDF, image, and audio files can be dropped.\nRejected: ${rejectedFileNames.join(', ')}`,
-          {
-            style: { color: '#fff' },
-            duration: 5000,
-          }
-        );
+        const wordFiles = fileRejections.filter((r) => isWordFile(r.file));
+        const excelFiles = fileRejections.filter((r) => isExcelFile(r.file));
+        const pptxFiles = fileRejections.filter((r) => isPptxFile(r.file));
+        const hasOffice = wordFiles.length > 0 || excelFiles.length > 0 || pptxFiles.length > 0;
+        if (hasOffice) {
+          emitOfficeDocumentRejected({
+            word: wordFiles.length ? wordFiles.map((r) => r.file.name) : undefined,
+            excel: excelFiles.length ? excelFiles.map((r) => r.file.name) : undefined,
+            powerpoint: pptxFiles.length ? pptxFiles.map((r) => r.file.name) : undefined,
+          });
+        } else {
+          const rejectedFileNames = fileRejections.map((r) => r.file.name);
+          toast.error(
+            `Only PDF, image, and audio files can be dropped.\nRejected: ${rejectedFileNames.join(", ")}`,
+            { style: { color: "#fff" }, duration: 5000 }
+          );
+        }
       }
     },
   });
diff --git a/src/components/workspace-canvas/WorkspaceContent.tsx b/src/components/workspace-canvas/WorkspaceContent.tsx
index 2126d6df..252a4d4b 100644
--- a/src/components/workspace-canvas/WorkspaceContent.tsx
+++ b/src/components/workspace-canvas/WorkspaceContent.tsx
@@ -5,7 +5,7 @@ import { useWorkspaceStore } from "@/lib/stores/workspace-store";
 import { Plus, Copy, Check, Download, Upload } from "lucide-react";
 import { EmptyState } from "@/components/empty-state";
 import type { AgentState, Item, CardType } from "@/lib/workspace-state/types";
-import { filterItems } from "@/lib/workspace-state/search";
+import { filterItemsByFolder } from "@/lib/workspace-state/search";
 import { useAutoScroll } from "@/hooks/ui/use-auto-scroll";
 import { WorkspaceGrid } from "./WorkspaceGrid";
 import type { LayoutItem } from "react-grid-layout";
@@ -22,7 +22,6 @@ interface WorkspaceContentProps {
   deleteItem: (itemId: string) => void;
   updateAllItems: (items: Item[]) => void;
   getStatePreviewJSON: (s: AgentState | undefined) => Record<string, unknown>;
-  searchQuery?: string;
   columns: number; // Pass columns from layout state instead of calculating here
   setOpenModalItemId: (id: string | null) => void;
   scrollContainerRef?: React.RefObject<HTMLDivElement | null>;
@@ -47,7 +46,6 @@ export default function WorkspaceContent({
   deleteItem,
   updateAllItems,
   getStatePreviewJSON,
-  searchQuery = "",
   columns, // Columns now passed from parent (calculated in use-layout-state)
   setOpenModalItemId,
   scrollContainerRef: externalScrollContainerRef,
@@ -130,10 +128,10 @@ export default function WorkspaceContent({
     }
   }, [viewState, getStatePreviewJSON, workspaceTitle]);
 
-  // Filter items based on search query and active folder
+  // Filter items by active folder (search is handled by WorkspaceSearchDialog)
   const filteredItems = useMemo(() => {
-    return filterItems(viewState.items, searchQuery, activeFolderId);
-  }, [viewState.items, searchQuery, activeFolderId]);
+    return filterItemsByFolder(viewState.items ?? [], activeFolderId ?? null);
+  }, [viewState.items, activeFolderId]);
 
   // Handle opening a folder (folders are now items with type: 'folder')
   // Uses setActiveFolderId to switch folder without closing panels; breadcrumb handles "navigate back"
@@ -175,7 +173,6 @@ export default function WorkspaceContent({
       if (item.type !== "pdf") return false;
       const pdf = item.data as import("@/lib/workspace-state/types").PdfData;
       if (!pdf.fileUrl) return false;
-      if (pdf.ocrPages?.length) return false;
       if (pdf.ocrStatus === "processing" || pdf.ocrStatus === "complete") return false;
       if (migratedIdsRef.current.has(item.id)) return false;
       return true;
@@ -383,14 +380,11 @@ export default function WorkspaceContent({
     onDragStop();
   }, [onDragStop]);
 
-  // Check if we're in a filtered/folder view with no items
-  const isFiltering = searchQuery.trim() !== '' || activeFolderId !== null;
-  // Temporary filters (search) should not save layouts, but folder views should
-  const isTemporaryFilter = searchQuery.trim() !== '';
+  // Check if we're in folder view with no items
+  const isFiltering = activeFolderId !== null;
 
-  // Show empty state if no items exist at all OR if filtering yields no results (and no search query)
-  // This allows users to see the "Drag and Drop" prompt when selecting a new empty folder
-  if ((viewState.items ?? []).length === 0 || (isFiltering && !searchQuery && filteredItems.length === 0)) {
+  // Show empty state if no items exist at all OR if folder filtering yields no results
+  if ((viewState.items ?? []).length === 0 || (isFiltering && filteredItems.length === 0)) {
     return (
       <div className={showJsonView ? "h-full w-full" : "flex-1 py-4 overflow-hidden"}>
         <div className={`${selectedCardIdsArray.length > 0 ? 'pb-20' : ''} size-full workspace-grid-container px-4 sm:px-6`}>
@@ -455,24 +449,6 @@ export default function WorkspaceContent({
     );
   }
 
-  // Show no results message if search has no matches
-  if (searchQuery && filteredItems.length === 0) {
-    return (
-      <div className={showJsonView ? "h-full w-full" : "flex-1 py-4 overflow-hidden"}>
-        <div className={`${selectedCardIdsArray.length > 0 ? 'pb-20' : ''} size-full workspace-grid-container px-4 sm:px-6`}>
-          <EmptyState className="w-full min-w-0 max-w-full">
-            <div className="mx-auto max-w-lg text-center px-6 py-10">
-              <h2 className="text-lg font-semibold text-foreground">No results found</h2>
-              <p className="mt-2 text-sm text-muted-foreground">
-                {`No items match "${searchQuery}". Try a different search term.`}
-              </p>
-            </div>
-          </EmptyState>
-        </div>
-      </div>
-    );
-  }
-
   return (
     <div className={showJsonView ? "h-full w-full" : "py-4"}>
       {showJsonView ? (
@@ -520,11 +496,11 @@ export default function WorkspaceContent({
         </div>
       ) : (
         <WorkspaceGrid
-          key={searchQuery || activeFolderId ? 'filtered' : 'all'}
+          key={activeFolderId ?? 'root'}
           items={filteredItems}
           allItems={viewState.items}
           isFiltered={isFiltering}
-          isTemporaryFilter={isTemporaryFilter}
+          isTemporaryFilter={false}
           onDragStart={handleDragStart}
           onDragStop={handleDragStop}
           onUpdateItem={handleUpdateItem}
diff --git a/src/components/workspace-canvas/WorkspaceHeader.tsx b/src/components/workspace-canvas/WorkspaceHeader.tsx
index 2e881a74..94faae03 100644
--- a/src/components/workspace-canvas/WorkspaceHeader.tsx
+++ b/src/components/workspace-canvas/WorkspaceHeader.tsx
@@ -59,8 +59,7 @@ import { renderWorkspaceMenuItems } from "./workspace-menu-items";
 import { PromptBuilderDialog } from "@/components/assistant-ui/PromptBuilderDialog";
 interface WorkspaceHeaderProps {
   titleInputRef: React.RefObject<HTMLInputElement | null>;
-  searchQuery: string;
-  onSearchChange: (query: string) => void;
+  onOpenSearch?: () => void;
   // Save indicator props
   isSaving?: boolean;
   lastSavedAt?: Date | null;
@@ -110,8 +109,7 @@ interface WorkspaceHeaderProps {
 
 export function WorkspaceHeader({
   titleInputRef,
-  searchQuery,
-  onSearchChange,
+  onOpenSearch,
   isSaving,
   lastSavedAt,
   hasUnsavedChanges,
@@ -147,8 +145,6 @@ export function WorkspaceHeader({
   onUpdateActiveItem,
 }: WorkspaceHeaderProps) {
   const router = useRouter();
-  const [isFocused, setIsFocused] = useState(false);
-  const [isSearchExpanded, setIsSearchExpanded] = useState(false);
   const [isNewMenuOpen, setIsNewMenuOpen] = useState(false);
   const [showRenameDialog, setShowRenameDialog] = useState(false);
   const [renamingTarget, setRenamingTarget] = useState<{ id: string, type: 'folder' | 'item' } | null>(null);
@@ -162,7 +158,6 @@ export function WorkspaceHeader({
   const openAudioDialog = useAudioRecordingStore((s) => s.openDialog);
   const closeAudioDialog = useAudioRecordingStore((s) => s.closeDialog);
   const renameInputRef = useRef<HTMLInputElement>(null);
-  const searchInputRef = useRef<HTMLInputElement>(null);
   const pathname = usePathname();
   const isWorkspaceRoute = pathname.startsWith("/workspace");
 
@@ -238,13 +233,6 @@ export function WorkspaceHeader({
     }
   }, [showRenameDialog]);
 
-  // Auto-focus search input when expanded
-  useEffect(() => {
-    if (isSearchExpanded && searchInputRef.current) {
-      searchInputRef.current.focus();
-    }
-  }, [isSearchExpanded]);
-
   // Listen for drag hover events on breadcrumb elements
   useEffect(() => {
     const handleDragHover = (e: Event) => {
@@ -291,35 +279,6 @@ export function WorkspaceHeader({
     };
   }, []);
 
-  // Handle keyboard shortcut Cmd/Ctrl+K to expand search
-  useEffect(() => {
-    const handleKeyDown = (e: KeyboardEvent) => {
-      // Cmd+K / Ctrl+K - Expand and focus search
-      if ((e.metaKey || e.ctrlKey) && e.key === 'k') {
-        e.preventDefault();
-        setIsSearchExpanded(true);
-      }
-    };
-
-    window.addEventListener('keydown', handleKeyDown);
-    return () => {
-      window.removeEventListener('keydown', handleKeyDown);
-    };
-  }, []);
-
-  // Handle search input blur - collapse if empty
-  const handleSearchBlur = () => {
-    setIsFocused(false);
-    if (!searchQuery) {
-      setIsSearchExpanded(false);
-    }
-  };
-
-  // Handle search icon click
-  const handleSearchIconClick = () => {
-    setIsSearchExpanded(true);
-  };
-
   const handleYouTubeCreate = useCallback((url: string, name: string, thumbnail?: string) => {
     if (addItem) {
       addItem("youtube", name, { url, thumbnail });
@@ -906,71 +865,25 @@ export function WorkspaceHeader({
               </Tooltip>
             )}
 
-            {/* Search Input */}
-            {isSearchExpanded ? (
-              <div className="relative w-24" data-tour="search-bar">
-                <Search
-                  className={cn(
-                    "absolute left-2.5 top-1/2 -translate-y-1/2 h-4 w-4 transition-colors duration-200 pointer-events-none z-10",
-                    isFocused ? "text-sidebar-foreground" : "text-sidebar-foreground/70"
-                  )}
-                />
-                <input
-                  ref={(node) => {
-                    searchInputRef.current = node;
-                    if (titleInputRef) {
-                      (titleInputRef as React.MutableRefObject<HTMLInputElement | null>).current = node;
-                    }
-                  }}
-                  value={searchQuery}
-                  onChange={(e: React.ChangeEvent<HTMLInputElement>) => {
-                    onSearchChange(e.target.value);
-                  }}
-                  onFocus={() => setIsFocused(true)}
-                  onBlur={handleSearchBlur}
-                  placeholder="Search..."
+            {/* Search - opens command palette */}
+            <Tooltip>
+              <TooltipTrigger asChild>
+                <button
+                  onClick={() => onOpenSearch?.()}
                   className={cn(
-                    "w-full h-8 pl-9 outline-none rounded-md text-sm pointer-events-auto box-border",
-                    searchQuery ? "pr-8" : "pr-3",
-                    "border border-sidebar-border text-sidebar-foreground/70 placeholder:text-sidebar-foreground/50 transition-colors",
-                    isFocused
-                      ? "text-sidebar-foreground bg-accent"
-                      : "hover:text-sidebar-foreground hover:bg-accent"
+                    "h-8 w-8 flex items-center justify-center rounded-md transition-colors pointer-events-auto cursor-pointer",
+                    "border border-sidebar-border text-muted-foreground hover:text-sidebar-foreground hover:bg-accent"
                   )}
-                />
-                {/* Clear button - only show when there's text */}
-                {searchQuery && (
-                  <button
-                    onClick={() => {
-                      onSearchChange('');
-                    }}
-                    className="absolute right-2.5 top-1/2 -translate-y-1/2 h-4 w-4 text-sidebar-foreground/70 hover:text-sidebar-foreground hover:scale-110 transition-all duration-200 pointer-events-auto z-10 cursor-pointer"
-                    aria-label="Clear search"
-                  >
-                    <X className="h-4 w-4" />
-                  </button>
-                )}
-              </div>
-            ) : (
-              <Tooltip>
-                <TooltipTrigger asChild>
-                  <button
-                    onClick={handleSearchIconClick}
-                    className={cn(
-                      "h-8 w-8 flex items-center justify-center rounded-md transition-colors pointer-events-auto cursor-pointer",
-                      "border border-sidebar-border text-muted-foreground hover:text-sidebar-foreground hover:bg-accent"
-                    )}
-                    data-tour="search-bar"
-                    aria-label="Search workspace"
-                  >
-                    <Search className="h-4 w-4" />
-                  </button>
-                </TooltipTrigger>
-                <TooltipContent side="bottom">
-                  Search workspace <Kbd className="ml-1">{formatKeyboardShortcut('K')}</Kbd>
-                </TooltipContent>
-              </Tooltip>
-            )}
+                  data-tour="search-bar"
+                  aria-label="Search workspace"
+                >
+                  <Search className="h-4 w-4" />
+                </button>
+              </TooltipTrigger>
+              <TooltipContent side="bottom">
+                Search workspace <Kbd className="ml-1">{formatKeyboardShortcut('K')}</Kbd>
+              </TooltipContent>
+            </Tooltip>
 
             {/* New Button */}
             {addItem && (
diff --git a/src/components/workspace-canvas/WorkspaceSearchDialog.tsx b/src/components/workspace-canvas/WorkspaceSearchDialog.tsx
new file mode 100644
index 00000000..734d2fc3
--- /dev/null
+++ b/src/components/workspace-canvas/WorkspaceSearchDialog.tsx
@@ -0,0 +1,171 @@
+"use client";
+
+import { useState, useMemo, useEffect, useCallback } from "react";
+import { ChevronRight, FolderOpen } from "lucide-react";
+import {
+  CommandDialog,
+  CommandInput,
+  CommandList,
+  CommandEmpty,
+  CommandItem,
+} from "@/components/ui/command";
+import type { Item } from "@/lib/workspace-state/types";
+import {
+  rankWorkspaceSearchResults,
+  getFolderPath,
+} from "@/lib/workspace-state/search";
+import { getCardTypeIcon } from "@/components/chat/WorkspaceItemPicker";
+import { useUIStore } from "@/lib/stores/ui-store";
+
+interface WorkspaceSearchDialogProps {
+  open: boolean;
+  onOpenChange: (open: boolean) => void;
+  items: Item[];
+  currentWorkspaceId: string | null;
+  isLoadingWorkspace: boolean;
+}
+
+export function WorkspaceSearchDialog({
+  open,
+  onOpenChange,
+  items,
+  currentWorkspaceId,
+  isLoadingWorkspace,
+}: WorkspaceSearchDialogProps) {
+  const [query, setQuery] = useState("");
+  const navigateToFolder = useUIStore((state) => state.navigateToFolder);
+  const setActiveFolderId = useUIStore((state) => state.setActiveFolderId);
+  const setOpenModalItemId = useUIStore((state) => state.setOpenModalItemId);
+
+  const safeItems = items ?? [];
+
+  // Reset query when workspace changes
+  useEffect(() => {
+    if (!open) return;
+    setQuery("");
+  }, [currentWorkspaceId, open]);
+
+  const rankedResults = useMemo(
+    () => rankWorkspaceSearchResults(safeItems, query),
+    [safeItems, query]
+  );
+
+  const handleSelect = useCallback(
+    (item: Item) => {
+      // No-op if item not found (workspace switch / race)
+      const exists = safeItems.some((i) => i.id === item.id);
+      if (!exists) return;
+
+      onOpenChange(false);
+
+      if (item.type === "folder") {
+        navigateToFolder(item.id);
+      } else {
+        // Ensure breadcrumb shows the item's folder, then open the item
+        if (item.folderId) {
+          setActiveFolderId(item.folderId);
+        } else {
+          setActiveFolderId(null);
+        }
+        setOpenModalItemId(item.id);
+      }
+    },
+    [safeItems, onOpenChange, navigateToFolder, setActiveFolderId, setOpenModalItemId]
+  );
+
+  const getFolderPathItems = useCallback(
+    (item: Item): Item[] => {
+      if (!item.folderId) return [];
+      return getFolderPath(item.folderId, safeItems);
+    },
+    [safeItems]
+  );
+
+  const emptyMessage = useMemo(() => {
+    if (isLoadingWorkspace || !currentWorkspaceId) {
+      return "Loading...";
+    }
+    if (safeItems.length === 0) {
+      return "No items in this workspace.";
+    }
+    if (query.trim()) {
+      return `No results for "${query}".`;
+    }
+    return "Type to search...";
+  }, [isLoadingWorkspace, currentWorkspaceId, safeItems.length, query]);
+
+  return (
+    <CommandDialog
+      open={open}
+      onOpenChange={onOpenChange}
+      title="Search workspace"
+      description="Search for items and folders"
+      shouldFilter={false}
+    >
+      <CommandInput
+        placeholder="Search items..."
+        value={query}
+        onValueChange={setQuery}
+      />
+      <CommandList>
+        <CommandEmpty>{emptyMessage}</CommandEmpty>
+        {rankedResults.map(({ item, matchType, contentSnippet }) => {
+          const Icon = getCardTypeIcon(item.type);
+          const folderPathItems = getFolderPathItems(item);
+          const hasLocation = folderPathItems.length > 0;
+          const hasContentSnippet = matchType === "content" && contentSnippet?.match;
+
+          return (
+            <CommandItem
+              key={item.id}
+              value={item.id}
+              onSelect={() => handleSelect(item)}
+            >
+              {Icon}
+              <div className="flex min-w-0 flex-1 flex-col gap-0.5">
+                <span className="truncate">{item.name || "Untitled"}</span>
+                {/* Breadcrumb-style folder path (matches header breadcrumbs) */}
+                {hasLocation && (
+                  <div className="flex items-center gap-1 text-xs text-muted-foreground min-w-0 overflow-hidden">
+                    {folderPathItems.map((folder, idx) => (
+                      <span key={folder.id} className="flex items-center gap-1 shrink-0">
+                        {idx > 0 && (
+                          <ChevronRight className="h-3 w-3 shrink-0 text-muted-foreground/50" />
+                        )}
+                        <FolderOpen
+                          className="h-3 w-3 shrink-0"
+                          style={{ color: folder.color ?? undefined }}
+                        />
+                        <span className="truncate">{folder.name}</span>
+                      </span>
+                    ))}
+                  </div>
+                )}
+                {/* Content match snippet with bold matching text */}
+                {hasContentSnippet && contentSnippet && (
+                  <div className="text-xs text-muted-foreground line-clamp-2">
+                    {contentSnippet.before && (
+                      <span>{contentSnippet.before}</span>
+                    )}
+                    <span className="font-semibold text-foreground/90">
+                      {contentSnippet.match}
+                    </span>
+                    {contentSnippet.after && (
+                      <span>{contentSnippet.after}</span>
+                    )}
+                  </div>
+                )}
+                {/* Subtitle when no location or content snippet */}
+                {item.subtitle && !hasLocation && !hasContentSnippet && (
+                  <span className="truncate text-xs text-muted-foreground">
+                    {item.subtitle}
+                  </span>
+                )}
+              </div>
+            </CommandItem>
+          );
+        })}
+      </CommandList>
+    </CommandDialog>
+  );
+}
diff --git a/src/components/workspace-canvas/WorkspaceSection.tsx b/src/components/workspace-canvas/WorkspaceSection.tsx
index 49da378c..0f7ab0a1 100644
--- a/src/components/workspace-canvas/WorkspaceSection.tsx
+++ b/src/components/workspace-canvas/WorkspaceSection.tsx
@@ -71,8 +71,7 @@ interface WorkspaceSectionProps {
 
   // View state
   showJsonView: boolean;
-  searchQuery: string;
-  onSearchChange: (query: string) => void;
+  onOpenSearch?: () => void;
 
   // Save state
   isSaving: boolean;
@@ -144,8 +143,7 @@ export function WorkspaceSection({
   currentSlug,
   state,
   showJsonView,
-  searchQuery,
-  onSearchChange,
+  onOpenSearch,
   isSaving,
   lastSavedAt,
   hasUnsavedChanges,
@@ -696,7 +694,6 @@ export function WorkspaceSection({
                   deleteItem={deleteItem}
                   updateAllItems={updateAllItems}
                   getStatePreviewJSON={getStatePreviewJSON}
-                  searchQuery={searchQuery}
                   columns={columns}
                   setOpenModalItemId={setOpenModalItemId}
                   scrollContainerRef={scrollAreaRef}
diff --git a/src/contexts/HomeAttachmentsContext.tsx b/src/contexts/HomeAttachmentsContext.tsx
index 2d26c7b5..6666f5e4 100644
--- a/src/contexts/HomeAttachmentsContext.tsx
+++ b/src/contexts/HomeAttachmentsContext.tsx
@@ -12,6 +12,14 @@ import {
 } from "react";
 import { toast } from "sonner";
 import { filterPasswordProtectedPdfs } from "@/lib/uploads/pdf-validation";
+import {
+  isOfficeDocument,
+  isWordFile,
+  isExcelFile,
+  isPptxFile,
+} from "@/lib/uploads/office-document-validation";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
+import { emitPasswordProtectedPdf } from "@/components/modals/PasswordProtectedPdfDialog";
 import { uploadFileDirect } from "@/lib/uploads/client-upload";
 
 const MAX_TOTAL_FILE_BYTES = 50 * 1024 * 1024; // 50 MB
@@ -88,11 +96,24 @@ export function HomeAttachmentsProvider({ children }: { children: ReactNode }) {
   const addFiles = useCallback(async (newFiles: File[]) => {
     if (newFiles.length === 0) return;
 
-    const pdfFiles = newFiles.filter(
+    // Reject Office documents — show dialog, don't add
+    const officeWord = newFiles.filter(isWordFile).map((f) => f.name);
+    const officeExcel = newFiles.filter(isExcelFile).map((f) => f.name);
+    const officePowerpoint = newFiles.filter(isPptxFile).map((f) => f.name);
+    if (officeWord.length > 0 || officeExcel.length > 0 || officePowerpoint.length > 0) {
+      emitOfficeDocumentRejected({
+        word: officeWord.length ? officeWord : undefined,
+        excel: officeExcel.length ? officeExcel : undefined,
+        powerpoint: officePowerpoint.length ? officePowerpoint : undefined,
+      });
+    }
+    const withoutOffice = newFiles.filter((f) => !isOfficeDocument(f));
+
+    const pdfFiles = withoutOffice.filter(
       (f) =>
         f.type === "application/pdf" || f.name.toLowerCase().endsWith(".pdf")
     );
-    const nonPdfFiles = newFiles.filter(
+    const nonPdfFiles = withoutOffice.filter(
       (f) =>
         f.type !== "application/pdf" && !f.name.toLowerCase().endsWith(".pdf")
     );
@@ -100,9 +121,7 @@ export function HomeAttachmentsProvider({ children }: { children: ReactNode }) {
     const { valid: validPdfs, rejected: protectedNames } =
       await filterPasswordProtectedPdfs(pdfFiles);
     if (protectedNames.length > 0) {
-      toast.error(
-        `Password-protected PDFs cannot be uploaded: ${protectedNames.join(", ")}`
-      );
+      emitPasswordProtectedPdf(protectedNames);
     }
     const toAdd = [...validPdfs, ...nonPdfFiles];
     if (toAdd.length === 0) return;
diff --git a/src/contexts/WorkspaceContext.tsx b/src/contexts/WorkspaceContext.tsx
index e931906b..d54d8459 100644
--- a/src/contexts/WorkspaceContext.tsx
+++ b/src/contexts/WorkspaceContext.tsx
@@ -1,12 +1,11 @@
 "use client";
 
-import React, { createContext, useContext, useState, useCallback, useEffect, useMemo } from "react";
+import React, { createContext, useContext, useState, useCallback, useMemo } from "react";
 import { useRouter, usePathname, useSearchParams } from "next/navigation";
 import { toast } from "sonner";
 import { useQuery, useMutation, useQueryClient } from "@tanstack/react-query";
 import type { WorkspaceWithState } from "@/lib/workspace-state/types";
 import { useWorkspaceStore } from "@/lib/stores/workspace-store";
-import { useSession } from "@/lib/auth-client";
 
 /**
  * Simplified WorkspaceContext - ONLY manages workspace list
@@ -43,11 +42,8 @@ export function WorkspaceProvider({ children }: { children: React.ReactNode }) {
   const router = useRouter();
   const pathname = usePathname();
   const currentWorkspaceId = useWorkspaceStore((state) => state.currentWorkspaceId);
-  const { data: session } = useSession();
   const queryClient = useQueryClient();
 
-  const [isCreatingWelcomeWorkspace, setIsCreatingWelcomeWorkspace] = useState(false);
-
   // Derive current slug synchronously from pathname (no useEffect delay)
   const currentSlug = useMemo(() => {
     if (pathname.startsWith("/workspace/") && pathname !== "/workspace") {
@@ -128,38 +124,6 @@ export function WorkspaceProvider({ children }: { children: React.ReactNode }) {
     await queryClient.invalidateQueries({ queryKey: ['workspaces'] });
   }, [queryClient]);
 
-  // Create welcome workspace for anonymous users
-  const createWelcomeWorkspace = useCallback(async () => {
-    if (isCreatingWelcomeWorkspace) return;
-
-    setIsCreatingWelcomeWorkspace(true);
-    try {
-      console.log("Welcome workspace creation disabled");
-      // const response = await fetch("/api/guest/create-welcome-workspace", {
-      //   method: "POST",
-      // });
-
-      // if (response.ok) {
-      //   const data = await response.json();
-      //   // Reload workspaces to get the new one
-      //   await loadWorkspaces();
-      //   // Redirect to home (workspace is created but user goes to home)
-      //   router.push("/home");
-      // } else {
-      //   console.error("[WORKSPACE CONTEXT] Failed to create welcome workspace");
-      // }
-    } catch (error) {
-      console.error("[WORKSPACE CONTEXT] Error creating welcome workspace:", error);
-    } finally {
-      setIsCreatingWelcomeWorkspace(false);
-    }
-  }, [isCreatingWelcomeWorkspace, loadWorkspaces, router]);
-
-  // TanStack Query automatically fetches on mount, no need for manual trigger
-
-  // Note: Welcome workspace creation is now handled lazily in WorkspaceGrid
-  // This prevents jarring dashboard flash and provides better UX
-
   // Switch workspace
   const switchWorkspace = useCallback(
     (slug: string) => {
diff --git a/src/lib/ai/tools/__tests__/edit-item-tool.test.ts b/src/lib/ai/tools/__tests__/edit-item-tool.test.ts
index f6527f4b..2fcf04a5 100644
--- a/src/lib/ai/tools/__tests__/edit-item-tool.test.ts
+++ b/src/lib/ai/tools/__tests__/edit-item-tool.test.ts
@@ -106,6 +106,34 @@ describe("createEditItemTool", () => {
     expect(result.message).toMatch(/not editable/);
   });
 
+  it("allows PDF rename-only and rejects PDF content edits", async () => {
+    const pdfItem = { id: "pdf-1", type: "pdf", name: "Syllabus.pdf", data: { fileUrl: "x", filename: "Syllabus.pdf" } };
+    mockResolveItem.mockReturnValueOnce(pdfItem);
+    mockLoadStateForTool.mockResolvedValueOnce({ success: true, state: { items: [pdfItem] } });
+
+    const tool: any = createEditItemTool(ctx);
+    const contentEditResult = await tool.execute({ itemName: "Syllabus.pdf", oldString: "foo", newString: "bar" });
+    expect(contentEditResult.success).toBe(false);
+    expect(contentEditResult.message).toMatch(/rename only|can only be renamed/i);
+
+    mockResolveItem.mockReturnValueOnce(pdfItem);
+    mockLoadStateForTool.mockResolvedValueOnce({ success: true, state: { items: [pdfItem] } });
+    mockWorkspaceWorker.mockResolvedValueOnce({ success: true, itemId: "pdf-1", message: "Renamed PDF" });
+
+    const renameResult = await tool.execute({
+      itemName: "Syllabus.pdf",
+      oldString: "",
+      newString: "",
+      newName: "Course Syllabus.pdf",
+    });
+    expect(renameResult.success).toBe(true);
+    expect(renameResult.itemName).toBe("Course Syllabus.pdf");
+    expect(mockWorkspaceWorker).toHaveBeenLastCalledWith(
+      "edit",
+      expect.objectContaining({ itemId: "pdf-1", itemType: "pdf", newName: "Course Syllabus.pdf" })
+    );
+  });
+
   it("calls workspaceWorker edit and returns renamed itemName", async () => {
     const tool: any = createEditItemTool(ctx);
     const result = await tool.execute({
@@ -133,6 +161,30 @@ describe("createEditItemTool", () => {
     expect(result.itemName).toBe("Renamed Note");
   });
 
+  it("supports rename-only with oldString='' and newString=''", async () => {
+    const tool: any = createEditItemTool(ctx);
+    const result = await tool.execute({
+      itemName: "My Note",
+      oldString: "",
+      newString: "",
+      newName: "Renamed Note",
+    });
+
+    expect(mockWorkspaceWorker).toHaveBeenCalledWith(
+      "edit",
+      expect.objectContaining({
+        workspaceId: "ws-1",
+        itemId: "note-1",
+        itemType: "note",
+        oldString: "",
+        newString: "",
+        newName: "Renamed Note",
+      })
+    );
+    expect(result.success).toBe(true);
+    expect(result.itemName).toBe("Renamed Note");
+  });
+
   it("passes through worker failures", async () => {
     mockWorkspaceWorker.mockResolvedValueOnce({
       success: false,
diff --git a/src/lib/ai/tools/edit-item-tool.ts b/src/lib/ai/tools/edit-item-tool.ts
index 527172a4..5bbed279 100644
--- a/src/lib/ai/tools/edit-item-tool.ts
+++ b/src/lib/ai/tools/edit-item-tool.ts
@@ -6,22 +6,23 @@ import type { WorkspaceToolContext } from "./workspace-tools";
 import { loadStateForTool, resolveItem } from "./tool-utils";
 import { getVirtualPath } from "@/lib/utils/virtual-workspace-fs";
 
-const EDITABLE_TYPES = ["note", "flashcard", "quiz"] as const;
+const EDITABLE_TYPES = ["note", "flashcard", "quiz", "pdf"] as const;
 
 /**
- * Create the editItem tool - unified edit for notes, flashcards, and quizzes.
+ * Create the editItem tool - unified edit for notes, flashcards, quizzes, and PDFs.
  * Uses oldString/newString search-replace on raw content from readWorkspace.
+ * PDFs support RENAME ONLY: oldString='', newString='', newName='new name'.
  */
 export function createEditItemTool(ctx: WorkspaceToolContext) {
     return tool({
         description:
-            "Edit a note, flashcard deck, or quiz. You must use readWorkspace at least once before editing. QUIZZES: readWorkspace may show '--- Progress (read-only) ---' at the top. That block is READ-ONLY. Never include it in oldString or newString. Only edit the {\"questions\":[...]} JSON. FULL REWRITE: oldString='' and newString=entire new content (quizzes: only the JSON). TARGETED EDIT: oldString must match exactly. When copying from readWorkspace: strip the line number prefix (e.g. '1: ' → the part after the space is the content). For notes, content starts at line 1 — no header to skip. Match exact whitespace, indentation, newlines. Do NOT minify JSON. Edit FAILS if oldString not found or matches multiple times — add more context or use replaceAll.",
+            "Edit a note, flashcard deck, quiz, or PDF. You must use readWorkspace at least once before editing. PDFs: RENAME ONLY — pass oldString='', newString='', and newName='new name'. PDF content cannot be edited. RENAME ONLY (notes/flashcards/quizzes): same pattern to rename without editing content. QUIZZES: readWorkspace may show '--- Progress (read-only) ---' at the top. That block is READ-ONLY. Never include it in oldString or newString. Only edit the {\"questions\":[...]} JSON. FULL REWRITE: oldString='' and newString=entire new content (quizzes: only the JSON). TARGETED EDIT: oldString must match exactly. When copying from readWorkspace: strip the line number prefix (e.g. '1: ' → the part after the space is the content). For notes, content starts at line 1 — no header to skip. Match exact whitespace, indentation, newlines. Do NOT minify JSON. Edit FAILS if oldString not found or matches multiple times — add more context or use replaceAll.",
         inputSchema: zodSchema(
             z
                 .object({
                     itemName: z
                         .string()
-                        .describe("Name of the item to edit (note, flashcard deck, or quiz; matched by fuzzy search)"),
+                        .describe("Name of the item to edit (note, flashcard deck, quiz, or PDF; matched by fuzzy search)"),
                     oldString: z
                         .string()
                         .describe(
@@ -64,21 +65,22 @@ export function createEditItemTool(ctx: WorkspaceToolContext) {
                 };
             }
 
-            if (oldString === undefined || oldString === null) {
+            const isRenameOnly = Boolean(newName) && (oldString === undefined || oldString === null || oldString === "") && (newString === undefined || newString === null || newString === "");
+            if (!isRenameOnly && (oldString === undefined || oldString === null)) {
                 return {
                     success: false,
-                    message: "oldString is required. Use '' for full rewrite.",
+                    message: "oldString is required. Use '' for full rewrite, or for rename-only pass oldString='', newString='', and newName.",
                 };
             }
 
-            if (newString === undefined || newString === null) {
+            if (!isRenameOnly && (newString === undefined || newString === null)) {
                 return {
                     success: false,
-                    message: "newString is required.",
+                    message: "newString is required. For rename-only, pass oldString='', newString='', and newName.",
                 };
             }
 
-            if (oldString === newString) {
+            if (oldString === newString && !isRenameOnly) {
                 return {
                     success: false,
                     message: "No changes to apply: oldString and newString are identical.",
@@ -128,7 +130,14 @@ export function createEditItemTool(ctx: WorkspaceToolContext) {
                 if (!EDITABLE_TYPES.includes(matchedItem.type as (typeof EDITABLE_TYPES)[number])) {
                     return {
                         success: false,
-                        message: `Item "${matchedItem.name}" is not editable (type: ${matchedItem.type}). Only notes, flashcards, and quizzes can be edited.`,
+                        message: `Item "${matchedItem.name}" is not editable (type: ${matchedItem.type}). Only notes, flashcards, quizzes, and PDFs can be edited.`,
+                    };
+                }
+
+                if (matchedItem.type === "pdf" && !isRenameOnly) {
+                    return {
+                        success: false,
+                        message: "PDFs can only be renamed, not edited. Use oldString='', newString='', and newName='new name'.",
                     };
                 }
 
@@ -142,7 +151,7 @@ export function createEditItemTool(ctx: WorkspaceToolContext) {
                 const workerResult = await workspaceWorker("edit", {
                     workspaceId: ctx.workspaceId,
                     itemId: matchedItem.id,
-                    itemType: matchedItem.type as "note" | "flashcard" | "quiz",
+                    itemType: matchedItem.type as "note" | "flashcard" | "quiz" | "pdf",
                     itemName: matchedItem.name,
                     oldString,
                     newString,
diff --git a/src/lib/ai/tools/search-workspace.ts b/src/lib/ai/tools/search-workspace.ts
index 7907bde6..60f58b29 100644
--- a/src/lib/ai/tools/search-workspace.ts
+++ b/src/lib/ai/tools/search-workspace.ts
@@ -25,7 +25,7 @@ function buildRegex(pattern: string): RegExp {
 export function createSearchWorkspaceTool(ctx: WorkspaceToolContext) {
     return tool({
         description:
-            "Grep search across workspace (notes, flashcards, PDFs, quizzes, audio). Finds locations—use readWorkspace for full content. include: type filter (note, flashcard, pdf, quiz, audio). path: folder prefix or exact item path; for long items use exact path then readWorkspace(path, lineStart) on matches. Plain text or regex. Max 100 matches.",
+            "Grep search across workspace (notes, flashcards, PDFs, quizzes, audio). Searches both item titles and content—use readWorkspace for full content. include: type filter (note, flashcard, pdf, quiz, audio). path: folder prefix or exact item path; for long items use exact path then readWorkspace(path, lineStart) on matches. Plain text or regex. Max 100 matches.",
         inputSchema: zodSchema(
             z.object({
                 pattern: z.string().describe("Search pattern (plain text or regex)"),
diff --git a/src/lib/ai/tools/workspace-search-utils.ts b/src/lib/ai/tools/workspace-search-utils.ts
index aa2b27c6..69a9d6fa 100644
--- a/src/lib/ai/tools/workspace-search-utils.ts
+++ b/src/lib/ai/tools/workspace-search-utils.ts
@@ -9,16 +9,23 @@ import { type Block } from "@/components/editor/BlockNoteEditor";
 
 /**
  * Extract plain text from an item for searching (grep).
- * Returns empty string for types with no searchable content.
+ * Includes virtual path and item title as the first lines (so path-based names like "Summary- Lecture #1" match),
+ * then content. Returns empty string for types with no searchable content.
  */
 export function extractSearchableText(item: Item, items: Item[]): string {
+    const title = item.name?.trim() ?? "";
+    const virtualPath = getVirtualPath(item, items);
+    const header = [virtualPath, title].filter(Boolean).join("\n");
+    const withHeader = (content: string) =>
+        content ? (header ? `${header}\n${content}` : content) : header;
+
     switch (item.type) {
         case "note": {
             const data = item.data as NoteData;
             if (Array.isArray(data.blockContent) && data.blockContent.length > 0) {
-                return serializeBlockNote(data.blockContent as Block[]);
+                return withHeader(serializeBlockNote(data.blockContent as Block[]));
             }
-            return "";
+            return header;
         }
         case "flashcard": {
             const data = item.data as FlashcardData;
@@ -28,30 +35,32 @@ export function extractSearchableText(item: Item, items: Item[]): string {
                     : data.front || data.back
                         ? [{ id: "legacy", front: data.front ?? "", back: data.back ?? "", frontBlocks: data.frontBlocks, backBlocks: data.backBlocks }]
                         : [];
-            return cards
+            const content = cards
                 .map((c) => {
                     const front = c.frontBlocks ? serializeBlockNote(c.frontBlocks as Block[]) : c.front;
                     const back = c.backBlocks ? serializeBlockNote(c.backBlocks as Block[]) : c.back;
                     return `${front}\n${back}`;
                 })
                 .join("\n\n");
+            return withHeader(content);
         }
         case "pdf": {
             const data = item.data as PdfData;
-            if (data.ocrPages?.length) {
-                return data.ocrPages.map((p) => p.markdown).filter(Boolean).join("\n\n");
-            }
-            return data.textContent ?? "";
+            const content = data.ocrPages?.length
+                ? data.ocrPages.map((p) => p.markdown).filter(Boolean).join("\n\n")
+                : data.textContent ?? "";
+            return withHeader(content);
         }
         case "quiz": {
             const data = item.data as QuizData;
             const questions = data.questions ?? [];
-            return questions
+            const content = questions
                 .map(
                     (q) =>
                         `${q.questionText}\n${q.options?.join("\n") ?? ""}\n${q.explanation ?? ""}`
                 )
                 .join("\n\n");
+            return withHeader(content);
         }
         case "audio": {
             const data = item.data as AudioData;
@@ -64,14 +73,14 @@ export function extractSearchableText(item: Item, items: Item[]): string {
                         .join("\n")
                 );
             }
-            return parts.join("\n");
+            return withHeader(parts.join("\n"));
         }
         case "image":
         case "youtube":
         case "folder":
-            return item.name;
+            return header || item.name;
         default:
-            return "";
+            return header;
     }
 }
 
diff --git a/src/lib/ai/workers/__tests__/workspace-worker.edit.test.ts b/src/lib/ai/workers/__tests__/workspace-worker.edit.test.ts
index f45e889b..5c488262 100644
--- a/src/lib/ai/workers/__tests__/workspace-worker.edit.test.ts
+++ b/src/lib/ai/workers/__tests__/workspace-worker.edit.test.ts
@@ -268,6 +268,45 @@ describe("workspaceWorker edit end-to-end paths", () => {
     expect(result.message).toMatch(/Invalid JSON after edit/i);
   });
 
+  it("rename-only: updates note name without touching content", async () => {
+    const noteContent = "Original note content";
+    mockLoadWorkspaceState.mockResolvedValue({
+      items: [
+        {
+          id: "note-1",
+          type: "note",
+          name: "My Note",
+          subtitle: "",
+          data: { field1: noteContent, blockContent: [] },
+        },
+      ],
+      globalTitle: "",
+      workspaceId: "ws-1",
+    });
+
+    mockExecute
+      .mockResolvedValueOnce([{ version: 1 }]) // get_workspace_version
+      .mockResolvedValueOnce([{ result: "(2,f)" }]); // append_workspace_event
+
+    const result = await workspaceWorker("edit", {
+      workspaceId: "ws-1",
+      itemId: "note-1",
+      itemType: "note",
+      itemName: "My Note",
+      oldString: "",
+      newString: "",
+      newName: "Renamed Note",
+    });
+
+    expect(result.success).toBe(true);
+    expect(result.message).toMatch(/Updated note successfully/);
+    expect(mockMarkdownToBlocks).not.toHaveBeenCalled();
+    expect(mockCreateEvent).toHaveBeenCalled();
+    const eventPayload = mockCreateEvent.mock.calls[0][1] as { id: string; changes: Record<string, unknown> };
+    expect(eventPayload.id).toBe("note-1");
+    expect(eventPayload.changes).toEqual({ name: "Renamed Note" });
+  });
+
   it("fails with clear message when oldString is ambiguous", async () => {
     mockLoadWorkspaceState.mockResolvedValue({
       items: [
diff --git a/src/lib/ai/workers/workspace-worker.ts b/src/lib/ai/workers/workspace-worker.ts
index e9a30a3e..4aa0d840 100644
--- a/src/lib/ai/workers/workspace-worker.ts
+++ b/src/lib/ai/workers/workspace-worker.ts
@@ -980,7 +980,11 @@ export async function workspaceWorker(
                 if (!params.itemId || !params.itemType) {
                     throw new Error("Item ID and itemType required for edit");
                 }
-                if (params.oldString === undefined || params.newString === undefined) {
+                const isRenameOnly =
+                    params.newName &&
+                    (params.oldString === undefined || params.oldString === "") &&
+                    (params.newString === undefined || params.newString === "");
+                if (!isRenameOnly && (params.oldString === undefined || params.newString === undefined)) {
                     throw new Error("oldString and newString required for edit");
                 }
 
@@ -992,8 +996,8 @@ export async function workspaceWorker(
 
                 const rename = params.newName;
                 const replaceAll = !!params.replaceAll;
-                const oldStr = String(params.oldString);
-                const newStr = String(params.newString);
+                const oldStr = String(params.oldString ?? "");
+                const newStr = String(params.newString ?? "");
 
                 if (existingItem.type === "note") {
                     const changes: Partial<Item> = {};
@@ -1006,20 +1010,26 @@ export async function workspaceWorker(
 
                     let contentOld = "";
                     let contentNew = "";
-                    if (oldStr === "") {
+                    if (isRenameOnly) {
                         contentOld = "";
-                        contentNew = newStr;
+                        contentNew = "";
+                        // Skip content update - only apply rename via changes.name above
                     } else {
-                        contentOld = normalizeLineEndings(getNoteContentAsMarkdown(existingItem.data as NoteData));
-                        const normOld = normalizeLineEndings(oldStr);
-                        const normNew = normalizeLineEndings(newStr);
-                        contentNew = applyReplace(contentOld, normOld, normNew, replaceAll);
-                    }
-                    contentNew = fixLLMDoubleEscaping(contentNew);
-                    const blockContent = await markdownToBlocks(contentNew);
-                    changes.data = { field1: contentNew, blockContent } as NoteData;
-                    if (params.sources !== undefined) {
-                        (changes.data as NoteData).sources = params.sources;
+                        if (oldStr === "") {
+                            contentOld = "";
+                            contentNew = newStr;
+                        } else {
+                            contentOld = normalizeLineEndings(getNoteContentAsMarkdown(existingItem.data as NoteData));
+                            const normOld = normalizeLineEndings(oldStr);
+                            const normNew = normalizeLineEndings(newStr);
+                            contentNew = applyReplace(contentOld, normOld, normNew, replaceAll);
+                        }
+                        contentNew = fixLLMDoubleEscaping(contentNew);
+                        const blockContent = await markdownToBlocks(contentNew);
+                        changes.data = { field1: contentNew, blockContent } as NoteData;
+                        if (params.sources !== undefined) {
+                            (changes.data as NoteData).sources = params.sources;
+                        }
                     }
 
                     if (Object.keys(changes).length === 0) {
@@ -1081,12 +1091,14 @@ export async function workspaceWorker(
                         })),
                     };
                     let serialized = JSON.stringify(payload, null, 2);
-                    serialized = applyReplace(
-                        normalizeLineEndings(serialized),
-                        normalizeLineEndings(oldStr),
-                        normalizeLineEndings(newStr),
-                        replaceAll
-                    );
+                    if (!isRenameOnly) {
+                        serialized = applyReplace(
+                            normalizeLineEndings(serialized),
+                            normalizeLineEndings(oldStr),
+                            normalizeLineEndings(newStr),
+                            replaceAll
+                        );
+                    }
 
                     let parsed: { cards?: Array<{ id?: string; front?: string; back?: string }> };
                     try {
@@ -1157,12 +1169,14 @@ export async function workspaceWorker(
                     const questions = data.questions ?? [];
                     const payload = { questions };
                     let serialized = JSON.stringify(payload, null, 2);
-                    serialized = applyReplace(
-                        normalizeLineEndings(serialized),
-                        normalizeLineEndings(oldStr),
-                        normalizeLineEndings(newStr),
-                        replaceAll
-                    );
+                    if (!isRenameOnly) {
+                        serialized = applyReplace(
+                            normalizeLineEndings(serialized),
+                            normalizeLineEndings(oldStr),
+                            normalizeLineEndings(newStr),
+                            replaceAll
+                        );
+                    }
 
                     let parsed: { questions?: QuizQuestion[] };
                     try {
@@ -1237,6 +1251,41 @@ export async function workspaceWorker(
                     };
                 }
 
+                if (existingItem.type === "pdf") {
+                    if (!isRenameOnly || !rename) {
+                        return {
+                            success: false,
+                            message: "PDFs can only be renamed. Use oldString='', newString='', and newName='new name'.",
+                        };
+                    }
+                    if (hasDuplicateName(currentState.items, rename, "pdf", existingItem.folderId ?? null, params.itemId)) {
+                        return { success: false, message: `A PDF named "${rename}" already exists in this folder` };
+                    }
+                    const changes: Partial<Item> = { name: rename };
+                    const event = createEvent("ITEM_UPDATED", { id: params.itemId, changes, source: "agent", name: rename }, userId, userName);
+                    const currentVersionResult = await db.execute(sql`
+                        SELECT get_workspace_version(${params.workspaceId}::uuid) as version
+                    `);
+                    const baseVersion = currentVersionResult[0]?.version || 0;
+                    const eventResult = await db.execute(sql`
+                        SELECT append_workspace_event(
+                            ${params.workspaceId}::uuid, ${event.id}::text, ${event.type}::text,
+                            ${JSON.stringify(event.payload)}::jsonb, ${event.timestamp}::bigint, ${event.userId}::text,
+                            ${baseVersion}::integer, ${event.userName ?? null}::text
+                        ) as result
+                    `);
+                    if (!eventResult?.length) throw new Error("Failed to update PDF");
+                    const appendResult = parseAppendResult(eventResult[0].result);
+                    if (appendResult.conflict) throw new Error("Workspace was modified by another user, please try again");
+                    return {
+                        success: true,
+                        itemId: params.itemId,
+                        message: `Renamed PDF to "${rename}"`,
+                        event,
+                        version: appendResult.version,
+                    };
+                }
+
                 throw new Error(`Item type "${existingItem.type}" is not editable`);
             }
 
diff --git a/src/lib/attachments/supabase-attachment-adapter.ts b/src/lib/attachments/supabase-attachment-adapter.ts
index a2f22c65..658a4bdd 100644
--- a/src/lib/attachments/supabase-attachment-adapter.ts
+++ b/src/lib/attachments/supabase-attachment-adapter.ts
@@ -5,7 +5,14 @@ import type {
 } from "@assistant-ui/react";
 import { uploadFileDirect } from "@/lib/uploads/client-upload";
 import { isPasswordProtectedPdf } from "@/lib/uploads/pdf-validation";
+import {
+  isOfficeDocument,
+  isWordFile,
+  isExcelFile,
+  isPptxFile,
+} from "@/lib/uploads/office-document-validation";
 import { emitPasswordProtectedPdf } from "@/components/modals/PasswordProtectedPdfDialog";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
 import { useAttachmentUploadStore } from "@/lib/stores/attachment-upload-store";
 
 const getUploadStore = () => useAttachmentUploadStore.getState();
@@ -21,7 +28,7 @@ const MAX_FILE_SIZE_BYTES = 50 * 1024 * 1024; // 50MB to match server limit
  */
 export class SupabaseAttachmentAdapter implements AttachmentAdapter {
   accept =
-    "image/*,video/*,audio/*,.pdf,.doc,.docx,.ppt,.pptx,.xls,.xlsx,.txt,.md,.csv,.json,.mp3,.wav,.ogg,.aac,.flac,.aiff,.webm,.m4a";
+    "image/*,video/*,audio/*,.pdf,.txt,.md,.csv,.json,.mp3,.wav,.ogg,.aac,.flac,.aiff,.webm,.m4a";
 
   // Map of attachment ID → upload promise (started eagerly in add())
   private pendingUploads = new Map<string, Promise<string>>();
@@ -33,6 +40,18 @@ export class SupabaseAttachmentAdapter implements AttachmentAdapter {
       );
     }
 
+    // Reject Office documents — convert to PDF at ilovepdf.com
+    if (isOfficeDocument(file)) {
+      const word = isWordFile(file) ? [file.name] : undefined;
+      const excel = isExcelFile(file) ? [file.name] : undefined;
+      const powerpoint = isPptxFile(file) ? [file.name] : undefined;
+      emitOfficeDocumentRejected({ word, excel, powerpoint });
+      const format = word ? "Word" : excel ? "Excel" : "PowerPoint";
+      throw new Error(
+        `"${file.name}" is a ${format} file. ${format} files are not supported. Convert to PDF first.`
+      );
+    }
+
     // Reject password-protected PDFs
     if (await isPasswordProtectedPdf(file)) {
       emitPasswordProtectedPdf([file.name]);
diff --git a/src/lib/stores/ui-store.ts b/src/lib/stores/ui-store.ts
index 27ce0f5c..0b4f8ba2 100644
--- a/src/lib/stores/ui-store.ts
+++ b/src/lib/stores/ui-store.ts
@@ -29,7 +29,6 @@ interface UIState {
   showCreateWorkspaceModal: boolean;
   showSheetModal: boolean;
   showJsonView: boolean;
-  searchQuery: string;
 
   activeFolderId: string | null; // Active folder for filtering
   selectedModelId: string; // Selected AI model ID
@@ -89,7 +88,6 @@ interface UIState {
 
   // Actions - UI Preferences
   setShowJsonView: (show: boolean) => void;
-  setSearchQuery: (query: string) => void;
 
   setActiveFolderId: (folderId: string | null) => void;
   /** Atomic: close panels, clear folder, deselect panel cards. Use when panel is focused and user navigates back. */
@@ -160,7 +158,6 @@ const initialState = {
 
   // UI Preferences
   showJsonView: false,
-  searchQuery: '',
 
   activeFolderId: null,
   selectedModelId: 'gemini-3-flash-preview',
@@ -450,7 +447,6 @@ export const useUIStore = create<UIState>()(
 
         // UI Preferences actions
         setShowJsonView: (show) => set({ showJsonView: show }),
-        setSearchQuery: (query) => set({ searchQuery: query }),
 
         setSelectedModelId: (modelId) => set({ selectedModelId: modelId }),
 
@@ -641,7 +637,6 @@ export const selectSecondaryOpenModalItemId = (state: UIState) => state.openPane
 
 export const selectUIPreferences = (state: UIState) => ({
   showJsonView: state.showJsonView,
-  searchQuery: state.searchQuery,
 });
 
 export const selectTextSelectionState = (state: UIState) => ({
diff --git a/src/lib/uploads/client-upload.ts b/src/lib/uploads/client-upload.ts
index e87f4618..c4744a67 100644
--- a/src/lib/uploads/client-upload.ts
+++ b/src/lib/uploads/client-upload.ts
@@ -12,6 +12,13 @@
  */
 
 import { convertHeicToJpegIfNeeded } from "./convert-heic";
+import { isOfficeDocument } from "./office-document-validation";
+import {
+  isWordFile,
+  isExcelFile,
+  isPptxFile,
+} from "./office-document-validation";
+import { emitOfficeDocumentRejected } from "@/components/modals/OfficeDocumentRejectedDialog";
 
 const MAX_FILE_SIZE_BYTES = 200 * 1024 * 1024; // 200MB
 
@@ -57,6 +64,13 @@ export async function uploadFileDirect(
 
   if (!urlResponse.ok) {
     const errorData = await urlResponse.json().catch(() => ({}));
+    if (urlResponse.status === 400 && isOfficeDocument(file)) {
+      emitOfficeDocumentRejected({
+        word: isWordFile(file) ? [file.name] : undefined,
+        excel: isExcelFile(file) ? [file.name] : undefined,
+        powerpoint: isPptxFile(file) ? [file.name] : undefined,
+      });
+    }
     throw new Error(
       errorData.error || `Failed to get upload URL: ${urlResponse.statusText}`
     );
@@ -131,6 +145,13 @@ async function uploadViaApiRoute(file: File): Promise<UploadResult> {
 
   if (!response.ok) {
     const errorData = await response.json().catch(() => ({}));
+    if (response.status === 400 && isOfficeDocument(file)) {
+      emitOfficeDocumentRejected({
+        word: isWordFile(file) ? [file.name] : undefined,
+        excel: isExcelFile(file) ? [file.name] : undefined,
+        powerpoint: isPptxFile(file) ? [file.name] : undefined,
+      });
+    }
     throw new Error(
       errorData.error || `Upload failed: ${response.statusText}`
     );
diff --git a/src/lib/uploads/office-document-validation.ts b/src/lib/uploads/office-document-validation.ts
new file mode 100644
index 00000000..35e6064e
--- /dev/null
+++ b/src/lib/uploads/office-document-validation.ts
@@ -0,0 +1,121 @@
+/**
+ * Validation for Office documents (Word, Excel, PowerPoint).
+ * These are rejected — users can convert to PDF at iLovePDF.
+ */
+
+export const CONVERT_URLS = {
+  word: "https://www.ilovepdf.com/word_to_pdf",
+  excel: "https://www.ilovepdf.com/excel_to_pdf",
+  powerpoint: "https://www.ilovepdf.com/powerpoint_to_pdf",
+} as const;
+
+export type OfficeDocumentType = keyof typeof CONVERT_URLS;
+
+// Word: .doc, .docx
+const WORD_MIMES = [
+  "application/msword",
+  "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+];
+const WORD_EXTS = [".doc", ".docx"];
+
+// Excel: .xls, .xlsx
+const EXCEL_MIMES = [
+  "application/vnd.ms-excel",
+  "application/vnd.openxmlformats-officedocument.spreadsheetml.sheet",
+];
+const EXCEL_EXTS = [".xls", ".xlsx"];
+
+// PowerPoint: .ppt, .pptx
+const PPTX_MIMES = [
+  "application/vnd.ms-powerpoint",
+  "application/vnd.openxmlformats-officedocument.presentationml.presentation",
+];
+const PPTX_EXTS = [".ppt", ".pptx"];
+
+function checkFile(
+  file: File,
+  exts: string[],
+  mimes: string[]
+): boolean {
+  const n = file.name.toLowerCase();
+  return exts.some((e) => n.endsWith(e)) || mimes.includes(file.type || "");
+}
+
+function checkByName(filename: string, exts: string[]): boolean {
+  const n = filename.toLowerCase();
+  return exts.some((e) => n.endsWith(e));
+}
+
+function checkByMime(contentType: string, mimes: string[]): boolean {
+  return mimes.includes(contentType);
+}
+
+export function isWordFile(file: File): boolean {
+  return checkFile(file, WORD_EXTS, WORD_MIMES);
+}
+
+export function isExcelFile(file: File): boolean {
+  return checkFile(file, EXCEL_EXTS, EXCEL_MIMES);
+}
+
+export function isPptxFile(file: File): boolean {
+  return checkFile(file, PPTX_EXTS, PPTX_MIMES);
+}
+
+export function isOfficeDocument(file: File): boolean {
+  return isWordFile(file) || isExcelFile(file) || isPptxFile(file);
+}
+
+export function isWordByName(filename: string): boolean {
+  return checkByName(filename, WORD_EXTS);
+}
+
+export function isExcelByName(filename: string): boolean {
+  return checkByName(filename, EXCEL_EXTS);
+}
+
+export function isPptxByName(filename: string): boolean {
+  return checkByName(filename, PPTX_EXTS);
+}
+
+export function isWordByMime(contentType: string): boolean {
+  return checkByMime(contentType, WORD_MIMES);
+}
+
+export function isExcelByMime(contentType: string): boolean {
+  return checkByMime(contentType, EXCEL_MIMES);
+}
+
+export function isPptxByMime(contentType: string): boolean {
+  return checkByMime(contentType, PPTX_MIMES);
+}
+
+export function isOfficeDocumentByName(filename: string): boolean {
+  return isWordByName(filename) || isExcelByName(filename) || isPptxByName(filename);
+}
+
+export function isOfficeDocumentByMime(contentType: string): boolean {
+  return isWordByMime(contentType) || isExcelByMime(contentType) || isPptxByMime(contentType);
+}
+
+/** Get convert URL for a file, or null if not an office document */
+export function getOfficeDocumentConvertUrl(file: File): string | null {
+  if (isWordFile(file)) return CONVERT_URLS.word;
+  if (isExcelFile(file)) return CONVERT_URLS.excel;
+  if (isPptxFile(file)) return CONVERT_URLS.powerpoint;
+  return null;
+}
+
+/** Get convert URL from filename/contentType (for API routes) */
+export function getOfficeDocumentConvertUrlFromMeta(
+  filename: string,
+  contentType: string
+): string | null {
+  if (isWordByName(filename) || isWordByMime(contentType))
+    return CONVERT_URLS.word;
+  if (isExcelByName(filename) || isExcelByMime(contentType))
+    return CONVERT_URLS.excel;
+  if (isPptxByName(filename) || isPptxByMime(contentType))
+    return CONVERT_URLS.powerpoint;
+  return null;
+}
diff --git a/src/lib/workspace-state/search.ts b/src/lib/workspace-state/search.ts
index d4dd0083..42796388 100644
--- a/src/lib/workspace-state/search.ts
+++ b/src/lib/workspace-state/search.ts
@@ -267,3 +267,133 @@ export function filterItemIdsForFolderCreation(
   return itemIds.filter((id) => !idsToExclude.has(id));
 }
 
+export interface ContentMatchSnippet {
+  before: string;
+  match: string;
+  after: string;
+}
+
+export interface RankedSearchResult {
+  item: Item;
+  score: number;
+  matchType: string;
+  /** When matchType is "content", a snippet with the matching text and context */
+  contentSnippet?: ContentMatchSnippet | null;
+}
+
+const SCORE_EXACT_NAME = 1000;
+const SCORE_PREFIX_NAME = 800;
+const SCORE_TOKEN_NAME = 600;
+const SCORE_SUBSTRING_META = 400;
+const SCORE_CONTENT = 200;
+
+const SNIPPET_CONTEXT_CHARS = 40;
+
+/**
+ * Extracts a snippet from content text showing the matching query with surrounding context.
+ * Used for content-match results in the command palette.
+ */
+function getContentMatchSnippet(
+  contentText: string,
+  queryTerms: string[]
+): ContentMatchSnippet | null {
+  if (!contentText || queryTerms.length === 0) return null;
+
+  const contentLower = contentText.toLowerCase();
+  let bestStart = -1;
+  let bestEnd = -1;
+
+  // Find the first occurrence of the first query term
+  const firstTerm = queryTerms[0];
+  const idx = contentLower.indexOf(firstTerm);
+  if (idx === -1) return null;
+
+  bestStart = idx;
+  bestEnd = idx + firstTerm.length;
+
+  // Extend to include other query terms if they appear nearby (within ~80 chars)
+  for (let i = 1; i < queryTerms.length; i++) {
+    const term = queryTerms[i];
+    const termIdx = contentLower.indexOf(term, bestStart);
+    if (termIdx !== -1 && termIdx <= bestEnd + 60) {
+      bestEnd = Math.max(bestEnd, termIdx + term.length);
+    }
+  }
+
+  const beforeStart = Math.max(0, bestStart - SNIPPET_CONTEXT_CHARS);
+  const afterEnd = Math.min(contentText.length, bestEnd + SNIPPET_CONTEXT_CHARS);
+
+  const before = (beforeStart > 0 ? "…" : "") + contentText.slice(beforeStart, bestStart).trimStart();
+  const match = contentText.slice(bestStart, bestEnd);
+  const after = contentText.slice(bestEnd, afterEnd).trimEnd() + (afterEnd < contentText.length ? "…" : "");
+
+  return { before, match, after };
+}
+
+/**
+ * Ranks workspace items by search relevance for command palette.
+ * Name matches score higher than content matches.
+ */
+export function rankWorkspaceSearchResults(
+  items: Item[],
+  query: string
+): RankedSearchResult[] {
+  if (!Array.isArray(items) || items.length === 0) return [];
+  if (!query || !query.trim()) return [];
+
+  const normalizedQuery = query.toLowerCase().trim();
+  const queryTerms = normalizedQuery.split(/\s+/).filter((term) => term.length > 0);
+  if (queryTerms.length === 0) return [];
+
+  const results: RankedSearchResult[] = [];
+
+  for (const item of items) {
+    const nameLower = (item.name ?? "").toLowerCase().trim();
+    const subtitleLower = (item.subtitle ?? "").toLowerCase();
+    const typeLower = (item.type ?? "").toLowerCase();
+    const metaIndex = [nameLower, subtitleLower, typeLower].filter(Boolean).join(" ");
+    const contentText = getSearchableDataText(item).toLowerCase();
+
+    let score = 0;
+    let matchType = "";
+
+    // 1. Exact name match
+    if (nameLower === normalizedQuery) {
+      score = SCORE_EXACT_NAME;
+      matchType = "exact";
+    }
+    // 2. Prefix match on name
+    else if (nameLower.startsWith(normalizedQuery)) {
+      score = SCORE_PREFIX_NAME;
+      matchType = "prefix";
+    }
+    // 3. Token/word match on name (all query terms found in name)
+    else if (queryTerms.every((term) => nameLower.includes(term))) {
+      score = SCORE_TOKEN_NAME;
+      matchType = "token";
+    }
+    // 4. Substring on name + subtitle + type
+    else if (queryTerms.every((term) => metaIndex.includes(term))) {
+      score = SCORE_SUBSTRING_META;
+      matchType = "meta";
+    }
+    // 5. Content-text matches
+    else if (queryTerms.every((term) => contentText.includes(term))) {
+      score = SCORE_CONTENT;
+      matchType = "content";
+    }
+
+    if (score > 0) {
+      const rawContent = getSearchableDataText(item);
+      const contentSnippet =
+        matchType === "content" && rawContent
+          ? getContentMatchSnippet(rawContent, queryTerms)
+          : null;
+      results.push({ item, score, matchType, contentSnippet });
+    }
+  }
+
+  results.sort((a, b) => b.score - a.score);
+  return results.slice(0, 50);
+}
+