diff --git a/backend/src/handlers/fileHandler.ts b/backend/src/handlers/fileHandler.ts
index 204e901..b6a1261 100644
--- a/backend/src/handlers/fileHandler.ts
+++ b/backend/src/handlers/fileHandler.ts
@@ -440,7 +440,13 @@ const chatWithFileStream = async (req: AuthenticatedRequest, res: Response): Pro
             return;
         }
         if (fileRecord.extractionStatus !== 'done') {
-            res.status(409).json({ message: 'Not ready for chat yet.' });
+            const statusMsg = fileRecord.extractionStatus === 'failed'
+                ? 'Extraction failed for this file. Re-run extraction from the file menu.'
+                : 'This file is still being processed. It usually takes 30-60 seconds — try again in a moment.';
+            res.status(409).json({
+                message: statusMsg,
+                extraction_status: fileRecord.extractionStatus,
+            });
             return;
         }
 
diff --git a/backend/src/services/searchPipeline.ts b/backend/src/services/searchPipeline.ts
index 4e8f9b4..1cea4cf 100644
--- a/backend/src/services/searchPipeline.ts
+++ b/backend/src/services/searchPipeline.ts
@@ -478,11 +478,19 @@ export const runSearchPipeline = async (
         };
     });
 
-    results.sort((a, b) => b.score - a.score);
-    logger.info(`search: ${results.length} results for "${rawQuery}" (top score=${results[0]?.score.toFixed(4)})`);
+    // Drop nameless results. These come from file_ids that the parent fetch
+    // couldn't find a matching summary row for (race condition between delete
+    // and re-extract, or orphaned chunk rows). The UI can't render them and
+    // they'd crash on .split() / .localeCompare().
+    const cleaned = results.filter((r) => typeof r.filename === "string" && r.filename.length > 0);
+    cleaned.sort((a, b) => b.score - a.score);
+    if (cleaned.length < results.length) {
+        logger.warn(`search: dropped ${results.length - cleaned.length} orphan result(s) without filename`);
+    }
+    logger.info(`search: ${cleaned.length} results for "${rawQuery}" (top score=${cleaned[0]?.score.toFixed(4)})`);
 
     // Cap to a reasonable top-K — UI doesn't need 200 results.
-    return results.slice(0, 30);
+    return cleaned.slice(0, 30);
 };
 
 // ---------- 7. Optional LLM rerank for the top results ----------
diff --git a/smartdrive-frontend/src/components/FileChat.tsx b/smartdrive-frontend/src/components/FileChat.tsx
index 17b24b7..9020c8c 100644
--- a/smartdrive-frontend/src/components/FileChat.tsx
+++ b/smartdrive-frontend/src/components/FileChat.tsx
@@ -349,9 +349,34 @@ export function FileChat({ fileId, fileName, ready }: Props) {
             </div>
 
             {error && (
-                <div className="text-xs text-red-600/90 flex items-start gap-1.5">
-                    <IconAlertTriangle size={12} className="mt-0.5 shrink-0" /> {error}
-                </div>
+                (() => {
+                    const isNotReady = /still being processed|not ready/i.test(error);
+                    const isFailed = /extraction failed/i.test(error);
+                    const isPrivate = /private/i.test(error);
+                    const tone = isNotReady
+                        ? "border-amber-300/60 bg-amber-50/70 text-amber-900 dark:border-amber-500/30 dark:bg-amber-500/10 dark:text-amber-100"
+                        : isPrivate
+                            ? "border-emerald-300/60 bg-emerald-50/70 text-emerald-900 dark:border-emerald-500/30 dark:bg-emerald-500/10 dark:text-emerald-100"
+                            : "border-red-300/60 bg-red-50/70 text-red-900 dark:border-red-500/30 dark:bg-red-500/10 dark:text-red-100";
+                    return (
+                        <div className={`text-xs flex items-start gap-1.5 rounded-md border px-3 py-2 ${tone}`}>
+                            <IconAlertTriangle size={12} className="mt-0.5 shrink-0" />
+                            <div className="min-w-0">
+                                <div>{error}</div>
+                                {isNotReady && (
+                                    <div className="mt-1 opacity-80">
+                                        The file is being indexed in the background. This usually takes 30-60 seconds.
+                                    </div>
+                                )}
+                                {isFailed && (
+                                    <div className="mt-1 opacity-80">
+                                        Open the file menu and click &ldquo;Re-run extraction&rdquo; to try again.
+                                    </div>
+                                )}
+                            </div>
+                        </div>
+                    );
+                })()
             )}
 
             <div className="flex gap-2 items-end">
diff --git a/smartdrive-frontend/src/components/FileListWithDrawer.tsx b/smartdrive-frontend/src/components/FileListWithDrawer.tsx
index b350c8c..5c9a2f2 100644
--- a/smartdrive-frontend/src/components/FileListWithDrawer.tsx
+++ b/smartdrive-frontend/src/components/FileListWithDrawer.tsx
@@ -492,7 +492,7 @@ function FileCard({
                                 </div>
                             </div>
                             {(() => {
-                                const ext = file.filename.split(".").pop()?.toUpperCase();
+                                const ext = (file.filename ?? "").split(".").pop()?.toUpperCase();
                                 if (!ext || ext.length > 5) return null;
                                 return (
                                     <div className="text-[11px] font-semibold tracking-wider px-2 py-1 rounded-md bg-background/70 text-foreground/80 ring-1 ring-border">
@@ -697,8 +697,8 @@ function sortFiles(arr: UploadItem[], kind: SortKind): UploadItem[] {
     switch (kind) {
         case "newest": return copy.sort((a, b) => new Date(b.created_at).getTime() - new Date(a.created_at).getTime());
         case "oldest": return copy.sort((a, b) => new Date(a.created_at).getTime() - new Date(b.created_at).getTime());
-        case "name": return copy.sort((a, b) => a.filename.localeCompare(b.filename));
-        case "type": return copy.sort((a, b) => a.filetype.localeCompare(b.filetype));
+        case "name": return copy.sort((a, b) => (a.filename ?? "").localeCompare(b.filename ?? ""));
+        case "type": return copy.sort((a, b) => (a.filetype ?? "").localeCompare(b.filetype ?? ""));
         case "status": {
             const order: Record<string, number> = { failed: 0, processing: 1, pending: 2, done: 3 };
             return copy.sort((a, b) => (order[a.extraction_status ?? "done"] ?? 4) - (order[b.extraction_status ?? "done"] ?? 4));
@@ -805,7 +805,7 @@ export function FileListWithDrawer({
     const visibleFiles = useMemo(() => {
         const filtered = files.filter((f) => matchesFilter(f, filter));
         const searched = search.trim()
-            ? filtered.filter((f) => f.filename.toLowerCase().includes(search.toLowerCase().trim()))
+            ? filtered.filter((f) => (f.filename ?? "").toLowerCase().includes(search.toLowerCase().trim()))
             : filtered;
         return sortFiles(searched, sort);
     }, [files, filter, sort, search]);