diff --git a/client/src/components/Chat/Input/AskUserQuestionPopover.tsx b/client/src/components/Chat/Input/AskUserQuestionPopover.tsx
index 30125a9041..aeeaa8ac18 100644
--- a/client/src/components/Chat/Input/AskUserQuestionPopover.tsx
+++ b/client/src/components/Chat/Input/AskUserQuestionPopover.tsx
@@ -1,7 +1,7 @@
 import { memo } from 'react';
 import { useWatch } from 'react-hook-form';
 import { Button } from '@librechat/client';
-import { Check, ChevronDown, CornerDownLeft, X } from 'lucide-react';
+import { Check, ChevronDown, CornerDownLeft, TriangleAlert, X } from 'lucide-react';
 import useAskAnswerMode from '~/hooks/Input/useAskAnswerMode';
 import { useChatFormContext } from '~/Providers';
 import { useLocalize } from '~/hooks';
@@ -37,6 +37,7 @@ function AskUserQuestionPopoverContent({
     checked,
     multiSelect,
     locked,
+    errored,
     toggleChecked,
     canSubmit,
     submit,
@@ -112,6 +113,15 @@ function AskUserQuestionPopoverContent({
             </button>
           );
         })}
+        {/** A failed submission keeps the question answerable (controls stay
+         *   enabled), but the chat card that would show the error is hidden
+         *   while the popover is up — so surface it here for retry guidance. */}
+        {errored && (
+          <div className="flex items-center gap-1.5 px-2 pt-1 text-xs text-text-warning">
+            <TriangleAlert className="h-4 w-4 shrink-0" aria-hidden="true" />
+            {localize('com_ui_ask_answer_error')}
+          </div>
+        )}
         <div className="flex items-center justify-between gap-2 p-2">
           <button
             type="button"
diff --git a/client/src/hooks/Input/useAskAnswerMode.ts b/client/src/hooks/Input/useAskAnswerMode.ts
index 43aead74e8..c21127e7e4 100644
--- a/client/src/hooks/Input/useAskAnswerMode.ts
+++ b/client/src/hooks/Input/useAskAnswerMode.ts
@@ -371,6 +371,10 @@ export default function useAskAnswerMode(conversationId?: string | null) {
     submitAnswer,
     skip,
     handleComposerKeyDown,
+    /** The last submission failed but the question is still answerable — the
+     *  popover surfaces this so a composer/popover answer doesn't fail
+     *  silently (the chat card's error line is hidden while the popover is up). */
+    errored: status === 'error',
     /** Model-supplied "Other"-style label, folded into the inline input. */
     otherLabel,
     draftId,
diff --git a/client/src/locales/en/translation.json b/client/src/locales/en/translation.json
index 41e55c11cc..2747c88e71 100644
--- a/client/src/locales/en/translation.json
+++ b/client/src/locales/en/translation.json
@@ -857,6 +857,7 @@
   "com_ui_artifacts_options": "Artifacts Options",
   "com_ui_artifacts_subtext": "Lets the agent render React, HTML, SVG, Markdown, and Mermaid as interactive artifacts in a side panel instead of plain code blocks.",
   "com_ui_ascending": "Asc",
+  "com_ui_ask_answer_error": "Your answer couldn't be sent. Try again.",
   "com_ui_ask_type_below": "Or type your answer below",
   "com_ui_ask_type_below_only": "Type your answer below",
   "com_ui_ask_user": "Ask User",