diff --git a/blueprints/conversation/__init__.py b/blueprints/conversation/__init__.py
index 2ebc915..4175eff 100644
--- a/blueprints/conversation/__init__.py
+++ b/blueprints/conversation/__init__.py
@@ -123,22 +123,13 @@ async def upload_image():
 
     await s3_upload_image(processed_bytes, key, output_content_type)
 
-    return jsonify(
-        {
-            "image_key": key,
-            "image_url": f"/api/conversation/image/{key}",
-        }
-    )
+    return jsonify({"image_key": key})
 
 
 @conversation_blueprint.get("/image/<path:image_key>")
 @jwt_refresh_token_required
 async def serve_image(image_key: str):
-    try:
-        url = await s3_presigned_url(image_key)
-    except Exception:
-        return jsonify({"error": "Image not found"}), 404
-
+    url = await s3_presigned_url(image_key)
     return jsonify({"url": url})
 
 
diff --git a/raggr-frontend/src/api/conversationService.ts b/raggr-frontend/src/api/conversationService.ts
index 1135058..efd4b58 100644
--- a/raggr-frontend/src/api/conversationService.ts
+++ b/raggr-frontend/src/api/conversationService.ts
@@ -125,7 +125,7 @@ class ConversationService {
   async uploadImage(
     file: File,
     conversationId: string,
-  ): Promise<{ image_key: string; image_url: string }> {
+  ): Promise<{ image_key: string }> {
     const formData = new FormData();
     formData.append("file", file);
     formData.append("conversation_id", conversationId);
diff --git a/raggr-frontend/src/components/QuestionBubble.tsx b/raggr-frontend/src/components/QuestionBubble.tsx
index 081c726..a3678e4 100644
--- a/raggr-frontend/src/components/QuestionBubble.tsx
+++ b/raggr-frontend/src/components/QuestionBubble.tsx
@@ -9,10 +9,17 @@ type QuestionBubbleProps = {
 
 export const QuestionBubble = ({ text, image_key }: QuestionBubbleProps) => {
   const [imageUrl, setImageUrl] = useState<string | null>(null);
+  const [imageError, setImageError] = useState(false);
 
   useEffect(() => {
     if (!image_key) return;
-    conversationService.getPresignedImageUrl(image_key).then(setImageUrl).catch(() => {});
+    conversationService
+      .getPresignedImageUrl(image_key)
+      .then(setImageUrl)
+      .catch((err) => {
+        console.error("Failed to load image:", err);
+        setImageError(true);
+      });
   }, [image_key]);
 
   return (
@@ -25,6 +32,12 @@ export const QuestionBubble = ({ text, image_key }: QuestionBubbleProps) => {
           "shadow-sm shadow-leaf/10",
         )}
       >
+        {imageError && (
+          <div className="flex items-center gap-2 text-xs text-charcoal/50 bg-charcoal/5 rounded-xl px-3 py-2 mb-2">
+            <span>🖼️</span>
+            <span>Image failed to load</span>
+          </div>
+        )}
         {imageUrl && (
           <img
             src={imageUrl}