diff --git a/blueprints/conversation/__init__.py b/blueprints/conversation/__init__.py
index d19ace2..4175eff 100644
--- a/blueprints/conversation/__init__.py
+++ b/blueprints/conversation/__init__.py
@@ -3,7 +3,7 @@ import json
 import logging
 import uuid
 
-from quart import Blueprint, Response, jsonify, make_response, request
+from quart import Blueprint, jsonify, make_response, request
 from quart_jwt_extended import (
     get_jwt_identity,
     jwt_refresh_token_required,
@@ -12,6 +12,7 @@ from quart_jwt_extended import (
 import blueprints.users.models
 from utils.image_process import analyze_user_image
 from utils.image_upload import ImageValidationError, process_image
+from utils.s3_client import generate_presigned_url as s3_presigned_url
 from utils.s3_client import get_image as s3_get_image
 from utils.s3_client import upload_image as s3_upload_image
 
@@ -122,27 +123,14 @@ 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:
-        image_bytes, content_type = await s3_get_image(image_key)
-    except Exception:
-        return jsonify({"error": "Image not found"}), 404
-
-    return Response(
-        image_bytes,
-        content_type=content_type,
-        headers={"Cache-Control": "private, max-age=3600"},
-    )
+    url = await s3_presigned_url(image_key)
+    return jsonify({"url": url})
 
 
 @conversation_blueprint.post("/stream-query")
diff --git a/raggr-frontend/src/api/conversationService.ts b/raggr-frontend/src/api/conversationService.ts
index 788089e..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);
@@ -147,8 +147,15 @@ class ConversationService {
     return await response.json();
   }
 
-  getImageUrl(imageKey: string): string {
-    return `/api/conversation/image/${imageKey}`;
+  async getPresignedImageUrl(imageKey: string): Promise<string> {
+    const response = await userService.fetchWithRefreshToken(
+      `${this.conversationBaseUrl}/image/${imageKey}`,
+    );
+    if (!response.ok) {
+      throw new Error("Failed to get image URL");
+    }
+    const data = await response.json();
+    return data.url;
   }
 
   async streamQuery(
diff --git a/raggr-frontend/src/components/QuestionBubble.tsx b/raggr-frontend/src/components/QuestionBubble.tsx
index b131c11..a3678e4 100644
--- a/raggr-frontend/src/components/QuestionBubble.tsx
+++ b/raggr-frontend/src/components/QuestionBubble.tsx
@@ -1,3 +1,4 @@
+import { useEffect, useState } from "react";
 import { cn } from "../lib/utils";
 import { conversationService } from "../api/conversationService";
 
@@ -7,6 +8,20 @@ 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((err) => {
+        console.error("Failed to load image:", err);
+        setImageError(true);
+      });
+  }, [image_key]);
+
   return (
     <div className="flex justify-end message-enter">
       <div
@@ -17,9 +32,15 @@ export const QuestionBubble = ({ text, image_key }: QuestionBubbleProps) => {
           "shadow-sm shadow-leaf/10",
         )}
       >
-        {image_key && (
+        {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={conversationService.getImageUrl(image_key)}
+            src={imageUrl}
             alt="Uploaded image"
             className="max-w-full rounded-xl mb-2"
           />
diff --git a/utils/s3_client.py b/utils/s3_client.py
index 443ef82..4d941a5 100644
--- a/utils/s3_client.py
+++ b/utils/s3_client.py
@@ -47,6 +47,16 @@ async def get_image(key: str) -> tuple[bytes, str]:
     return body, content_type
 
 
+async def generate_presigned_url(key: str, expires_in: int = 3600) -> str:
+    async with _get_client() as client:
+        url = await client.generate_presigned_url(
+            "get_object",
+            Params={"Bucket": S3_BUCKET_NAME, "Key": key},
+            ExpiresIn=expires_in,
+        )
+    return url
+
+
 async def delete_image(key: str) -> None:
     async with _get_client() as client:
         await client.delete_object(Bucket=S3_BUCKET_NAME, Key=key)