diff --git a/src/components/message/MessagingPage.tsx b/src/components/message/MessagingPage.tsx
index dfbc1df..f24e916 100644
--- a/src/components/message/MessagingPage.tsx
+++ b/src/components/message/MessagingPage.tsx
@@ -348,19 +348,26 @@ export function MessagingPage({ initialConversationId }: { initialConversationId
 
   // Convert S3 keys to presigned download URLs for message attachments
   useEffect(() => {
+    const isS3Key = (val: string) => val && !val.startsWith('http://') && !val.startsWith('https://') && !val.startsWith('/') && !val.startsWith('data:');
+    const isUrl = (val: string) => val.startsWith('http://') || val.startsWith('https://');
+
     const convertFileUrls = async () => {
       for (const msg of messages) {
-        if ((msg.messageType === 'IMAGE' || msg.messageType === 'FILE') && msg.fileUrl) {
-          // Skip if already converted
-          if (messageFileUrls[msg.id]) continue;
-          // Skip if it's already an accessible URL (e.g., Giphy GIF URLs)
-          if (msg.fileUrl.startsWith('http://') || msg.fileUrl.startsWith('https://')) {
-            setMessageFileUrls(prev => ({ ...prev, [msg.id]: msg.fileUrl! }));
-            continue;
-          }
-          // Convert S3 key to presigned download URL
+        if (msg.messageType !== 'IMAGE' && msg.messageType !== 'FILE') continue;
+        if (messageFileUrls[msg.id]) continue;
+
+        // Determine the source: fileUrl or content (some messages store S3 key in content)
+        const source = msg.fileUrl || msg.content;
+        if (!source) continue;
+
+        if (isUrl(source)) {
+          setMessageFileUrls(prev => ({ ...prev, [msg.id]: source }));
+          continue;
+        }
+
+        if (isS3Key(source)) {
           try {
-            const presignedUrl = await uploadService.getPresignedDownloadUrl(msg.fileUrl);
+            const presignedUrl = await uploadService.getPresignedDownloadUrl(source);
             setMessageFileUrls(prev => ({ ...prev, [msg.id]: presignedUrl }));
           } catch {
             // Keep original if conversion fails
@@ -886,13 +893,31 @@ export function MessagingPage({ initialConversationId }: { initialConversationId
                               >
                                 {message.messageType === 'IMAGE' ? (
                                   messageFileUrls[message.id] ? (
-                                    <img
-                                      src={messageFileUrls[message.id]}
-                                      alt={message.fileName || 'Image'}
-                                      className="rounded-[12px] max-w-full cursor-pointer"
-                                      style={{ maxHeight: '250px' }}
-                                      onClick={() => window.open(messageFileUrls[message.id], '_blank')}
-                                    />
+                                    <>
+                                      <img
+                                        src={messageFileUrls[message.id]}
+                                        alt={message.fileName || 'Image'}
+                                        className="rounded-[12px] max-w-full cursor-pointer"
+                                        style={{ maxHeight: '250px' }}
+                                        onClick={() => window.open(messageFileUrls[message.id], '_blank')}
+                                        onError={(e) => {
+                                          const target = e.target as HTMLImageElement;
+                                          target.style.display = 'none';
+                                          const fallback = target.nextElementSibling;
+                                          if (fallback) (fallback as HTMLElement).style.display = 'flex';
+                                        }}
+                                      />
+                                      <div className="hidden items-center gap-2 px-3 py-2">
+                                        <Image src="/assets/icons/attachment-icon.svg" alt="Image" width={16} height={9} />
+                                        <span className="font-serif text-[13px]">{message.fileName || 'Image'}</span>
+                                        <button
+                                          onClick={() => window.open(messageFileUrls[message.id], '_blank')}
+                                          className="font-serif text-[12px] text-[#e58625] underline ml-1"
+                                        >
+                                          Download
+                                        </button>
+                                      </div>
+                                    </>
                                   ) : (
                                     <div className="w-[200px] h-[150px] rounded-[12px] overflow-hidden">
                                       <div className="w-full h-full shimmer-loading rounded-[12px]" />