diff --git a/backend/src/agents/middlewares/uploads_middleware.py b/backend/src/agents/middlewares/uploads_middleware.py
index 152512c..04f7018 100644
--- a/backend/src/agents/middlewares/uploads_middleware.py
+++ b/backend/src/agents/middlewares/uploads_middleware.py
@@ -189,7 +189,20 @@ class UploadsMiddleware(AgentMiddleware[UploadsMiddlewareState]):
 
         # Create files message and prepend to the last human message content
         files_message = self._create_files_message(files)
-        original_content = last_message.content if isinstance(last_message.content, str) else ""
+        
+        # Extract original content - handle both string and list formats
+        original_content = ""
+        if isinstance(last_message.content, str):
+            original_content = last_message.content
+        elif isinstance(last_message.content, list):
+            # Content is a list of content blocks (e.g., [{"type": "text", "text": "..."}])
+            text_parts = []
+            for block in last_message.content:
+                if isinstance(block, dict) and block.get("type") == "text":
+                    text_parts.append(block.get("text", ""))
+            original_content = "\n".join(text_parts)
+        
+        logger.info(f"Original message content: {original_content[:100] if original_content else '(empty)'}")
         
         # Create new message with combined content
         updated_message = HumanMessage(
diff --git a/frontend/src/components/workspace/messages/message-list-item.tsx b/frontend/src/components/workspace/messages/message-list-item.tsx
index 9b6206d..5f41c6e 100644
--- a/frontend/src/components/workspace/messages/message-list-item.tsx
+++ b/frontend/src/components/workspace/messages/message-list-item.tsx
@@ -115,6 +115,86 @@ function MessageContent_({
 
   const { thread_id } = useParams<{ thread_id: string }>();
 
+  // For human messages with uploaded files, render files outside the bubble
+  if (isHuman && uploadedFiles.length > 0) {
+    return (
+      <div className={cn("ml-auto flex flex-col gap-2", className)}>
+        {/* Uploaded files outside the message bubble */}
+        <UploadedFilesList files={uploadedFiles} threadId={thread_id} />
+        
+        {/* Message content inside the bubble (only if there's text) */}
+        {cleanContent && (
+          <AIElementMessageContent className="w-fit">
+            <AIElementMessageResponse
+              remarkPlugins={[[remarkMath, { singleDollarTextMath: true }]]}
+              rehypePlugins={[...rehypePlugins, [rehypeKatex, { output: "html" }]]}
+              components={{
+                a: ({
+                  href,
+                  children,
+                }: React.AnchorHTMLAttributes<HTMLAnchorElement>) => {
+                  if (!href) {
+                    return <span>{children}</span>;
+                  }
+
+                  // Check if this link matches a citation
+                  const citation = citationMap.get(href);
+                  if (citation) {
+                    return (
+                      <CitationLink citation={citation} href={href}>
+                        {children}
+                      </CitationLink>
+                    );
+                  }
+
+                  // Regular external link
+                  return (
+                    <a
+                      href={href}
+                      target="_blank"
+                      rel="noopener noreferrer"
+                      className="text-primary underline underline-offset-2 hover:no-underline"
+                    >
+                      {children}
+                    </a>
+                  );
+                },
+                img: ({ src, alt }: React.ImgHTMLAttributes<HTMLImageElement>) => {
+                  if (!src) return null;
+                  if (typeof src !== "string") {
+                    return (
+                      <img
+                        className="max-w-full overflow-hidden rounded-lg"
+                        src={src}
+                        alt={alt}
+                      />
+                    );
+                  }
+                  let url = src;
+                  if (src.startsWith("/mnt/")) {
+                    url = resolveArtifactURL(src, thread_id);
+                  }
+                  return (
+                    <a href={url} target="_blank" rel="noopener noreferrer">
+                      <img
+                        className="max-w-full overflow-hidden rounded-lg"
+                        src={url}
+                        alt={alt}
+                      />
+                    </a>
+                  );
+                },
+              }}
+            >
+              {cleanContent}
+            </AIElementMessageResponse>
+          </AIElementMessageContent>
+        )}
+      </div>
+    );
+  }
+
+  // Default rendering for non-human messages or human messages without files
   return (
     <AIElementMessageContent className={className}>
       {/* Uploaded files for human messages - show first */}
@@ -287,7 +367,7 @@ function UploadedFileCard({
         href={imageUrl}
         target="_blank"
         rel="noopener noreferrer"
-        className="group relative block overflow-hidden rounded-lg border"
+        className="group relative block overflow-hidden rounded-lg border border-border/40"
       >
         <img
           src={imageUrl}
@@ -300,7 +380,7 @@ function UploadedFileCard({
 
   // For non-image files, show file card
   return (
-    <div className="bg-background flex min-w-[120px] max-w-[200px] flex-col gap-1 rounded-lg border p-3 shadow-sm">
+    <div className="bg-background flex min-w-[120px] max-w-[200px] flex-col gap-1 rounded-lg border border-border/40 p-3 shadow-sm">
       <div className="flex items-start gap-2">
         <FileIcon className="text-muted-foreground mt-0.5 size-4 shrink-0" />
         <span
diff --git a/frontend/src/core/threads/hooks.ts b/frontend/src/core/threads/hooks.ts
index b0dfca9..dc41d8b 100644
--- a/frontend/src/core/threads/hooks.ts
+++ b/frontend/src/core/threads/hooks.ts
@@ -73,6 +73,12 @@ export function useSubmitThread({
   const callback = useCallback(
     async (message: PromptInputMessage) => {
       const text = message.text.trim();
+      
+      console.log('[useSubmitThread] Submitting message:', { 
+        text, 
+        hasFiles: !!message.files?.length,
+        filesCount: message.files?.length || 0 
+      });
 
       // Upload files first if any
       if (message.files && message.files.length > 0) {