diff --git a/frontend/src/components/thread/content/ThreadContent.tsx b/frontend/src/components/thread/content/ThreadContent.tsx
index 0b7a422d..6854c853 100644
--- a/frontend/src/components/thread/content/ThreadContent.tsx
+++ b/frontend/src/components/thread/content/ThreadContent.tsx
@@ -53,26 +53,52 @@ export function renderAttachments(attachments: string[], fileViewerHandler?: (fi
 // Render Markdown content while preserving XML tags that should be displayed as tool calls
 function preprocessTextOnlyTools(content: string): string {
     console.log('🔍 preprocessTextOnlyTools called with:', typeof content, content);
-    
+
     if (!content || typeof content !== 'string') {
         console.warn('❌ preprocessTextOnlyTools: Invalid content type:', typeof content, content);
         return content || '';
     }
-    
-    // Handle new function calls format for text-only tools - extract text parameter content
-    // Complete XML format
-    content = content.replace(/<function_calls>\s*<invoke name="ask">\s*<parameter name="text">([\s\S]*?)<\/parameter>[\s\S]*?<\/invoke>\s*<\/function_calls>/gi, '$1');
-    content = content.replace(/<function_calls>\s*<invoke name="complete">\s*<parameter name="text">([\s\S]*?)<\/parameter>[\s\S]*?<\/invoke>\s*<\/function_calls>/gi, '$1');
+
+    // For ask/complete tools, we need to preserve them if they have attachments
+    // Only strip them if they don't have attachments parameter
+
+    // Handle new function calls format - only strip if no attachments
+    content = content.replace(/<function_calls>\s*<invoke name="ask">\s*<parameter name="text">([\s\S]*?)<\/parameter>\s*<\/invoke>\s*<\/function_calls>/gi, (match) => {
+        if (match.includes('<parameter name="attachments"')) return match;
+        return match.replace(/<function_calls>\s*<invoke name="ask">\s*<parameter name="text">([\s\S]*?)<\/parameter>\s*<\/invoke>\s*<\/function_calls>/gi, '$1');
+    });
+
+    content = content.replace(/<function_calls>\s*<invoke name="complete">\s*<parameter name="text">([\s\S]*?)<\/parameter>\s*<\/invoke>\s*<\/function_calls>/gi, (match) => {
+        if (match.includes('<parameter name="attachments"')) return match;
+        return match.replace(/<function_calls>\s*<invoke name="complete">\s*<parameter name="text">([\s\S]*?)<\/parameter>\s*<\/invoke>\s*<\/function_calls>/gi, '$1');
+    });
+
     content = content.replace(/<function_calls>\s*<invoke name="present_presentation">[\s\S]*?<parameter name="text">([\s\S]*?)<\/parameter>[\s\S]*?<\/invoke>\s*<\/function_calls>/gi, '$1');
-    
-    // Handle streaming/partial XML for message tools - extract text parameter content even if incomplete
-    content = content.replace(/<function_calls>\s*<invoke name="ask">\s*<parameter name="text">([\s\S]*?)$/gi, '$1');
-    content = content.replace(/<function_calls>\s*<invoke name="complete">\s*<parameter name="text">([\s\S]*?)$/gi, '$1');
+
+    // Handle streaming/partial XML for message tools - only strip if no attachments visible yet
+    content = content.replace(/<function_calls>\s*<invoke name="ask">\s*<parameter name="text">([\s\S]*?)$/gi, (match) => {
+        if (match.includes('<parameter name="attachments"')) return match;
+        return match.replace(/<function_calls>\s*<invoke name="ask">\s*<parameter name="text">([\s\S]*?)$/gi, '$1');
+    });
+
+    content = content.replace(/<function_calls>\s*<invoke name="complete">\s*<parameter name="text">([\s\S]*?)$/gi, (match) => {
+        if (match.includes('<parameter name="attachments"')) return match;
+        return match.replace(/<function_calls>\s*<invoke name="complete">\s*<parameter name="text">([\s\S]*?)$/gi, '$1');
+    });
+
     content = content.replace(/<function_calls>\s*<invoke name="present_presentation">[\s\S]*?<parameter name="text">([\s\S]*?)$/gi, '$1');
-    
-    // Also handle old format for backward compatibility
-    content = content.replace(/<ask[^>]*>([\s\S]*?)<\/ask>/gi, '$1');
-    content = content.replace(/<complete[^>]*>([\s\S]*?)<\/complete>/gi, '$1');  
+
+    // Also handle old format - only strip if no attachments attribute
+    content = content.replace(/<ask[^>]*>([\s\S]*?)<\/ask>/gi, (match) => {
+        if (match.match(/<ask[^>]*attachments=/i)) return match;
+        return match.replace(/<ask[^>]*>([\s\S]*?)<\/ask>/gi, '$1');
+    });
+
+    content = content.replace(/<complete[^>]*>([\s\S]*?)<\/complete>/gi, (match) => {
+        if (match.match(/<complete[^>]*attachments=/i)) return match;
+        return match.replace(/<complete[^>]*>([\s\S]*?)<\/complete>/gi, '$1');
+    });
+
     content = content.replace(/<present_presentation[^>]*>([\s\S]*?)<\/present_presentation>/gi, '$1');
     return content;
 }
@@ -88,7 +114,7 @@ export function renderMarkdownContent(
 ) {
     // Preprocess content to convert text-only tools to natural text
     content = preprocessTextOnlyTools(content);
-    
+
     // If in debug mode, just display raw content in a pre tag
     if (debugMode) {
         return (
@@ -139,7 +165,7 @@ export function renderMarkdownContent(
                             {renderAttachments(attachmentArray, fileViewerHandler, sandboxId, project)}
                         </div>
                     );
-                    
+
                     // Also render standalone attachments outside the message
                     const standaloneAttachments = renderStandaloneAttachments(attachmentArray, fileViewerHandler, sandboxId, project);
                     if (standaloneAttachments) {
@@ -165,7 +191,7 @@ export function renderMarkdownContent(
                             {renderAttachments(attachmentArray, fileViewerHandler, sandboxId, project)}
                         </div>
                     );
-                    
+
                     // Also render standalone attachments outside the message
                     const standaloneAttachments = renderStandaloneAttachments(attachmentArray, fileViewerHandler, sandboxId, project);
                     if (standaloneAttachments) {
@@ -268,7 +294,7 @@ export function renderMarkdownContent(
                     {renderAttachments(attachments, fileViewerHandler, sandboxId, project)}
                 </div>
             );
-            
+
             // Also render standalone attachments outside the message
             const standaloneAttachments = renderStandaloneAttachments(attachments, fileViewerHandler, sandboxId, project);
             if (standaloneAttachments) {
@@ -296,7 +322,7 @@ export function renderMarkdownContent(
                     {renderAttachments(attachments, fileViewerHandler, sandboxId, project)}
                 </div>
             );
-            
+
             // Also render standalone attachments outside the message
             const standaloneAttachments = renderStandaloneAttachments(attachments, fileViewerHandler, sandboxId, project);
             if (standaloneAttachments) {
@@ -671,13 +697,13 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
                                 // Use merged groups instead of original grouped messages
                                 const finalGroupedMessages = mergedGroups;
 
-                                
+
                                 // Helper function to add streaming content to groups
                                 const appendStreamingContent = (content: string, isPlayback: boolean = false) => {
                                     const messageId = isPlayback ? 'playbackStreamingText' : 'streamingTextContent';
                                     const metadata = isPlayback ? 'playbackStreamingText' : 'streamingTextContent';
                                     const keySuffix = isPlayback ? 'playback-streaming' : 'streaming';
-                                    
+
                                     const lastGroup = finalGroupedMessages.at(-1);
                                     if (!lastGroup || lastGroup.type === 'user') {
                                         // Create new assistant group for streaming content
@@ -770,7 +796,7 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
                                             <div key={group.key} className="space-y-3">
                                                 {/* All file attachments rendered outside message bubble */}
                                                 {renderStandaloneAttachments(attachments as string[], handleOpenFileViewer, sandboxId, project, true)}
-                                                
+
                                                 <div className="flex justify-end">
                                                     <div className="flex max-w-[85%] rounded-3xl rounded-br-lg bg-card border px-4 py-3 break-words overflow-hidden">
                                                         <div className="space-y-3 min-w-0 flex-1">
@@ -789,7 +815,7 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
                                         // Get agent_id from the first assistant message in this group
                                         const firstAssistantMsg = group.messages.find(m => m.type === 'assistant');
                                         const groupAgentId = firstAssistantMsg?.agent_id;
-                                        
+
                                         return (
                                             <div key={group.key} ref={groupIndex === groupedMessages.length - 1 ? latestMessageRef : null}>
                                                 <div className="flex flex-col gap-2">
@@ -903,7 +929,7 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
 
                                                                         // Preprocess content first to remove text-only tool tags
                                                                         const textToRender = preprocessTextOnlyTools(streamingTextContent || '');
-                                                                        
+
                                                                         let detectedTag: string | null = null;
                                                                         let tagStartIndex = -1;
                                                                         if (textToRender) {
@@ -927,11 +953,11 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
                                                                         }
                                                                         const textBeforeTag = detectedTag ? textToRender.substring(0, tagStartIndex) : textToRender;
                                                                         const showCursor =
-                                                                          (streamHookStatus ===
-                                                                            'streaming' ||
-                                                                            streamHookStatus ===
-                                                                              'connecting') &&
-                                                                          !detectedTag;
+                                                                            (streamHookStatus ===
+                                                                                'streaming' ||
+                                                                                streamHookStatus ===
+                                                                                'connecting') &&
+                                                                            !detectedTag;
 
                                                                         // Show minimal processing indicator when agent is active but no streaming text after preprocessing
                                                                         if (!textToRender && (streamHookStatus === 'streaming' || streamHookStatus === 'connecting')) {
@@ -946,8 +972,8 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
 
                                                                         return (
                                                                             <>
-                                                                                <StreamingText 
-                                                                                    content={textBeforeTag} 
+                                                                                <StreamingText
+                                                                                    content={textBeforeTag}
                                                                                     className="text-sm prose prose-sm dark:prose-invert chat-markdown max-w-none [&>:first-child]:mt-0 prose-headings:mt-3 break-words overflow-wrap-anywhere"
                                                                                 />
 
@@ -972,7 +998,7 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
                                                                     {(() => {
                                                                         // Preprocess content first to remove text-only tool tags
                                                                         const textToRender = preprocessTextOnlyTools(streamingText || '');
-                                                                        
+
                                                                         let detectedTag: string | null = null;
                                                                         let tagStartIndex = -1;
                                                                         if (textToRender) {
@@ -1009,8 +1035,8 @@ export const ThreadContent: React.FC<ThreadContentProps> = ({
                                                                                     </pre>
                                                                                 ) : (
                                                                                     <>
-                                                                                        <StreamingText 
-                                                                                            content={textBeforeTag} 
+                                                                                        <StreamingText
+                                                                                            content={textBeforeTag}
                                                                                             className="text-sm prose prose-sm dark:prose-invert chat-markdown max-w-none [&>:first-child]:mt-0 prose-headings:mt-3 break-words overflow-wrap-anywhere"
                                                                                         />