diff --git a/frontend/src/components/ChatInterface.tsx b/frontend/src/components/ChatInterface.tsx
index 2cb0a22..eb33eed 100644
--- a/frontend/src/components/ChatInterface.tsx
+++ b/frontend/src/components/ChatInterface.tsx
@@ -68,18 +68,10 @@ const ChatInterface: React.FC = () => {
 
   const cleanMarkdown = (text: string): string => {
     return text
-      // Collapse all 2+ blank lines into single blank line everywhere
-      .replace(/\n{3,}/g, '\n\n')
-      // Remove blank line between heading and any content
-      .replace(/(^#{1,6}\s+.+)\n\n(?=\S)/gm, '$1\n')
-      // Remove blank line between bold header (**Text:**) and next line
-      .replace(/(\*\*[^*]+\*\*:?[^\n]*)\n\n(?=\S)/gm, '$1\n')
-      // Remove blank line before list items (after any text)
-      .replace(/([^\n])\n\n(?=\d+[\.\)]\s)/g, '$1\n')
-      .replace(/([^\n])\n\n(?=[-*]\s)/g, '$1\n')
-      // Remove blank lines between list items
-      .replace(/([-*]\s+[^\n]+)\n\n(?=[-*]\s)/g, '$1\n')
-      .replace(/(\d+[\.\)]\s+[^\n]+)\n\n(?=\d+[\.\)]\s)/g, '$1\n');
+      // Nuclear: collapse ALL double+ newlines to single newline
+      .replace(/\n{2,}/g, '\n')
+      // Add back paragraph break ONLY before bold section headers (**Text:**)
+      .replace(/\n(\*\*[^*]+\*\*)/g, '\n\n$1');
   };
 
   const handleSend = async () => {
diff --git a/frontend/src/context/ChatContext.tsx b/frontend/src/context/ChatContext.tsx
index 12eec4a..bdc4274 100644
--- a/frontend/src/context/ChatContext.tsx
+++ b/frontend/src/context/ChatContext.tsx
@@ -141,11 +141,32 @@ export const ChatProvider: React.FC<{ children: ReactNode }> = ({ children }) =>
           },
         ]);
 
-        // Update conversation in list (move to top)
-        setConversations((prev) => {
-          const updated = prev.filter((c) => c.id !== currentConversation.id);
-          return [currentConversation, ...updated];
-        });
+        // Auto-rename conversation on first message
+        if (currentConversation.title === 'New Conversation' && messages.length === 0) {
+          const autoTitle = content.length > 50
+            ? content.substring(0, 50).trim() + '...'
+            : content;
+          try {
+            await conversationAPI.update(currentConversation.id, autoTitle);
+            setCurrentConversation((prev) => prev ? { ...prev, title: autoTitle } : null);
+            setConversations((prev) => {
+              const updated = prev.filter((c) => c.id !== currentConversation.id);
+              return [{ ...currentConversation, title: autoTitle }, ...updated];
+            });
+          } catch {
+            // Rename failed — not critical, keep default title
+            setConversations((prev) => {
+              const updated = prev.filter((c) => c.id !== currentConversation.id);
+              return [currentConversation, ...updated];
+            });
+          }
+        } else {
+          // Update conversation in list (move to top)
+          setConversations((prev) => {
+            const updated = prev.filter((c) => c.id !== currentConversation.id);
+            return [currentConversation, ...updated];
+          });
+        }
       } catch (err: any) {
         console.error('Failed to send message:', err);
         setError(err.response?.data?.detail || 'Failed to send message');