diff --git a/packages/core/src/services/chatRecordingService.test.ts b/packages/core/src/services/chatRecordingService.test.ts
index 504999a671..61ba3d32a3 100644
--- a/packages/core/src/services/chatRecordingService.test.ts
+++ b/packages/core/src/services/chatRecordingService.test.ts
@@ -745,4 +745,36 @@ describe('ChatRecordingService', () => {
       expect(result[1].functionResponse!.id).toBe(callId);
     });
   });
+
+  describe('ENOENT (missing directory) handling', () => {
+    it('should ensure directory exists before writing conversation file', () => {
+      chatRecordingService.initialize();
+
+      const mkdirSyncSpy = vi.spyOn(fs, 'mkdirSync');
+      const writeFileSyncSpy = vi.spyOn(fs, 'writeFileSync');
+
+      chatRecordingService.recordMessage({
+        type: 'user',
+        content: 'Hello after dir cleanup',
+        model: 'gemini-pro',
+      });
+
+      // mkdirSync should be called with the parent directory and recursive option
+      const conversationFile = chatRecordingService.getConversationFilePath()!;
+      expect(mkdirSyncSpy).toHaveBeenCalledWith(
+        path.dirname(conversationFile),
+        { recursive: true },
+      );
+
+      // mkdirSync should be called before writeFileSync
+      const mkdirCallOrder = mkdirSyncSpy.mock.invocationCallOrder;
+      const writeCallOrder = writeFileSyncSpy.mock.invocationCallOrder;
+      const lastMkdir = mkdirCallOrder[mkdirCallOrder.length - 1];
+      const lastWrite = writeCallOrder[writeCallOrder.length - 1];
+      expect(lastMkdir).toBeLessThan(lastWrite);
+
+      mkdirSyncSpy.mockRestore();
+      writeFileSyncSpy.mockRestore();
+    });
+  });
 });
diff --git a/packages/core/src/services/chatRecordingService.ts b/packages/core/src/services/chatRecordingService.ts
index bdce4f5f9e..0b94825353 100644
--- a/packages/core/src/services/chatRecordingService.ts
+++ b/packages/core/src/services/chatRecordingService.ts
@@ -455,6 +455,8 @@ export class ChatRecordingService {
         conversation.lastUpdated = new Date().toISOString();
         const newContent = JSON.stringify(conversation, null, 2);
         this.cachedLastConvData = newContent;
+        // Ensure directory exists before writing (handles cases where temp dir was cleaned)
+        fs.mkdirSync(path.dirname(this.conversationFile), { recursive: true });
         fs.writeFileSync(this.conversationFile, newContent);
       }
     } catch (error) {