fix(plan): clean up session directories and plans on deletion (#20914)

packages/cli/src/utils/sessionCleanup.test.ts

@@ -919,6 +919,32 @@ describe('Session Cleanup', () => {
         ),
       );
     });
+
+    it('should delete the session-specific directory', async () => {
+      const config = createMockConfig();
+      const settings: Settings = {
+        general: {
+          sessionRetention: {
+            enabled: true,
+            maxAge: '1d', // Very short retention to trigger deletion of all but current
+          },
+        },
+      };
+
+      // Mock successful file operations
+      mockFs.access.mockResolvedValue(undefined);
+      mockFs.unlink.mockResolvedValue(undefined);
+      mockFs.rm.mockResolvedValue(undefined);
+
+      await cleanupExpiredSessions(config, settings);
+
+      // Verify that fs.rm was called with the session directory for the deleted session that has sessionInfo
+      // recent456 should be deleted and its directory removed
+      expect(mockFs.rm).toHaveBeenCalledWith(
+        path.join('/tmp/test-project', 'recent456'),
+        expect.objectContaining({ recursive: true, force: true }),
+      );
+    });
   });
 
   describe('parseRetentionPeriod format validation', () => {

packages/cli/src/utils/sessionCleanup.ts

@@ -115,6 +115,17 @@ export async function cleanupExpiredSessions(
           } catch {
             /* ignore if doesn't exist */
           }
+
+          // ALSO cleanup the session-specific directory (contains plans, tasks, etc.)
+          const sessionDir = path.join(
+            config.storage.getProjectTempDir(),
+            sessionId,
+          );
+          try {
+            await fs.rm(sessionDir, { recursive: true, force: true });
+          } catch {
+            /* ignore if doesn't exist */
+          }
         }
 
         if (config.getDebugMode()) {

packages/core/src/services/chatRecordingService.test.ts

@@ -309,23 +309,33 @@ describe('ChatRecordingService', () => {
   });
 
   describe('deleteSession', () => {
-    it('should delete the session file and tool outputs if they exist', () => {
+    it('should delete the session file, tool outputs, session directory, and logs if they exist', () => {
+      const sessionId = 'test-session-id';
       const chatsDir = path.join(testTempDir, 'chats');
+      const logsDir = path.join(testTempDir, 'logs');
+      const toolOutputsDir = path.join(testTempDir, 'tool-outputs');
+      const sessionDir = path.join(testTempDir, sessionId);
+
       fs.mkdirSync(chatsDir, { recursive: true });
-      const sessionFile = path.join(chatsDir, 'test-session-id.json');
+      fs.mkdirSync(logsDir, { recursive: true });
+      fs.mkdirSync(toolOutputsDir, { recursive: true });
+      fs.mkdirSync(sessionDir, { recursive: true });
+
+      const sessionFile = path.join(chatsDir, `${sessionId}.json`);
       fs.writeFileSync(sessionFile, '{}');
 
-      const toolOutputDir = path.join(
-        testTempDir,
-        'tool-outputs',
-        'session-test-session-id',
-      );
+      const logFile = path.join(logsDir, `session-${sessionId}.jsonl`);
+      fs.writeFileSync(logFile, '{}');
+
+      const toolOutputDir = path.join(toolOutputsDir, `session-${sessionId}`);
       fs.mkdirSync(toolOutputDir, { recursive: true });
 
-      chatRecordingService.deleteSession('test-session-id');
+      chatRecordingService.deleteSession(sessionId);
 
       expect(fs.existsSync(sessionFile)).toBe(false);
+      expect(fs.existsSync(logFile)).toBe(false);
       expect(fs.existsSync(toolOutputDir)).toBe(false);
+      expect(fs.existsSync(sessionDir)).toBe(false);
     });
 
     it('should not throw if session file does not exist', () => {

packages/core/src/services/chatRecordingService.ts

@@ -569,6 +569,13 @@ export class ChatRecordingService {
         fs.unlinkSync(sessionPath);
       }
 
+      // Cleanup Activity logs in the project logs directory
+      const logsDir = path.join(tempDir, 'logs');
+      const logPath = path.join(logsDir, `session-${sessionId}.jsonl`);
+      if (fs.existsSync(logPath)) {
+        fs.unlinkSync(logPath);
+      }
+
       // Cleanup tool outputs for this session
       const safeSessionId = sanitizeFilenamePart(sessionId);
       const toolOutputDir = path.join(
@@ -585,6 +592,13 @@ export class ChatRecordingService {
       ) {
         fs.rmSync(toolOutputDir, { recursive: true, force: true });
       }
+
+      // ALSO cleanup the session-specific directory (contains plans, tasks, etc.)
+      const sessionDir = path.join(tempDir, safeSessionId);
+      // Robustness: Ensure the path is strictly within the temp root
+      if (fs.existsSync(sessionDir) && sessionDir.startsWith(tempDir)) {
+        fs.rmSync(sessionDir, { recursive: true, force: true });
+      }
     } catch (error) {
       debugLogger.error('Error deleting session file.', error);
       throw error;