diff --git a/packages/extension-core/src/extension/session-manager.ts b/packages/extension-core/src/extension/session-manager.ts
index 9d51a7c..da3b6bf 100644
--- a/packages/extension-core/src/extension/session-manager.ts
+++ b/packages/extension-core/src/extension/session-manager.ts
@@ -186,9 +186,15 @@ export class SessionManager {
    * Get all sessions for a specific workflow file
    */
   getSessionsForWorkflow(workflowFile: string): SessionData[] {
+    // Most recent first; between equal times (created or restored in the same
+    // millisecond), the one added later.
     return Array.from(this.sessions.values())
-      .filter((s) => s.workflowFile === workflowFile)
-      .sort((a, b) => b.updatedAt - a.updatedAt);
+      .map((session, order) => ({ session, order }))
+      .filter(({ session }) => session.workflowFile === workflowFile)
+      .sort((a, b) => b.session.updatedAt - a.session.updatedAt
+        || b.session.createdAt - a.session.createdAt
+        || b.order - a.order)
+      .map(({ session }) => session);
   }
 
   /**
diff --git a/packages/extension-core/test/session-manager.test.ts b/packages/extension-core/test/session-manager.test.ts
index 8ee541b..7f4de88 100644
--- a/packages/extension-core/test/session-manager.test.ts
+++ b/packages/extension-core/test/session-manager.test.ts
@@ -247,17 +247,40 @@ describe('SessionManager', () => {
 
   describe('getSessionsForWorkflow', () => {
     it('should return sessions for specific workflow', async () => {
-      await sessionManager.createSession('/test/workflow1.py', 'Session 1');
-      mockACPClient.createSession.mockResolvedValue('session-2');
-      await sessionManager.createSession('/test/workflow2.py', 'Session 2');
-      mockACPClient.createSession.mockResolvedValue('session-3');
-      await sessionManager.createSession('/test/workflow1.py', 'Session 3');
+      // Each session at its own time, so the order is the updatedAt sort's.
+      vi.useFakeTimers({ toFake: ['Date'] });
+      try {
+        vi.setSystemTime(1_000);
+        await sessionManager.createSession('/test/workflow1.py', 'Session 1');
+        vi.setSystemTime(2_000);
+        mockACPClient.createSession.mockResolvedValue('session-2');
+        await sessionManager.createSession('/test/workflow2.py', 'Session 2');
+        vi.setSystemTime(3_000);
+        mockACPClient.createSession.mockResolvedValue('session-3');
+        await sessionManager.createSession('/test/workflow1.py', 'Session 3');
+      } finally {
+        vi.useRealTimers();
+      }
 
       const sessions = sessionManager.getSessionsForWorkflow('/test/workflow1.py');
 
       expect(sessions).toHaveLength(2);
       // Sessions are sorted by updatedAt descending (most recent first)
-      expect(sessions.map((s) => s.name)).toEqual(['Session 1', 'Session 3']);
+      expect(sessions.map((s) => s.name)).toEqual(['Session 3', 'Session 1']);
+    });
+
+    it('should put the later of two sessions with the same time first', async () => {
+      vi.useFakeTimers({ toFake: ['Date'] });
+      try {
+        vi.setSystemTime(5_000);
+        await sessionManager.createSession('/test/same.py', 'Earlier');
+        mockACPClient.createSession.mockResolvedValue('session-later');
+        await sessionManager.createSession('/test/same.py', 'Later');
+      } finally {
+        vi.useRealTimers();
+      }
+
+      expect(sessionManager.getSessionsForWorkflow('/test/same.py').map((s) => s.name)).toEqual(['Later', 'Earlier']);
     });
 
     it('should return empty array for workflow with no sessions', () => {