diff --git a/backend/tests/test_doctor.py b/backend/tests/test_doctor.py
index 5d2e9fab64..b7e68e7ad2 100644
--- a/backend/tests/test_doctor.py
+++ b/backend/tests/test_doctor.py
@@ -1179,4 +1179,4 @@ class TestMainConfigResolution:
         else:
             assert exit_code == 1
             assert "✗ config.yaml found" in output
-            assert "~/cfg.yaml" in output
+            assert str(Path("~/cfg.yaml")) in output
diff --git a/backend/tests/test_scheduled_goal_handoff.py b/backend/tests/test_scheduled_goal_handoff.py
index f7213427a1..25f3d7c76c 100644
--- a/backend/tests/test_scheduled_goal_handoff.py
+++ b/backend/tests/test_scheduled_goal_handoff.py
@@ -468,6 +468,11 @@ async def test_scheduled_cleanup_barrier_keeps_lease_renewal_and_remote_cancel_a
     record = await manager.create_or_reject("result", user_id="alice")
     record.scheduled_goal_cleanup_pending = True
     await manager.set_status(record.run_id, RunStatus.success, persist=False)
+    # Keep the confirmed deadline well inside the 30-second lease window.
+    # Renewal computes a fresh now+lease value; Windows' coarse clock can
+    # otherwise make two immediate samples identical and defeat a strict >
+    # assertion without changing the behavior under test.
+    record.lease_expires_at = (datetime.now(UTC) + timedelta(seconds=10)).isoformat()
     original_deadline = record.lease_expires_at
     await store.request_cancel(record.run_id, action="rollback")
     await manager._renew_leases()