feat: default tools (#2485)

* feat: default tools

* fix: tests

* feat scheduler

* fix: scheduler UI

* Agent switch breadcrumbs

* fix: minor fixes to scheduler

* fix: tests

tests/api/user/test_scheduler_dispatcher.py

@@ -0,0 +1,401 @@
+"""Tests for the scheduler dispatcher (engine-level, no Celery worker)."""
+
+from __future__ import annotations
+
+from datetime import datetime, timedelta, timezone
+
+import pytest
+from sqlalchemy import text
+
+from application.api.user.scheduler_dispatcher import dispatch_due_runs
+from application.storage.db.repositories.schedule_runs import (
+    ScheduleRunsRepository,
+)
+from application.storage.db.repositories.schedules import SchedulesRepository
+
+
+def _now() -> datetime:
+    return datetime.now(timezone.utc)
+
+
+def _make_agent(conn, user_id: str = "u1") -> str:
+    row = conn.execute(
+        text(
+            "INSERT INTO agents (user_id, name, status) "
+            "VALUES (:u, 'a', 'draft') RETURNING id"
+        ),
+        {"u": user_id},
+    ).fetchone()
+    return str(row[0])
+
+
+@pytest.fixture
+def patched_engine(pg_engine, monkeypatch):
+    monkeypatch.setattr(
+        "application.api.user.scheduler_dispatcher.get_engine",
+        lambda: pg_engine,
+    )
+    yield pg_engine
+
+
+@pytest.fixture
+def stub_enqueue(monkeypatch):
+    """Capture every execute_scheduled_run.apply_async."""
+    enqueued: list[str] = []
+
+    class _Task:
+        @staticmethod
+        def apply_async(args=None, **kwargs):
+            if args:
+                enqueued.append(args[0])
+
+    monkeypatch.setattr(
+        "application.api.user.tasks.execute_scheduled_run", _Task
+    )
+    return enqueued
+
+
+def _create_schedule(engine, **kwargs):
+    with engine.begin() as conn:
+        return SchedulesRepository(conn).create(**kwargs)
+
+
+def _set_postgres_uri(monkeypatch, pg_engine):
+    monkeypatch.setattr(
+        "application.api.user.scheduler_dispatcher.settings",
+        type("S", (), {
+            "POSTGRES_URI": str(pg_engine.url),
+            "SCHEDULE_MISFIRE_GRACE": 60,
+        })(),
+    )
+
+
+class TestDispatcherBasic:
+    def test_due_recurring_enqueues_once_and_advances(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        _set_postgres_uri(monkeypatch, pg_engine)
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() - timedelta(seconds=5),
+        )
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 1
+        assert len(stub_enqueue) == 1
+        with pg_engine.connect() as conn:
+            row = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert row["next_run_at"] is not None
+
+    def test_once_dispatch_nulls_next_run_at_keeps_active(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        """Once: dispatcher nulls next_run_at but leaves status='active' for the worker."""
+        _set_postgres_uri(monkeypatch, pg_engine)
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u1", agent_id=agent_id, trigger_type="once",
+            instruction="i", run_at=_now() + timedelta(seconds=1),
+            next_run_at=_now() - timedelta(seconds=5),
+        )
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 1
+        with pg_engine.connect() as conn:
+            row = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert row["status"] == "active"
+        assert row["next_run_at"] is None
+
+
+class TestDedupConstraint:
+    def test_double_dispatch_only_one_run(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        _set_postgres_uri(monkeypatch, pg_engine)
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="*/5 * * * *",
+            next_run_at=_now() - timedelta(seconds=2),
+        )
+        # Pre-claim simulates a racing dispatcher tick.
+        with pg_engine.begin() as conn:
+            row = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+            ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]),
+                "u1",
+                str(row["agent_id"]),
+                row["next_run_at"],
+            )
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 0
+        assert stub_enqueue == []
+
+
+class TestMisfireGrace:
+    def test_stale_tick_recorded_skipped(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        _set_postgres_uri(monkeypatch, pg_engine)
+        monkeypatch.setattr(
+            "application.api.user.scheduler_dispatcher.settings",
+            type("S", (), {
+                "POSTGRES_URI": str(pg_engine.url),
+                "SCHEDULE_MISFIRE_GRACE": 30,
+            })(),
+        )
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="*/5 * * * *",
+            next_run_at=_now() - timedelta(hours=2),
+        )
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 0
+        assert counts["skipped"] >= 1
+        with pg_engine.connect() as conn:
+            runs = ScheduleRunsRepository(conn).list_runs(
+                str(schedule["id"]), "u1",
+            )
+        assert any(r["error_type"] == "missed" for r in runs)
+
+
+class TestOverlap:
+    def test_active_run_blocks_dispatch(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        _set_postgres_uri(monkeypatch, pg_engine)
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="*/5 * * * *",
+            next_run_at=_now() - timedelta(seconds=2),
+        )
+        # Pre-create a running run with a different scheduled_for so overlap fires.
+        with pg_engine.begin() as conn:
+            row = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]),
+                "u1",
+                str(agent_id),
+                _now() - timedelta(minutes=10),
+            )
+            ScheduleRunsRepository(conn).mark_running(row["id"], "t1")
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 0
+
+    def test_once_overlap_clears_next_run_at(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        """Once + overlap nulls next_run_at so the dispatcher stops re-picking."""
+        _set_postgres_uri(monkeypatch, pg_engine)
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u1", agent_id=agent_id, trigger_type="once",
+            instruction="i", run_at=_now() + timedelta(seconds=30),
+            next_run_at=_now() - timedelta(seconds=5),
+        )
+        with pg_engine.begin() as conn:
+            existing = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]),
+                "u1",
+                str(agent_id),
+                _now() - timedelta(minutes=10),
+            )
+            ScheduleRunsRepository(conn).mark_running(existing["id"], "t-prev")
+        dispatch_due_runs()
+        with pg_engine.connect() as conn:
+            row = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert row["status"] == "active"
+        assert row["next_run_at"] is None
+
+
+class TestAgentlessSchedules:
+    def test_dispatcher_claims_and_enqueues_agentless_once(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        """``agent_id IS NULL`` rows are claimed like any other once-schedule."""
+        _set_postgres_uri(monkeypatch, pg_engine)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u-agentless", agent_id=None, trigger_type="once",
+            instruction="agentless ping",
+            run_at=_now() + timedelta(seconds=30),
+            next_run_at=_now() - timedelta(seconds=5),
+            origin_conversation_id=None,
+            created_via="chat",
+        )
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 1
+        assert len(stub_enqueue) == 1
+        with pg_engine.connect() as conn:
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+            run_row = conn.execute(
+                text(
+                    "SELECT * FROM schedule_runs "
+                    "WHERE schedule_id = CAST(:s AS uuid)"
+                ),
+                {"s": str(schedule["id"])},
+            ).fetchone()
+        # Once: dispatcher nulled next_run_at, schedule still active.
+        assert sched["status"] == "active"
+        assert sched["next_run_at"] is None
+        # The pending run carries NULL agent_id (matches the parent).
+        assert run_row._mapping["agent_id"] is None
+        assert run_row._mapping["user_id"] == "u-agentless"
+
+
+class TestAgentlessRoundTrip:
+    """Agentless chat → tool → dispatcher → headless run → message appended."""
+
+    def test_agentless_dispatch_executes_and_appends_message(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        from unittest.mock import patch
+
+        from application.api.user.scheduler_worker import (
+            execute_scheduled_run_body,
+        )
+
+        _set_postgres_uri(monkeypatch, pg_engine)
+        monkeypatch.setattr(
+            "application.api.user.scheduler_worker.get_engine",
+            lambda: pg_engine,
+        )
+        monkeypatch.setattr(
+            "application.api.user.scheduler_worker.settings",
+            type("S", (), {
+                "POSTGRES_URI": str(pg_engine.url),
+                "SCHEDULE_AUTOPAUSE_FAILURES": 3,
+            })(),
+        )
+        monkeypatch.setattr(
+            "application.api.user.scheduler_worker.publish_user_event",
+            lambda *a, **k: "1-0",
+        )
+
+        with pg_engine.begin() as conn:
+            conv_id = conn.execute(
+                text(
+                    "INSERT INTO conversations (user_id, name) "
+                    "VALUES ('u-e2e', 'agentless-chat') RETURNING id"
+                )
+            ).fetchone()[0]
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u-e2e", agent_id=None, trigger_type="once",
+            instruction="ping later",
+            run_at=_now() + timedelta(seconds=30),
+            next_run_at=_now() - timedelta(seconds=5),
+            origin_conversation_id=str(conv_id),
+            created_via="chat",
+        )
+
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 1
+        run_id = stub_enqueue[0]
+
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            return_value={
+                "answer": "agentless e2e done",
+                "tool_calls": [], "sources": [], "thought": "",
+                "prompt_tokens": 1, "generated_tokens": 1,
+                "denied": [], "error_type": None, "model_id": "fake",
+            },
+        ):
+            result = execute_scheduled_run_body(run_id, "celery-e2e")
+        assert result["status"] == "success"
+
+        with pg_engine.connect() as conn:
+            run = ScheduleRunsRepository(conn).get_internal(run_id)
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+            messages = conn.execute(
+                text(
+                    "SELECT * FROM conversation_messages "
+                    "WHERE conversation_id = CAST(:c AS uuid)"
+                ),
+                {"c": str(conv_id)},
+            ).fetchall()
+        assert run["status"] == "success"
+        assert run["agent_id"] is None
+        assert sched["status"] == "completed"
+        assert sched["agent_id"] is None
+        assert len(messages) == 1
+        meta = messages[0]._mapping["message_metadata"]
+        assert meta.get("scheduled") is True
+
+
+class TestOnceRoundTrip:
+    """End-to-end: chat-driven once-schedule executes and the schedule completes."""
+
+    def test_once_dispatch_executes_and_completes_schedule(
+        self, pg_engine, patched_engine, stub_enqueue, monkeypatch,
+    ):
+        from unittest.mock import patch
+
+        from application.api.user.scheduler_worker import (
+            execute_scheduled_run_body,
+        )
+
+        _set_postgres_uri(monkeypatch, pg_engine)
+        monkeypatch.setattr(
+            "application.api.user.scheduler_worker.get_engine",
+            lambda: pg_engine,
+        )
+        monkeypatch.setattr(
+            "application.api.user.scheduler_worker.settings",
+            type("S", (), {
+                "POSTGRES_URI": str(pg_engine.url),
+                "SCHEDULE_AUTOPAUSE_FAILURES": 3,
+            })(),
+        )
+        monkeypatch.setattr(
+            "application.api.user.scheduler_worker.publish_user_event",
+            lambda *a, **k: "1-0",
+        )
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+        schedule = _create_schedule(
+            pg_engine,
+            user_id="u1", agent_id=agent_id, trigger_type="once",
+            instruction="follow up", run_at=_now() + timedelta(seconds=1),
+            next_run_at=_now() - timedelta(seconds=5),
+        )
+        counts = dispatch_due_runs()
+        assert counts["enqueued"] == 1
+        assert len(stub_enqueue) == 1
+        run_id = stub_enqueue[0]
+        with pg_engine.connect() as conn:
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert sched["status"] == "active"
+        assert sched["next_run_at"] is None
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            return_value={
+                "answer": "done",
+                "tool_calls": [], "sources": [], "thought": "",
+                "prompt_tokens": 1, "generated_tokens": 1,
+                "denied": [], "error_type": None, "model_id": "fake",
+            },
+        ):
+            result = execute_scheduled_run_body(run_id, "celery-c1")
+        assert result["status"] == "success"
+        with pg_engine.connect() as conn:
+            run = ScheduleRunsRepository(conn).get_internal(run_id)
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert run["status"] == "success"
+        assert run["output"] == "done"
+        assert sched["status"] == "completed"
+        assert sched["next_run_at"] is None

tests/api/user/test_scheduler_reconcile.py

@@ -0,0 +1,282 @@
+"""Tests for the scheduler reconciliation sweep + cleanup task."""
+
+from __future__ import annotations
+
+from datetime import datetime, timedelta, timezone
+
+import pytest
+from sqlalchemy import text
+
+from application.api.user.reconciliation import run_reconciliation
+from application.storage.db.repositories.schedule_runs import (
+    ScheduleRunsRepository,
+)
+from application.storage.db.repositories.schedules import SchedulesRepository
+
+
+def _now() -> datetime:
+    return datetime.now(timezone.utc)
+
+
+def _make_pending_run(conn, *, user_id="u1"):
+    agent_id = str(
+        conn.execute(
+            text(
+                "INSERT INTO agents (user_id, name, status) "
+                "VALUES (:u, 'a', 'draft') RETURNING id"
+            ),
+            {"u": user_id},
+        ).fetchone()[0]
+    )
+    schedule = SchedulesRepository(conn).create(
+        user_id=user_id, agent_id=agent_id, trigger_type="recurring",
+        instruction="i", cron="*/5 * * * *",
+        next_run_at=_now() + timedelta(minutes=5),
+    )
+    run = ScheduleRunsRepository(conn).record_pending(
+        str(schedule["id"]), user_id, agent_id, _now(),
+    )
+    return schedule, run, agent_id
+
+
+def _make_once_pending_run(conn, *, user_id="u1"):
+    """Once-schedule + pending run variant of _make_pending_run."""
+    agent_id = str(
+        conn.execute(
+            text(
+                "INSERT INTO agents (user_id, name, status) "
+                "VALUES (:u, 'a', 'draft') RETURNING id"
+            ),
+            {"u": user_id},
+        ).fetchone()[0]
+    )
+    fire = _now() + timedelta(minutes=5)
+    schedule = SchedulesRepository(conn).create(
+        user_id=user_id, agent_id=agent_id, trigger_type="once",
+        instruction="do once", run_at=fire,
+        next_run_at=fire,
+    )
+    run = ScheduleRunsRepository(conn).record_pending(
+        str(schedule["id"]), user_id, agent_id, fire,
+    )
+    return schedule, run, agent_id
+
+
+@pytest.fixture
+def patched_engine(pg_engine, monkeypatch):
+    monkeypatch.setattr(
+        "application.api.user.reconciliation.get_engine",
+        lambda: pg_engine,
+    )
+    monkeypatch.setattr(
+        "application.api.user.reconciliation.settings",
+        type("S", (), {
+            "POSTGRES_URI": str(pg_engine.url),
+            "SCHEDULE_RUN_TIMEOUT": 60,
+        })(),
+    )
+    yield pg_engine
+
+
+class TestReconciler:
+    def test_stuck_running_flipped_to_timeout(self, pg_engine, patched_engine):
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_pending_run(conn)
+            ScheduleRunsRepository(conn).mark_running(run["id"], "t1")
+            conn.execute(
+                text(
+                    "UPDATE schedule_runs "
+                    "SET started_at = now() - interval '120 minutes' "
+                    "WHERE id = CAST(:i AS uuid)"
+                ),
+                {"i": run["id"]},
+            )
+
+        summary = run_reconciliation()
+        assert summary["schedule_runs_failed"] >= 1
+        with pg_engine.connect() as conn:
+            row = ScheduleRunsRepository(conn).get_internal(run["id"])
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert row["status"] == "timeout"
+        assert row["error_type"] == "timeout"
+        assert sched["consecutive_failure_count"] == 1
+
+    def test_stuck_pending_flipped_to_failed(self, pg_engine, patched_engine):
+        """A pending run whose worker never started reconciles to 'failed'."""
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_pending_run(conn)
+            conn.execute(
+                text(
+                    "UPDATE schedule_runs "
+                    "SET created_at = now() - interval '120 minutes' "
+                    "WHERE id = CAST(:i AS uuid)"
+                ),
+                {"i": run["id"]},
+            )
+
+        summary = run_reconciliation()
+        assert summary["schedule_runs_failed"] >= 1
+        with pg_engine.connect() as conn:
+            row = ScheduleRunsRepository(conn).get_internal(run["id"])
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert row["status"] == "failed"
+        assert row["error_type"] == "internal"
+        assert "worker_never_started" in (row["error"] or "")
+        assert sched["consecutive_failure_count"] == 1
+
+    def test_once_schedule_with_stuck_running_run_marked_completed(
+        self, pg_engine, patched_engine,
+    ):
+        """Once + stuck 'running' run -> parent flipped to 'completed'."""
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_once_pending_run(conn)
+            ScheduleRunsRepository(conn).mark_running(run["id"], "t-once")
+            conn.execute(
+                text(
+                    "UPDATE schedule_runs "
+                    "SET started_at = now() - interval '120 minutes' "
+                    "WHERE id = CAST(:i AS uuid)"
+                ),
+                {"i": run["id"]},
+            )
+
+        run_reconciliation()
+        with pg_engine.connect() as conn:
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+            row = ScheduleRunsRepository(conn).get_internal(run["id"])
+        assert row["status"] == "timeout"
+        assert sched["status"] == "completed", (
+            "stuck once-run must terminal-flip the parent schedule"
+        )
+        assert sched["next_run_at"] is None
+
+    def test_once_schedule_with_stuck_pending_run_marked_completed(
+        self, pg_engine, patched_engine,
+    ):
+        """Once + stuck 'pending' run -> parent flipped to 'completed'."""
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_once_pending_run(conn)
+            conn.execute(
+                text(
+                    "UPDATE schedule_runs "
+                    "SET created_at = now() - interval '120 minutes' "
+                    "WHERE id = CAST(:i AS uuid)"
+                ),
+                {"i": run["id"]},
+            )
+
+        run_reconciliation()
+        with pg_engine.connect() as conn:
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+            row = ScheduleRunsRepository(conn).get_internal(run["id"])
+        assert row["status"] == "failed"
+        assert sched["status"] == "completed", (
+            "stuck pending once-run must terminal-flip the parent schedule"
+        )
+        assert sched["next_run_at"] is None
+
+    def test_agentless_once_stuck_running_marked_completed(
+        self, pg_engine, patched_engine,
+    ):
+        """Stuck-run terminal flip works for agentless once-schedules."""
+        with pg_engine.begin() as conn:
+            fire = _now() + timedelta(minutes=5)
+            schedule = SchedulesRepository(conn).create(
+                user_id="u-agentless", agent_id=None, trigger_type="once",
+                instruction="agentless go", run_at=fire,
+                next_run_at=fire,
+                created_via="chat",
+            )
+            run = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]), "u-agentless", None, fire,
+            )
+            ScheduleRunsRepository(conn).mark_running(run["id"], "t-stuck")
+            conn.execute(
+                text(
+                    "UPDATE schedule_runs "
+                    "SET started_at = now() - interval '120 minutes' "
+                    "WHERE id = CAST(:i AS uuid)"
+                ),
+                {"i": run["id"]},
+            )
+
+        run_reconciliation()
+        with pg_engine.connect() as conn:
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+            row = ScheduleRunsRepository(conn).get_internal(run["id"])
+        assert row["status"] == "timeout"
+        assert sched["status"] == "completed"
+        assert sched["next_run_at"] is None
+
+    def test_recurring_schedule_with_stuck_run_stays_active(
+        self, pg_engine, patched_engine,
+    ):
+        """Recurring keeps firing; only the run flips, not the parent."""
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_pending_run(conn)
+            ScheduleRunsRepository(conn).mark_running(run["id"], "t-rec")
+            conn.execute(
+                text(
+                    "UPDATE schedule_runs "
+                    "SET started_at = now() - interval '120 minutes' "
+                    "WHERE id = CAST(:i AS uuid)"
+                ),
+                {"i": run["id"]},
+            )
+
+        run_reconciliation()
+        with pg_engine.connect() as conn:
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert sched["status"] == "active"
+        assert sched["consecutive_failure_count"] == 1
+
+
+class TestCleanup:
+    def test_cleanup_schedule_runs_trims_old_rows(self, pg_engine, monkeypatch):
+        from application.api.user.tasks import cleanup_schedule_runs as _task
+
+        monkeypatch.setattr(
+            "application.storage.db.engine.get_engine",
+            lambda: pg_engine,
+        )
+
+        class S:
+            POSTGRES_URI = str(pg_engine.url)
+            SCHEDULE_RUN_OUTPUT_RETENTION_DAYS = 30
+        monkeypatch.setattr("application.api.user.tasks.settings", S, raising=False)
+        monkeypatch.setattr(
+            "application.core.settings.settings.POSTGRES_URI",
+            str(pg_engine.url),
+            raising=False,
+        )
+        monkeypatch.setattr(
+            "application.core.settings.settings.SCHEDULE_RUN_OUTPUT_RETENTION_DAYS",
+            30,
+            raising=False,
+        )
+
+        with pg_engine.begin() as conn:
+            schedule, _, _ = _make_pending_run(conn)
+            for i in range(60):
+                conn.execute(
+                    text(
+                        """
+                        INSERT INTO schedule_runs (
+                            schedule_id, user_id, agent_id, status,
+                            scheduled_for, created_at
+                        ) VALUES (
+                            CAST(:s AS uuid), 'u1',
+                            CAST(:a AS uuid), 'success',
+                            now() - interval '100 days' - (:i * interval '1 second'),
+                            now() - interval '100 days'
+                        )
+                        """
+                    ),
+                    {"s": str(schedule["id"]),
+                     "a": str(schedule["agent_id"]),
+                     "i": i},
+                )
+
+        result = _task.run()
+        assert isinstance(result.get("deleted"), int)
+        assert result["deleted"] >= 1

tests/api/user/test_scheduler_worker.py

@@ -0,0 +1,428 @@
+"""Tests for execute_scheduled_run_body (mocked agent run)."""
+
+from __future__ import annotations
+
+from datetime import datetime, timedelta, timezone
+from unittest.mock import patch
+
+import pytest
+from sqlalchemy import text
+
+from application.api.user.scheduler_worker import execute_scheduled_run_body
+from application.storage.db.repositories.schedule_runs import (
+    ScheduleRunsRepository,
+)
+from application.storage.db.repositories.schedules import SchedulesRepository
+
+
+def _now() -> datetime:
+    return datetime.now(timezone.utc)
+
+
+def _make_agent(conn, user_id: str = "u1") -> str:
+    row = conn.execute(
+        text(
+            "INSERT INTO agents (user_id, name, status, default_model_id) "
+            "VALUES (:u, 'a', 'draft', '') RETURNING id"
+        ),
+        {"u": user_id},
+    ).fetchone()
+    return str(row[0])
+
+
+def _make_pending_run(conn, *, user_id="u1"):
+    agent_id = _make_agent(conn, user_id)
+    schedule = SchedulesRepository(conn).create(
+        user_id=user_id, agent_id=agent_id, trigger_type="recurring",
+        instruction="hello", cron="* * * * *",
+        next_run_at=_now() + timedelta(minutes=5),
+    )
+    run = ScheduleRunsRepository(conn).record_pending(
+        str(schedule["id"]),
+        user_id,
+        agent_id,
+        _now(),
+    )
+    return schedule, run, agent_id
+
+
+@pytest.fixture
+def patched_engine(pg_engine, monkeypatch):
+    monkeypatch.setattr(
+        "application.api.user.scheduler_worker.get_engine",
+        lambda: pg_engine,
+    )
+    monkeypatch.setattr(
+        "application.api.user.scheduler_worker.settings",
+        type("S", (), {
+            "POSTGRES_URI": str(pg_engine.url),
+            "SCHEDULE_AUTOPAUSE_FAILURES": 2,
+        })(),
+    )
+    yield pg_engine
+
+
+@pytest.fixture
+def stub_events(monkeypatch):
+    captured: list[tuple] = []
+
+    def _fake_publish(user_id, event_type, payload, *, scope=None):
+        captured.append((event_type, payload, scope))
+        return "1-0"
+
+    monkeypatch.setattr(
+        "application.api.user.scheduler_worker.publish_user_event",
+        _fake_publish,
+    )
+    return captured
+
+
+class TestExecuteScheduledRunBody:
+    def test_success_flow(self, pg_engine, patched_engine, stub_events):
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_pending_run(conn)
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            return_value={
+                "answer": "all done",
+                "tool_calls": [],
+                "sources": [],
+                "thought": "",
+                "prompt_tokens": 10,
+                "generated_tokens": 5,
+                "denied": [],
+                "error_type": None,
+                "model_id": "fake-model",
+            },
+        ):
+            result = execute_scheduled_run_body(str(run["id"]), "celery-1")
+        assert result["status"] == "success"
+        with pg_engine.connect() as conn:
+            row = ScheduleRunsRepository(conn).get_internal(str(run["id"]))
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert row["status"] == "success"
+        assert row["output"] == "all done"
+        assert row["prompt_tokens"] == 10
+        assert sched["consecutive_failure_count"] == 0
+        event_types = [e[0] for e in stub_events]
+        assert "schedule.run.completed" in event_types
+
+    def test_agent_exception_marks_failed_and_bumps(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_pending_run(conn)
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            side_effect=RuntimeError("boom"),
+        ):
+            result = execute_scheduled_run_body(str(run["id"]), "celery-2")
+        assert result["status"] == "failed"
+        with pg_engine.connect() as conn:
+            row = ScheduleRunsRepository(conn).get_internal(str(run["id"]))
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert row["status"] == "failed"
+        assert row["error_type"] == "agent_error"
+        assert sched["consecutive_failure_count"] == 1
+        assert "schedule.run.failed" in {e[0] for e in stub_events}
+
+    def test_autopause_after_threshold(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        with pg_engine.begin() as conn:
+            schedule, run, agent_id = _make_pending_run(conn)
+            SchedulesRepository(conn).bump_failure_count(str(schedule["id"]))
+            another_run = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]),
+                "u1",
+                agent_id,
+                _now() + timedelta(seconds=1),
+            )
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            side_effect=RuntimeError("boom"),
+        ):
+            execute_scheduled_run_body(str(another_run["id"]), "celery-3")
+        with pg_engine.connect() as conn:
+            sched = SchedulesRepository(conn).get_internal(str(schedule["id"]))
+        assert sched["status"] == "paused"
+        assert "schedule.autopaused" in {e[0] for e in stub_events}
+
+    def test_denied_with_empty_output_marks_tool_not_allowed(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        with pg_engine.begin() as conn:
+            schedule, run, _ = _make_pending_run(conn)
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            return_value={
+                "answer": "",
+                "tool_calls": [],
+                "sources": [],
+                "thought": "",
+                "prompt_tokens": 1,
+                "generated_tokens": 0,
+                "denied": [{"tool_name": "telegram"}],
+                "error_type": "tool_not_allowed",
+                "model_id": "fake",
+            },
+        ):
+            execute_scheduled_run_body(str(run["id"]), "celery-4")
+        with pg_engine.connect() as conn:
+            row = ScheduleRunsRepository(conn).get_internal(str(run["id"]))
+        assert row["status"] == "failed"
+        assert row["error_type"] == "tool_not_allowed"
+
+    def test_one_time_loads_chat_history(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+            schedule = SchedulesRepository(conn).create(
+                user_id="u1", agent_id=agent_id, trigger_type="once",
+                instruction="follow up", run_at=_now() + timedelta(seconds=5),
+                next_run_at=_now(),
+            )
+            conv_id = conn.execute(
+                text(
+                    "INSERT INTO conversations (user_id, agent_id, name) "
+                    "VALUES ('u1', CAST(:a AS uuid), 'origin') RETURNING id"
+                ),
+                {"a": agent_id},
+            ).fetchone()[0]
+            SchedulesRepository(conn).update_internal(
+                str(schedule["id"]),
+                {"origin_conversation_id": str(conv_id)},
+            )
+            conn.execute(
+                text(
+                    """
+                    INSERT INTO conversation_messages
+                        (conversation_id, position, prompt, response, user_id)
+                    VALUES (CAST(:c AS uuid), 0, 'hello', 'hi', 'u1')
+                    """
+                ),
+                {"c": str(conv_id)},
+            )
+            run = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]), "u1", agent_id, _now(),
+            )
+        captured: dict = {}
+        def _fake_run(agent_config, query, **kwargs):
+            captured.update(kwargs)
+            return {
+                "answer": "follow-up answer",
+                "tool_calls": [], "sources": [], "thought": "",
+                "prompt_tokens": 1, "generated_tokens": 1,
+                "denied": [], "error_type": None, "model_id": "fake",
+            }
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless", _fake_run,
+        ):
+            execute_scheduled_run_body(str(run["id"]), "celery-h")
+        assert len(captured.get("chat_history", [])) == 1
+        assert captured["chat_history"][0]["prompt"] == "hello"
+
+    def test_agentless_schedule_uses_system_defaults_and_appends(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        """Agentless ``once`` schedule → ephemeral classic agent → message appended."""
+        with pg_engine.begin() as conn:
+            conv_id = conn.execute(
+                text(
+                    "INSERT INTO conversations (user_id, name) "
+                    "VALUES ('u1', 'agentless-origin') RETURNING id"
+                )
+            ).fetchone()[0]
+            schedule = SchedulesRepository(conn).create(
+                user_id="u1", agent_id=None, trigger_type="once",
+                instruction="follow up agentless",
+                run_at=_now() + timedelta(seconds=5),
+                next_run_at=_now(),
+                origin_conversation_id=str(conv_id),
+                created_via="chat",
+            )
+            run = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]), "u1", None, _now(),
+            )
+        captured: dict = {}
+
+        def _fake_run(agent_config, query, **kwargs):
+            captured["agent_config"] = agent_config
+            captured["kwargs"] = kwargs
+            return {
+                "answer": "agentless ran",
+                "tool_calls": [], "sources": [], "thought": "",
+                "prompt_tokens": 4, "generated_tokens": 6,
+                "denied": [], "error_type": None, "model_id": "fake",
+            }
+
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            _fake_run,
+        ):
+            result = execute_scheduled_run_body(str(run["id"]), "celery-agentless")
+        assert result["status"] == "success"
+        # Ephemeral classic config: no source, default retriever, no agent id.
+        cfg = captured["agent_config"]
+        assert cfg["id"] is None
+        assert cfg["user_id"] == "u1"
+        assert cfg["agent_type"] == "classic"
+        assert cfg["retriever"] == "classic"
+        assert cfg["prompt_id"] == "default"
+        with pg_engine.connect() as conn:
+            row = ScheduleRunsRepository(conn).get_internal(str(run["id"]))
+            messages = conn.execute(
+                text(
+                    "SELECT * FROM conversation_messages "
+                    "WHERE conversation_id = CAST(:c AS uuid)"
+                ),
+                {"c": str(conv_id)},
+            ).fetchall()
+        assert row["status"] == "success"
+        assert row["output"] == "agentless ran"
+        assert row["conversation_id"] is not None
+        assert len(messages) == 1
+        # The published event payload tolerates a NULL agent_id.
+        appended_events = [e for e in stub_events if e[0] == "schedule.message.appended"]
+        assert appended_events
+
+    def test_agentless_ephemeral_config_omits_tools_snapshot(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        """Dead ``tools`` snapshot dropped — toolset is rebuilt at fire time."""
+        with pg_engine.begin() as conn:
+            conv_id = conn.execute(
+                text(
+                    "INSERT INTO conversations (user_id, name) "
+                    "VALUES ('u1', 'no-tools-snap') RETURNING id"
+                )
+            ).fetchone()[0]
+            schedule = SchedulesRepository(conn).create(
+                user_id="u1", agent_id=None, trigger_type="once",
+                instruction="x", run_at=_now() + timedelta(seconds=5),
+                next_run_at=_now(),
+                origin_conversation_id=str(conv_id),
+                created_via="chat",
+            )
+            run = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]), "u1", None, _now(),
+            )
+        captured: dict = {}
+
+        def _fake_run(agent_config, query, **kwargs):
+            captured["agent_config"] = agent_config
+            return {
+                "answer": "ok", "tool_calls": [], "sources": [], "thought": "",
+                "prompt_tokens": 1, "generated_tokens": 1,
+                "denied": [], "error_type": None, "model_id": "fake",
+            }
+
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            _fake_run,
+        ):
+            execute_scheduled_run_body(str(run["id"]), "celery-no-snap")
+        cfg = captured["agent_config"]
+        # ``tools`` MUST NOT be in the ephemeral shape — the runtime
+        # toolset is rebuilt by ``ToolExecutor`` (which honours headless
+        # filtering for chat-only tools like ``scheduler``).
+        assert "tools" not in cfg
+
+    def test_agentless_token_usage_row_has_null_agent_id(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        """token_usage row for an agentless run carries ``agent_id IS NULL``."""
+        with pg_engine.begin() as conn:
+            conv_id = conn.execute(
+                text(
+                    "INSERT INTO conversations (user_id, name) "
+                    "VALUES ('u1', 'agentless-tu') RETURNING id"
+                )
+            ).fetchone()[0]
+            schedule = SchedulesRepository(conn).create(
+                user_id="u1", agent_id=None, trigger_type="once",
+                instruction="tu", run_at=_now() + timedelta(seconds=5),
+                next_run_at=_now(),
+                origin_conversation_id=str(conv_id),
+                created_via="chat",
+            )
+            run = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]), "u1", None, _now(),
+            )
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            return_value={
+                "answer": "yes",
+                "tool_calls": [], "sources": [], "thought": "",
+                "prompt_tokens": 11, "generated_tokens": 7,
+                "denied": [], "error_type": None, "model_id": "fake",
+            },
+        ):
+            execute_scheduled_run_body(str(run["id"]), "celery-tu")
+        with pg_engine.connect() as conn:
+            tu_row = conn.execute(
+                text(
+                    "SELECT * FROM token_usage "
+                    "WHERE request_id = :r"
+                ),
+                {"r": str(run["id"])},
+            ).fetchone()
+        assert tu_row is not None
+        assert tu_row._mapping["agent_id"] is None
+        assert tu_row._mapping["source"] == "schedule"
+
+    def test_one_time_appends_message(
+        self, pg_engine, patched_engine, stub_events,
+    ):
+        with pg_engine.begin() as conn:
+            agent_id = _make_agent(conn)
+            schedule = SchedulesRepository(conn).create(
+                user_id="u1", agent_id=agent_id, trigger_type="once",
+                instruction="hello", run_at=_now() + timedelta(seconds=5),
+                next_run_at=_now(),
+            )
+            conv_id = conn.execute(
+                text(
+                    "INSERT INTO conversations (user_id, agent_id, name) "
+                    "VALUES ('u1', CAST(:a AS uuid), 'origin') RETURNING id"
+                ),
+                {"a": agent_id},
+            ).fetchone()[0]
+            SchedulesRepository(conn).update_internal(
+                str(schedule["id"]),
+                {"origin_conversation_id": str(conv_id)},
+            )
+            run = ScheduleRunsRepository(conn).record_pending(
+                str(schedule["id"]), "u1", agent_id, _now(),
+            )
+        with patch(
+            "application.api.user.scheduler_worker.run_agent_headless",
+            return_value={
+                "answer": "scheduled answer",
+                "tool_calls": [],
+                "sources": [],
+                "thought": "",
+                "prompt_tokens": 2,
+                "generated_tokens": 3,
+                "denied": [],
+                "error_type": None,
+                "model_id": "fake",
+            },
+        ):
+            execute_scheduled_run_body(str(run["id"]), "celery-5")
+        with pg_engine.connect() as conn:
+            row = ScheduleRunsRepository(conn).get_internal(str(run["id"]))
+            messages = conn.execute(
+                text(
+                    "SELECT * FROM conversation_messages "
+                    "WHERE conversation_id = CAST(:c AS uuid)"
+                ),
+                {"c": str(conv_id)},
+            ).fetchall()
+        assert row["conversation_id"] is not None
+        assert row["message_id"] is not None
+        assert len(messages) == 1
+        meta = messages[0]._mapping["message_metadata"]
+        assert meta.get("scheduled") is True
+        assert "schedule.message.appended" in {e[0] for e in stub_events}

tests/api/user/test_schedules_routes.py

@@ -0,0 +1,508 @@
+"""Tests for the schedules REST API."""
+
+from __future__ import annotations
+
+from contextlib import contextmanager
+from datetime import datetime, timedelta, timezone
+from unittest.mock import patch
+
+import pytest
+from flask import Flask
+from sqlalchemy import text
+
+from application.storage.db.repositories.schedules import SchedulesRepository
+
+
+@pytest.fixture
+def app():
+    return Flask(__name__)
+
+
+@contextmanager
+def _patch_db(conn):
+    @contextmanager
+    def _yield():
+        yield conn
+
+    with patch(
+        "application.api.user.schedules.routes.db_session", _yield,
+    ), patch(
+        "application.api.user.schedules.routes.db_readonly", _yield,
+    ):
+        yield
+
+
+def _now() -> datetime:
+    return datetime.now(timezone.utc)
+
+
+def _make_agent(conn, user_id: str = "u1") -> str:
+    row = conn.execute(
+        text(
+            "INSERT INTO agents (user_id, name, status) "
+            "VALUES (:u, 'a', 'draft') RETURNING id"
+        ),
+        {"u": user_id},
+    ).fetchone()
+    return str(row[0])
+
+
+class TestCreateRecurring:
+    def test_unauthorized(self, app):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        with app.test_request_context(
+            "/api/agents/x/schedules", method="POST", json={},
+        ):
+            from flask import request
+            request.decoded_token = None
+            resp = AgentSchedules().post("x")
+        assert resp.status_code == 401
+
+    def test_agent_not_found(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        with _patch_db(pg_conn), app.test_request_context(
+            "/api/agents/00000000-0000-0000-0000-000000000000/schedules",
+            method="POST", json={"instruction": "x", "cron": "* * * * *"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(
+                "00000000-0000-0000-0000-000000000000",
+            )
+        assert resp.status_code == 404
+
+    def test_invalid_cron(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules",
+            method="POST",
+            json={"instruction": "x", "cron": "not a cron"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(agent_id)
+        assert resp.status_code == 400
+
+    def test_create_success(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules",
+            method="POST",
+            json={
+                "instruction": "weekly digest",
+                "cron": "0 9 * * 1",
+                "timezone": "Europe/Warsaw",
+                "tool_allowlist": [],
+            },
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(agent_id)
+        assert resp.status_code == 201
+        body = resp.get_json()
+        assert body["schedule"]["cron"] == "0 9 * * 1"
+        assert body["schedule"]["timezone"] == "Europe/Warsaw"
+
+
+class TestCreateOnce:
+    def test_creates_once_with_run_at(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        run_at = (_now() + timedelta(hours=2)).isoformat().replace(
+            "+00:00", "Z",
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules",
+            method="POST",
+            json={
+                "instruction": "remind me",
+                "trigger_type": "once",
+                "run_at": run_at,
+                "timezone": "UTC",
+                "tool_allowlist": [],
+            },
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(agent_id)
+        assert resp.status_code == 201
+        body = resp.get_json()
+        assert body["schedule"]["trigger_type"] == "once"
+        assert body["schedule"]["run_at"] is not None
+
+    def test_once_requires_run_at(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules",
+            method="POST",
+            json={
+                "instruction": "remind me",
+                "trigger_type": "once",
+            },
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(agent_id)
+        assert resp.status_code == 400
+
+    def test_once_rejects_past_run_at(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        past = (_now() - timedelta(hours=1)).isoformat().replace(
+            "+00:00", "Z",
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules",
+            method="POST",
+            json={
+                "instruction": "x",
+                "trigger_type": "once",
+                "run_at": past,
+            },
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(agent_id)
+        assert resp.status_code == 400
+
+    def test_recurring_default_when_trigger_type_omitted(self, app, pg_conn):
+        """Backwards compat: a payload with cron but no trigger_type still works."""
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules",
+            method="POST",
+            json={
+                "instruction": "hourly",
+                "cron": "0 * * * *",
+                "timezone": "UTC",
+            },
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(agent_id)
+        assert resp.status_code == 201
+        assert resp.get_json()["schedule"]["trigger_type"] == "recurring"
+
+
+class TestListForAgent:
+    def test_list(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules", method="GET",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().get(agent_id)
+        assert resp.status_code == 200
+        assert len(resp.get_json()["schedules"]) == 1
+
+
+class TestGetEditPatchDelete:
+    def _make(self, conn, **kwargs):
+        return SchedulesRepository(conn).create(**kwargs)
+
+    def test_get_owner_scoped(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = self._make(
+            pg_conn,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}", method="GET",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u2"}
+            resp = ScheduleResource().get(str(s["id"]))
+        assert resp.status_code == 404
+
+    def test_pause_then_resume(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = self._make(
+            pg_conn,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}",
+            method="PATCH",
+            json={"action": "pause"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().patch(str(s["id"]))
+        assert resp.status_code == 200
+        assert resp.get_json()["schedule"]["status"] == "paused"
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}",
+            method="PATCH",
+            json={"action": "resume"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().patch(str(s["id"]))
+        assert resp.status_code == 200
+        body = resp.get_json()
+        assert body["schedule"]["status"] == "active"
+        assert body["schedule"]["next_run_at"] is not None
+
+    def test_delete_owner_scoped(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = self._make(
+            pg_conn,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}", method="DELETE",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u2"}
+            resp = ScheduleResource().delete(str(s["id"]))
+        assert resp.status_code == 404
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}", method="DELETE",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().delete(str(s["id"]))
+        assert resp.status_code == 200
+
+    def test_put_invalid_cron(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = self._make(
+            pg_conn,
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}",
+            method="PUT", json={"cron": "bad"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().put(str(s["id"]))
+        assert resp.status_code == 400
+
+
+class TestRunNow:
+    def test_runs_returns_202(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleRunNow
+
+        agent_id = _make_agent(pg_conn)
+        s = SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), patch(
+            "application.api.user.tasks.execute_scheduled_run",
+            type("T", (), {"apply_async": staticmethod(lambda **k: None)}),
+        ), app.test_request_context(
+            f"/api/schedules/{s['id']}/run", method="POST",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleRunNow().post(str(s["id"]))
+        assert resp.status_code == 202
+
+    def test_second_run_blocked_by_active(self, app, pg_conn):
+        """Run-Now serializes via FOR UPDATE + has_active_run; second 409s."""
+        from application.api.user.schedules.routes import ScheduleRunNow
+
+        agent_id = _make_agent(pg_conn)
+        s = SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="0 9 * * 1",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), patch(
+            "application.api.user.tasks.execute_scheduled_run",
+            type("T", (), {"apply_async": staticmethod(lambda **k: None)}),
+        ), app.test_request_context(
+            f"/api/schedules/{s['id']}/run", method="POST",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            first = ScheduleRunNow().post(str(s["id"]))
+            assert first.status_code == 202
+            second = ScheduleRunNow().post(str(s["id"]))
+            assert second.status_code == 409
+
+
+class TestMinInterval:
+    def test_create_rejects_below_min_interval(self, app, pg_conn):
+        from application.api.user.schedules.routes import AgentSchedules
+
+        agent_id = _make_agent(pg_conn)
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/agents/{agent_id}/schedules",
+            method="POST",
+            json={"instruction": "x", "cron": "* * * * *"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = AgentSchedules().post(agent_id)
+        assert resp.status_code == 400
+        assert "minimum interval" in resp.get_json()["message"]
+
+    def test_put_rejects_below_min_interval(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="0 9 * * 1",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}", method="PUT",
+            json={"cron": "*/5 * * * *"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().put(str(s["id"]))
+        assert resp.status_code == 400
+        assert "minimum interval" in resp.get_json()["message"]
+
+
+class TestResumeOnceStale:
+    def test_stale_run_at_returns_clear_409(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="once",
+            instruction="i", run_at=_now() + timedelta(hours=1),
+            next_run_at=_now() + timedelta(hours=1),
+            status="paused",
+        )
+        pg_conn.execute(
+            text(
+                "UPDATE schedules SET run_at = now() - interval '1 day' "
+                "WHERE id = CAST(:id AS uuid)"
+            ),
+            {"id": str(s["id"])},
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}", method="PATCH",
+            json={"action": "resume"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().patch(str(s["id"]))
+        assert resp.status_code == 409
+        assert "elapsed" in resp.get_json()["message"]
+
+    def test_resume_accepts_new_run_at(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="once",
+            instruction="i", run_at=_now() + timedelta(hours=1),
+            next_run_at=_now() + timedelta(hours=1),
+            status="paused",
+        )
+        pg_conn.execute(
+            text(
+                "UPDATE schedules SET run_at = now() - interval '1 day' "
+                "WHERE id = CAST(:id AS uuid)"
+            ),
+            {"id": str(s["id"])},
+        )
+        new_run_at = (_now() + timedelta(hours=3)).isoformat()
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}", method="PATCH",
+            json={"action": "resume", "run_at": new_run_at},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().patch(str(s["id"]))
+        assert resp.status_code == 200
+        body = resp.get_json()["schedule"]
+        assert body["status"] == "active"
+
+
+class TestRunList:
+    def test_list_owner_scoped(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleRunList
+
+        agent_id = _make_agent(pg_conn)
+        s = SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+        with _patch_db(pg_conn), app.test_request_context(
+            f"/api/schedules/{s['id']}/runs", method="GET",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u2"}
+            resp = ScheduleRunList().get(str(s["id"]))
+        assert resp.status_code == 404
+
+
+class TestUnexpectedExceptionMasked:
+    """Unexpected exceptions log full trace + return generic 500 (no leak)."""
+
+    def test_unexpected_repo_error_returns_generic_500(self, app, pg_conn):
+        from application.api.user.schedules.routes import ScheduleResource
+
+        agent_id = _make_agent(pg_conn)
+        s = SchedulesRepository(pg_conn).create(
+            user_id="u1", agent_id=agent_id, trigger_type="recurring",
+            instruction="i", cron="* * * * *",
+            next_run_at=_now() + timedelta(hours=1),
+        )
+
+        # Mock the repo's ``get`` to raise an unexpected RuntimeError carrying
+        # internal-sounding detail; the response must NOT echo that string.
+        def _boom(*args, **kwargs):
+            raise RuntimeError("internal detail: secret connection string")
+
+        with _patch_db(pg_conn), patch.object(
+            SchedulesRepository, "get", side_effect=_boom,
+        ), app.test_request_context(
+            f"/api/schedules/{s['id']}", method="GET",
+        ):
+            from flask import request
+            request.decoded_token = {"sub": "u1"}
+            resp = ScheduleResource().get(str(s["id"]))
+        assert resp.status_code == 500
+        body = resp.get_json()
+        assert body["success"] is False
+        assert body["message"] == "internal error"
+        # Defensive: the internal-sounding detail must not leak through.
+        assert "secret connection string" not in resp.get_data(as_text=True)

tests/api/user/test_tasks.py

@@ -222,7 +222,7 @@ class TestSetupPeriodicTasks:
 
         setup_periodic_tasks(sender)
 
-        assert sender.add_periodic_task.call_count == 8
+        assert sender.add_periodic_task.call_count == 11
 
         calls = sender.add_periodic_task.call_args_list
 
@@ -246,6 +246,14 @@ class TestSetupPeriodicTasks:
         # message_events retention sweep (24h)
         assert calls[7][0][0] == timedelta(hours=24)
         assert calls[7][1].get("name") == "cleanup-message-events"
+        # orphan memories sweep (24h)
+        assert calls[8][0][0] == timedelta(hours=24)
+        assert calls[8][1].get("name") == "cleanup-orphan-memories"
+        # scheduler dispatcher
+        assert calls[9][1].get("name") == "dispatch-scheduled-runs"
+        # schedule runs cleanup (24h)
+        assert calls[10][0][0] == timedelta(hours=24)
+        assert calls[10][1].get("name") == "cleanup-schedule-runs"
 
 
 class TestMcpOauthTask:
@@ -296,6 +304,7 @@ class TestDurableTaskRetryPolicy:
             "cleanup_pending_tool_state",
             "reconciliation_task",
             "version_check_task",
+            "cleanup_orphan_memories",
         ],
     )
     def test_short_periodic_tasks_have_no_retry_config(self, task_name):
@@ -515,6 +524,72 @@ class TestCleanupMessageEventsTask:
         assert [r["sequence_no"] for r in rows] == [1]
 
 
+class TestCleanupOrphanMemoriesTask:
+    """Sweeps orphan memories from the FK-to-trigger orphan window."""
+
+    @pytest.mark.unit
+    def test_skips_when_postgres_uri_missing(self, monkeypatch):
+        from application.api.user.tasks import cleanup_orphan_memories
+        from application.core.settings import settings
+
+        monkeypatch.setattr(settings, "POSTGRES_URI", None, raising=False)
+
+        result = cleanup_orphan_memories.run()
+        assert result == {"deleted": 0, "skipped": "POSTGRES_URI not set"}
+
+    @pytest.mark.unit
+    def test_deletes_orphan_keeps_synthetic_and_live(
+        self, pg_conn, monkeypatch
+    ):
+        import uuid
+
+        from sqlalchemy import text as _text
+
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tasks import cleanup_orphan_memories
+        from application.core.settings import settings
+        from application.storage.db.repositories.memories import (
+            MemoriesRepository,
+        )
+
+        repo = MemoriesRepository(pg_conn)
+        synthetic_id = default_tool_id("memory")
+        live_id = str(
+            pg_conn.execute(
+                _text(
+                    "INSERT INTO user_tools (user_id, name) "
+                    "VALUES ('u-task-mem', 'memory') RETURNING id"
+                )
+            ).scalar()
+        )
+        orphan_id = str(uuid.uuid4())
+        repo.upsert("u-task-mem", synthetic_id, "/syn.txt", "keep")
+        repo.upsert("u-task-mem", live_id, "/live.txt", "keep")
+        repo.upsert("u-task-mem", orphan_id, "/orphan.txt", "drop")
+
+        monkeypatch.setattr(
+            settings, "POSTGRES_URI", "postgresql://stub", raising=False
+        )
+
+        @contextmanager
+        def _fake_begin():
+            yield pg_conn
+
+        fake_engine = MagicMock()
+        fake_engine.begin = _fake_begin
+
+        with patch(
+            "application.storage.db.engine.get_engine",
+            return_value=fake_engine,
+        ):
+            result = cleanup_orphan_memories.run()
+
+        assert result == {"deleted": 1}
+        assert repo.get_by_path("u-task-mem", synthetic_id, "/syn.txt")
+        assert repo.get_by_path("u-task-mem", live_id, "/live.txt")
+        assert repo.get_by_path("u-task-mem", orphan_id, "/orphan.txt") is None
+
+
 class TestIngestIdempotency:
     """Same short-circuit applies to the ingest task path."""
 

tests/api/user/test_tools_routes.py

@@ -1066,6 +1066,11 @@ def _seed_tool(pg_conn, user="u-tools", name="read_webpage", config=None):
 
 class TestGetToolsHappy:
     def test_returns_user_tools(self, app, pg_conn):
+        from application.agents.default_tools import (
+            BUILTIN_AGENT_TOOLS,
+            loaded_builtin_agent_tools,
+            loaded_default_tools,
+        )
         from application.api.user.tools.routes import GetTools
 
         user = "u-get-tools"
@@ -1079,7 +1084,26 @@ class TestGetToolsHappy:
             response = GetTools().get()
         assert response.status_code == 200
         assert response.json["success"] is True
-        assert len(response.json["tools"]) == 1
+        tools = response.json["tools"]
+        # Response shape: 1 explicit + every default + builtins not already
+        # surfaced as a default (dual-registered ``scheduler`` is dedup'd).
+        defaults_count = len(loaded_default_tools())
+        builtins_count = len(loaded_builtin_agent_tools())
+        dual = sum(
+            1 for name in loaded_default_tools() if name in BUILTIN_AGENT_TOOLS
+        )
+        assert len(tools) == 1 + defaults_count + (builtins_count - dual)
+        explicit = [
+            t for t in tools
+            if not t.get("default") and not t.get("builtin")
+        ]
+        defaults = [t for t in tools if t.get("default")]
+        builtins = [t for t in tools if t.get("builtin")]
+        assert len(explicit) == 1
+        assert len(defaults) == defaults_count
+        # Dual-registered tools (scheduler) appear once with both flags;
+        # ``builtins`` here counts them via ``builtin=True``.
+        assert len(builtins) == (builtins_count - dual) + dual
 
     def test_db_error_returns_400(self, app):
         from application.api.user.tools.routes import GetTools
@@ -1379,8 +1403,291 @@ class TestGetArtifactHappy:
         assert response.status_code == 404
 
 
+# ---------------------------------------------------------------------------
+# Default chat tools — synthetic-id branching in the tool endpoints
+# ---------------------------------------------------------------------------
+class TestDefaultToolsRoutes:
+    def test_get_tools_flags_defaults(self, app, pg_conn):
+        from application.agents.default_tools import (
+            default_tool_id,
+            loaded_default_tools,
+        )
+        from application.api.user.tools.routes import GetTools
+
+        user = "u-def-get"
+        with _patch_tools_db(pg_conn), app.test_request_context("/api/get_tools"):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = GetTools().get()
+        assert response.status_code == 200
+        defaults = [t for t in response.json["tools"] if t.get("default")]
+        names = {t["name"] for t in defaults}
+        assert names == set(loaded_default_tools())
+        for tool in defaults:
+            assert tool["id"] == default_tool_id(tool["name"])
+            assert tool["status"] is True
+
+    def test_get_tools_surfaces_scheduler_with_both_flags(self, app, pg_conn):
+        """Dual-registered scheduler appears once with default+builtin flags."""
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import GetTools
+
+        user = "u-sched-dual"
+        with _patch_tools_db(pg_conn), app.test_request_context("/api/get_tools"):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = GetTools().get()
+        assert response.status_code == 200
+        scheduler_id = default_tool_id("scheduler")
+        scheduler_rows = [
+            t for t in response.json["tools"] if t["id"] == scheduler_id
+        ]
+        assert len(scheduler_rows) == 1  # dedup at the routes layer
+        row = scheduler_rows[0]
+        assert row["default"] is True
+        assert row["builtin"] is True
+        assert row["name"] == "scheduler"
+
+    def test_get_tools_status_reflects_opt_out(self, app, pg_conn):
+        from application.api.user.tools.routes import GetTools
+        from application.storage.db.repositories.users import UsersRepository
+
+        user = "u-def-optout"
+        UsersRepository(pg_conn).set_default_tool_enabled(
+            user, "read_webpage", False
+        )
+        with _patch_tools_db(pg_conn), app.test_request_context("/api/get_tools"):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = GetTools().get()
+        by_name = {
+            t["name"]: t
+            for t in response.json["tools"]
+            if t.get("default")
+        }
+        assert by_name["read_webpage"]["status"] is False
+        assert by_name["memory"]["status"] is True
+
+    def test_update_tool_status_toggles_default_off(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateToolStatus
+        from application.storage.db.repositories.users import UsersRepository
+
+        user = "u-def-toggle"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool_status",
+            method="POST",
+            json={"id": default_tool_id("memory"), "status": False},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateToolStatus().post()
+        assert response.status_code == 200
+        user_doc = UsersRepository(pg_conn).get(user)
+        assert user_doc["tool_preferences"]["disabled_default_tools"] == ["memory"]
+
+    def test_update_tool_status_toggles_default_back_on(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateToolStatus
+        from application.storage.db.repositories.users import UsersRepository
+
+        user = "u-def-on"
+        UsersRepository(pg_conn).set_default_tool_enabled(user, "memory", False)
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool_status",
+            method="POST",
+            json={"id": default_tool_id("memory"), "status": True},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateToolStatus().post()
+        assert response.status_code == 200
+        user_doc = UsersRepository(pg_conn).get(user)
+        assert user_doc["tool_preferences"]["disabled_default_tools"] == []
+
+    def test_update_tool_toggles_default_via_status(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateTool
+        from application.storage.db.repositories.users import UsersRepository
+
+        user = "u-def-updtool"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool",
+            method="POST",
+            json={"id": default_tool_id("read_webpage"), "status": False},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateTool().post()
+        assert response.status_code == 200
+        user_doc = UsersRepository(pg_conn).get(user)
+        assert user_doc["tool_preferences"]["disabled_default_tools"] == [
+            "read_webpage"
+        ]
+
+    def test_delete_tool_rejects_default(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import DeleteTool
+
+        user = "u-def-del"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/delete_tool",
+            method="POST",
+            json={"id": default_tool_id("memory")},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = DeleteTool().post()
+        assert response.status_code == 400
+        assert response.json["success"] is False
+
+    def test_update_tool_default_without_status_is_rejected(
+        self, app, pg_conn
+    ):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateTool
+
+        user = "u-def-noedit"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool",
+            method="POST",
+            json={"id": default_tool_id("memory"), "displayName": "Renamed"},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateTool().post()
+        assert response.status_code == 400
+        assert response.json["success"] is False
+        assert "not editable" in response.json["message"]
+
+    def test_update_tool_config_rejects_default(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateToolConfig
+
+        user = "u-def-cfg"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool_config",
+            method="POST",
+            json={"id": default_tool_id("memory"), "config": {"x": 1}},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateToolConfig().post()
+        assert response.status_code == 400
+        assert response.json["success"] is False
+        assert "config-free" in response.json["message"]
+
+    def test_update_tool_actions_rejects_default(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateToolActions
+
+        user = "u-def-act"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool_actions",
+            method="POST",
+            json={"id": default_tool_id("memory"), "actions": []},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateToolActions().post()
+        assert response.status_code == 400
+        assert response.json["success"] is False
+        assert "not editable" in response.json["message"]
 
 
+# ---------------------------------------------------------------------------
+# Dual-registered tools (scheduler) — toggle MUST hit the default-tool path,
+# not the builtin "not editable" rejection. Regression for the iter-6 issue
+# where ``is_builtin_agent_tool_id`` was checked first, silently dropping the
+# write on a dual-registered uuid5.
+# ---------------------------------------------------------------------------
+class TestDualRegisteredToggle:
+    def test_update_tool_status_off_writes_disabled_default(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateToolStatus
+        from application.storage.db.repositories.users import UsersRepository
 
+        user = "u-sched-off"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool_status",
+            method="POST",
+            json={"id": default_tool_id("scheduler"), "status": False},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateToolStatus().post()
+        assert response.status_code == 200
+        assert response.json["success"] is True
+        user_doc = UsersRepository(pg_conn).get(user)
+        assert "scheduler" in (
+            user_doc["tool_preferences"]["disabled_default_tools"]
+        )
+
+    def test_update_tool_status_on_removes_disabled_default(self, app, pg_conn):
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateToolStatus
+        from application.storage.db.repositories.users import UsersRepository
+
+        user = "u-sched-on"
+        UsersRepository(pg_conn).set_default_tool_enabled(
+            user, "scheduler", False,
+        )
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool_status",
+            method="POST",
+            json={"id": default_tool_id("scheduler"), "status": True},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateToolStatus().post()
+        assert response.status_code == 200
+        assert response.json["success"] is True
+        user_doc = UsersRepository(pg_conn).get(user)
+        assert "scheduler" not in (
+            user_doc["tool_preferences"]["disabled_default_tools"]
+        )
+
+    def test_update_tool_status_round_trip(self, app, pg_conn):
+        """Off → on returns to the empty-list baseline."""
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateToolStatus
+        from application.storage.db.repositories.users import UsersRepository
+
+        user = "u-sched-rt"
+        scheduler_id = default_tool_id("scheduler")
+        for status in (False, True):
+            with _patch_tools_db(pg_conn), app.test_request_context(
+                "/api/update_tool_status",
+                method="POST",
+                json={"id": scheduler_id, "status": status},
+            ):
+                from flask import request
+                request.decoded_token = {"sub": user}
+                response = UpdateToolStatus().post()
+            assert response.status_code == 200
+        user_doc = UsersRepository(pg_conn).get(user)
+        assert user_doc["tool_preferences"]["disabled_default_tools"] == []
+
+    def test_update_tool_with_status_writes_disabled_default(self, app, pg_conn):
+        """The /api/update_tool route also honours the default branch first."""
+        from application.agents.default_tools import default_tool_id
+        from application.api.user.tools.routes import UpdateTool
+        from application.storage.db.repositories.users import UsersRepository
+
+        user = "u-sched-upd"
+        with _patch_tools_db(pg_conn), app.test_request_context(
+            "/api/update_tool",
+            method="POST",
+            json={"id": default_tool_id("scheduler"), "status": False},
+        ):
+            from flask import request
+            request.decoded_token = {"sub": user}
+            response = UpdateTool().post()
+        assert response.status_code == 200
+        assert response.json["success"] is True
+        user_doc = UsersRepository(pg_conn).get(user)
+        assert "scheduler" in (
+            user_doc["tool_preferences"]["disabled_default_tools"]
+        )