diff --git a/nanobot/cli/commands.py b/nanobot/cli/commands.py
index ca26cbf37..29eb19c31 100644
--- a/nanobot/cli/commands.py
+++ b/nanobot/cli/commands.py
@@ -1,12 +1,11 @@
 """CLI commands for nanobot."""
 
 import asyncio
-from contextlib import contextmanager, nullcontext
-
 import os
 import select
 import signal
 import sys
+from contextlib import nullcontext
 from pathlib import Path
 from typing import Any
 
@@ -73,6 +72,7 @@ def _flush_pending_tty_input() -> None:
 
     try:
         import termios
+
         termios.tcflush(fd, termios.TCIFLUSH)
         return
     except Exception:
@@ -95,6 +95,7 @@ def _restore_terminal() -> None:
         return
     try:
         import termios
+
         termios.tcsetattr(sys.stdin.fileno(), termios.TCSADRAIN, _SAVED_TERM_ATTRS)
     except Exception:
         pass
@@ -107,6 +108,7 @@ def _init_prompt_session() -> None:
     # Save terminal state so we can restore it on exit
     try:
         import termios
+
         _SAVED_TERM_ATTRS = termios.tcgetattr(sys.stdin.fileno())
     except Exception:
         pass
@@ -119,7 +121,7 @@ def _init_prompt_session() -> None:
     _PROMPT_SESSION = PromptSession(
         history=FileHistory(str(history_file)),
         enable_open_in_editor=False,
-        multiline=False,   # Enter submits (single line mode)
+        multiline=False,  # Enter submits (single line mode)
     )
 
 
@@ -231,7 +233,6 @@ async def _read_interactive_input_async() -> str:
         raise KeyboardInterrupt from exc
 
 
-
 def version_callback(value: bool):
     if value:
         console.print(f"{__logo__} nanobot v{__version__}")
@@ -281,8 +282,12 @@ def onboard(
             config = _apply_workspace_override(load_config(config_path))
         else:
             console.print(f"[yellow]Config already exists at {config_path}[/yellow]")
-            console.print("  [bold]y[/bold] = overwrite with defaults (existing values will be lost)")
-            console.print("  [bold]N[/bold] = refresh config, keeping existing values and adding new fields")
+            console.print(
+                "  [bold]y[/bold] = overwrite with defaults (existing values will be lost)"
+            )
+            console.print(
+                "  [bold]N[/bold] = refresh config, keeping existing values and adding new fields"
+            )
             if typer.confirm("Overwrite?"):
                 config = _apply_workspace_override(Config())
                 save_config(config, config_path)
@@ -290,7 +295,9 @@ def onboard(
             else:
                 config = _apply_workspace_override(load_config(config_path))
                 save_config(config, config_path)
-                console.print(f"[green]✓[/green] Config refreshed at {config_path} (existing values preserved)")
+                console.print(
+                    f"[green]✓[/green] Config refreshed at {config_path} (existing values preserved)"
+                )
     else:
         config = _apply_workspace_override(Config())
         # In wizard mode, don't save yet - the wizard will handle saving if should_save=True
@@ -340,7 +347,9 @@ def onboard(
         console.print(f"  1. Add your API key to [cyan]{config_path}[/cyan]")
         console.print("     Get one at: https://openrouter.ai/keys")
         console.print(f"  2. Chat: [cyan]{agent_cmd}[/cyan]")
-    console.print("\n[dim]Want Telegram/WhatsApp? See: https://github.com/HKUDS/nanobot#-chat-apps[/dim]")
+    console.print(
+        "\n[dim]Want Telegram/WhatsApp? See: https://github.com/HKUDS/nanobot#-chat-apps[/dim]"
+    )
 
 
 def _merge_missing_defaults(existing: Any, defaults: Any) -> Any:
@@ -413,9 +422,11 @@ def _make_provider(config: Config):
     # --- instantiation by backend ---
     if backend == "openai_codex":
         from nanobot.providers.openai_codex_provider import OpenAICodexProvider
+
         provider = OpenAICodexProvider(default_model=model)
     elif backend == "azure_openai":
         from nanobot.providers.azure_openai_provider import AzureOpenAIProvider
+
         provider = AzureOpenAIProvider(
             api_key=p.api_key,
             api_base=p.api_base,
@@ -426,6 +437,7 @@ def _make_provider(config: Config):
         provider = GitHubCopilotProvider(default_model=model)
     elif backend == "anthropic":
         from nanobot.providers.anthropic_provider import AnthropicProvider
+
         provider = AnthropicProvider(
             api_key=p.api_key if p else None,
             api_base=config.get_api_base(model),
@@ -434,6 +446,7 @@ def _make_provider(config: Config):
         )
     else:
         from nanobot.providers.openai_compat_provider import OpenAICompatProvider
+
         provider = OpenAICompatProvider(
             api_key=p.api_key if p else None,
             api_base=config.get_api_base(model),
@@ -478,6 +491,7 @@ def _load_runtime_config(config: str | None = None, workspace: str | None = None
 def _warn_deprecated_config_keys(config_path: Path | None) -> None:
     """Hint users to remove obsolete keys from their config file."""
     import json
+
     from nanobot.config.loader import get_config_path
 
     path = config_path or get_config_path()
@@ -501,6 +515,7 @@ def _migrate_cron_store(config: "Config") -> None:
     if legacy_path.is_file() and not new_path.exists():
         new_path.parent.mkdir(parents=True, exist_ok=True)
         import shutil
+
         shutil.move(str(legacy_path), str(new_path))
 
 
@@ -614,6 +629,7 @@ def gateway(
 
     if verbose:
         import logging
+
         logging.basicConfig(level=logging.DEBUG)
 
     config = _load_runtime_config(config, workspace)
@@ -699,7 +715,7 @@ def gateway(
 
         if job.payload.deliver and job.payload.to and response:
             should_notify = await evaluate_response(
-                response, job.payload.message, provider, agent.model,
+                response, reminder_note, provider, agent.model,
             )
             if should_notify:
                 from nanobot.bus.events import OutboundMessage
@@ -709,6 +725,7 @@ def gateway(
                     content=response,
                 ))
         return response
+
     cron.on_job = on_cron_job
 
     # Create channel manager
@@ -812,6 +829,7 @@ def gateway(
             console.print("\nShutting down...")
         except Exception:
             import traceback
+
             console.print("\n[red]Error: Gateway crashed unexpectedly[/red]")
             console.print(traceback.format_exc())
         finally:
@@ -824,8 +842,6 @@ def gateway(
     asyncio.run(run())
 
 
-
-
 # ============================================================================
 # Agent Commands
 # ============================================================================
@@ -1300,6 +1316,7 @@ def _register_login(name: str):
     def decorator(fn):
         _LOGIN_HANDLERS[name] = fn
         return fn
+
     return decorator
 
 
@@ -1330,6 +1347,7 @@ def provider_login(
 def _login_openai_codex() -> None:
     try:
         from oauth_cli_kit import get_token, login_oauth_interactive
+
         token = None
         try:
             token = get_token()
diff --git a/nanobot/templates/agent/evaluator.md b/nanobot/templates/agent/evaluator.md
index 305e4f8d0..51cf7a4e4 100644
--- a/nanobot/templates/agent/evaluator.md
+++ b/nanobot/templates/agent/evaluator.md
@@ -1,7 +1,9 @@
 {% if part == 'system' %}
 You are a notification gate for a background agent. You will be given the original task and the agent's response. Call the evaluate_notification tool to decide whether the user should be notified.
 
-Notify when the response contains actionable information, errors, completed deliverables, or anything the user explicitly asked to be reminded about.
+Notify when the response contains actionable information, errors, completed deliverables, scheduled reminder/timer completions, or anything the user explicitly asked to be reminded about.
+
+A user-scheduled reminder should usually notify even when the response is brief or mostly repeats the original reminder.
 
 Suppress when the response is a routine status check with nothing new, a confirmation that everything is normal, or essentially empty.
 {% elif part == 'user' %}
diff --git a/tests/cli/test_commands.py b/tests/cli/test_commands.py
index 4a1a00632..3a1e7145a 100644
--- a/tests/cli/test_commands.py
+++ b/tests/cli/test_commands.py
@@ -1,5 +1,7 @@
+import asyncio
 import json
 import re
+import shutil
 from pathlib import Path
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -9,6 +11,7 @@ from typer.testing import CliRunner
 from nanobot.bus.events import OutboundMessage
 from nanobot.cli.commands import _make_provider, app
 from nanobot.config.schema import Config
+from nanobot.cron.types import CronJob, CronPayload
 from nanobot.providers.openai_codex_provider import _strip_model_prefix
 from nanobot.providers.registry import find_by_name
 
@@ -19,11 +22,6 @@ class _StopGatewayError(RuntimeError):
     pass
 
 
-import shutil
-
-import pytest
-
-
 @pytest.fixture
 def mock_paths():
     """Mock config/workspace paths for test isolation."""
@@ -31,7 +29,6 @@ def mock_paths():
          patch("nanobot.config.loader.save_config") as mock_sc, \
          patch("nanobot.config.loader.load_config") as mock_lc, \
          patch("nanobot.cli.commands.get_workspace_path") as mock_ws:
-
         base_dir = Path("./test_onboard_data")
         if base_dir.exists():
             shutil.rmtree(base_dir)
@@ -432,7 +429,6 @@ def mock_agent_runtime(tmp_path):
          patch("nanobot.bus.queue.MessageBus"), \
          patch("nanobot.cron.service.CronService"), \
          patch("nanobot.agent.loop.AgentLoop") as mock_agent_loop_cls:
-
         agent_loop = MagicMock()
         agent_loop.channels_config = None
         agent_loop.process_direct = AsyncMock(
@@ -657,7 +653,9 @@ def test_agent_custom_config_workspace_does_not_migrate_legacy_cron(
 
     monkeypatch.setattr("nanobot.cron.service.CronService", _FakeCron)
     monkeypatch.setattr("nanobot.agent.loop.AgentLoop", _FakeAgentLoop)
-    monkeypatch.setattr("nanobot.cli.commands._print_agent_response", lambda *_args, **_kwargs: None)
+    monkeypatch.setattr(
+        "nanobot.cli.commands._print_agent_response", lambda *_args, **_kwargs: None
+    )
 
     result = runner.invoke(app, ["agent", "-m", "hello", "-c", str(config_file)])
 
@@ -870,6 +868,115 @@ def test_gateway_uses_workspace_directory_for_cron_store(monkeypatch, tmp_path:
     assert seen["cron_store"] == config.workspace_path / "cron" / "jobs.json"
 
 
+def test_gateway_cron_evaluator_receives_scheduled_reminder_context(
+    monkeypatch, tmp_path: Path
+) -> None:
+    config_file = tmp_path / "instance" / "config.json"
+    config_file.parent.mkdir(parents=True)
+    config_file.write_text("{}")
+
+    config = Config()
+    config.agents.defaults.workspace = str(tmp_path / "config-workspace")
+    provider = object()
+    bus = MagicMock()
+    bus.publish_outbound = AsyncMock()
+    seen: dict[str, object] = {}
+
+    monkeypatch.setattr("nanobot.config.loader.set_config_path", lambda _path: None)
+    monkeypatch.setattr("nanobot.config.loader.load_config", lambda _path=None: config)
+    monkeypatch.setattr("nanobot.cli.commands.sync_workspace_templates", lambda _path: None)
+    monkeypatch.setattr("nanobot.cli.commands._make_provider", lambda _config: provider)
+    monkeypatch.setattr("nanobot.bus.queue.MessageBus", lambda: bus)
+    monkeypatch.setattr("nanobot.session.manager.SessionManager", lambda _workspace: object())
+
+    class _FakeCron:
+        def __init__(self, _store_path: Path) -> None:
+            self.on_job = None
+            seen["cron"] = self
+
+    class _FakeAgentLoop:
+        def __init__(self, *args, **kwargs) -> None:
+            self.model = "test-model"
+            self.tools = {}
+
+        async def process_direct(self, *_args, **_kwargs):
+            return OutboundMessage(
+                channel="telegram",
+                chat_id="user-1",
+                content="Time to stretch.",
+            )
+
+        async def close_mcp(self) -> None:
+            return None
+
+        async def run(self) -> None:
+            return None
+
+        def stop(self) -> None:
+            return None
+
+    class _StopAfterCronSetup:
+        def __init__(self, *_args, **_kwargs) -> None:
+            raise _StopGatewayError("stop")
+
+    async def _capture_evaluate_response(
+        response: str,
+        task_context: str,
+        provider_arg: object,
+        model: str,
+    ) -> bool:
+        seen["response"] = response
+        seen["task_context"] = task_context
+        seen["provider"] = provider_arg
+        seen["model"] = model
+        return True
+
+    monkeypatch.setattr("nanobot.cron.service.CronService", _FakeCron)
+    monkeypatch.setattr("nanobot.agent.loop.AgentLoop", _FakeAgentLoop)
+    monkeypatch.setattr("nanobot.channels.manager.ChannelManager", _StopAfterCronSetup)
+    monkeypatch.setattr(
+        "nanobot.utils.evaluator.evaluate_response",
+        _capture_evaluate_response,
+    )
+
+    result = runner.invoke(app, ["gateway", "--config", str(config_file)])
+
+    assert isinstance(result.exception, _StopGatewayError)
+    cron = seen["cron"]
+    assert isinstance(cron, _FakeCron)
+    assert cron.on_job is not None
+
+    job = CronJob(
+        id="cron-1",
+        name="stretch",
+        payload=CronPayload(
+            message="Remind me to stretch.",
+            deliver=True,
+            channel="telegram",
+            to="user-1",
+        ),
+    )
+
+    response = asyncio.run(cron.on_job(job))
+
+    assert response == "Time to stretch."
+    assert seen["response"] == "Time to stretch."
+    assert seen["provider"] is provider
+    assert seen["model"] == "test-model"
+    assert seen["task_context"] == (
+        "[Scheduled Task] Timer finished.\n\n"
+        "Task 'stretch' has been triggered.\n"
+        "Scheduled instruction: Remind me to stretch."
+    )
+    bus.publish_outbound.assert_awaited_once_with(
+        OutboundMessage(
+            channel="telegram",
+            chat_id="user-1",
+            content="Time to stretch.",
+        )
+    )
+
+
 def test_gateway_workspace_override_does_not_migrate_legacy_cron(
     monkeypatch, tmp_path: Path
 ) -> None: