diff --git a/nanobot/agent/cron_turns.py b/nanobot/agent/cron_turns.py
index da456ba48..a589338c3 100644
--- a/nanobot/agent/cron_turns.py
+++ b/nanobot/agent/cron_turns.py
@@ -7,7 +7,11 @@ import dataclasses
 from collections.abc import Awaitable, Callable, Iterable
 
 from nanobot.bus.events import InboundMessage, OutboundMessage
-from nanobot.cron.session_turns import cron_run_id, defer_cron_until_session_idle
+from nanobot.cron.session_turns import (
+    cron_run_id,
+    cron_trigger,
+    defer_cron_until_session_idle,
+)
 
 
 class CronTurnCoordinator:
@@ -25,6 +29,7 @@ class CronTurnCoordinator:
         self._is_running = is_running
         self.deferred_queues: dict[str, list[InboundMessage]] = {}
         self._waiters: dict[str, asyncio.Future[OutboundMessage | None]] = {}
+        self._pending_messages_by_run_id: dict[str, InboundMessage] = {}
 
     async def submit(self, msg: InboundMessage) -> OutboundMessage | None:
         """Submit a scheduled cron turn and wait for its session response."""
@@ -37,6 +42,7 @@ class CronTurnCoordinator:
         loop = asyncio.get_running_loop()
         future: asyncio.Future[OutboundMessage | None] = loop.create_future()
         self._waiters[run_id] = future
+        self._pending_messages_by_run_id[run_id] = msg
         try:
             if self._is_running():
                 await self._publish_inbound(msg)
@@ -45,6 +51,7 @@ class CronTurnCoordinator:
             return await future
         finally:
             self._waiters.pop(run_id, None)
+            self._pending_messages_by_run_id.pop(run_id, None)
 
     def should_defer(
         self,
@@ -102,6 +109,21 @@ class CronTurnCoordinator:
     def defer(self, session_key: str, msg: InboundMessage) -> None:
         self.deferred_queues.setdefault(session_key, []).append(msg)
 
+    def pending_job_ids_for_session(self, session_key: str) -> set[str]:
+        """Return cron jobs that are waiting for or running in *session_key*."""
+        job_ids: set[str] = set()
+        for msg in self.deferred_queues.get(session_key, []):
+            job_id = _cron_job_id(msg)
+            if job_id:
+                job_ids.add(job_id)
+        for msg in self._pending_messages_by_run_id.values():
+            if msg.session_key != session_key:
+                continue
+            job_id = _cron_job_id(msg)
+            if job_id:
+                job_ids.add(job_id)
+        return job_ids
+
     async def publish_next_deferred(self, session_key: str) -> None:
         queue = self.deferred_queues.get(session_key)
         if not queue:
@@ -110,3 +132,11 @@ class CronTurnCoordinator:
         if not queue:
             self.deferred_queues.pop(session_key, None)
         await self._publish_inbound(msg)
+
+
+def _cron_job_id(msg: InboundMessage) -> str | None:
+    trigger = cron_trigger(msg.metadata)
+    if not trigger:
+        return None
+    value = trigger.get("job_id")
+    return value if isinstance(value, str) and value else None
diff --git a/nanobot/agent/loop.py b/nanobot/agent/loop.py
index 576848139..ad57dc875 100644
--- a/nanobot/agent/loop.py
+++ b/nanobot/agent/loop.py
@@ -574,6 +574,9 @@ class AgentLoop:
     async def submit_cron_turn(self, msg: InboundMessage) -> OutboundMessage | None:
         return await self._cron_turns.submit(msg)
 
+    def pending_cron_job_ids_for_session(self, session_key: str) -> set[str]:
+        return self._cron_turns.pending_job_ids_for_session(session_key)
+
     def _persist_user_message_early(
         self,
         msg: InboundMessage,
diff --git a/nanobot/channels/manager.py b/nanobot/channels/manager.py
index b59925232..a28ebdcba 100644
--- a/nanobot/channels/manager.py
+++ b/nanobot/channels/manager.py
@@ -58,6 +58,7 @@ class ChannelManager:
         session_manager: "SessionManager | None" = None,
         cron_service: Any | None = None,
         webui_runtime_model_name: Callable[[], str | None] | None = None,
+        webui_cron_pending_job_ids: Callable[[str], set[str]] | None = None,
         webui_static_dist: bool = True,
         webui_runtime_surface: str = "browser",
         webui_runtime_capabilities: dict[str, Any] | None = None,
@@ -67,6 +68,7 @@ class ChannelManager:
         self._session_manager = session_manager
         self._cron_service = cron_service
         self._webui_runtime_model_name = webui_runtime_model_name
+        self._webui_cron_pending_job_ids = webui_cron_pending_job_ids
         self._webui_static_dist = webui_static_dist
         self._webui_runtime_surface = webui_runtime_surface
         self._webui_runtime_capabilities = dict(webui_runtime_capabilities or {})
@@ -126,6 +128,7 @@ class ChannelManager:
                         runtime_surface=self._webui_runtime_surface,
                         runtime_capabilities_overrides=self._webui_runtime_capabilities,
                         cron_service=self._cron_service,
+                        cron_pending_job_ids=self._webui_cron_pending_job_ids,
                         logger=logger,
                     )
                     kwargs["gateway"] = gateway
diff --git a/nanobot/cli/commands.py b/nanobot/cli/commands.py
index bd40dd2aa..a1baf101b 100644
--- a/nanobot/cli/commands.py
+++ b/nanobot/cli/commands.py
@@ -947,7 +947,7 @@ def _run_gateway(
     from nanobot.bus.runtime_events import RuntimeEventBus
     from nanobot.channels.manager import ChannelManager
     from nanobot.cron.bound_runner import run_bound_cron_job
-    from nanobot.cron.service import CronService
+    from nanobot.cron.service import CronJobSkippedError, CronService
     from nanobot.cron.session_turns import is_bound_cron_job
     from nanobot.cron.types import CronJob
     from nanobot.providers.factory import build_provider_snapshot, load_provider_snapshot
@@ -1167,12 +1167,14 @@ def _run_gateway(
         if is_bound_cron_job(job):
             return await run_bound_cron_job(job, agent=agent, cron=cron)
 
+        reason = "unbound agent cron job must be recreated from a chat session"
         logger.warning(
-            "Cron: skipped unbound agent job '{}' ({}); recreate it from a chat session",
+            "Cron: skipped unbound agent job '{}' ({}): {}",
             job.name,
             job.id,
+            reason,
         )
-        return None
+        raise CronJobSkippedError(reason)
 
     cron.on_job = on_cron_job
 
@@ -1191,6 +1193,7 @@ def _run_gateway(
         session_manager=session_manager,
         cron_service=cron,
         webui_runtime_model_name=_webui_runtime_model_name,
+        webui_cron_pending_job_ids=getattr(agent, "pending_cron_job_ids_for_session", None),
         webui_static_dist=webui_static_dist,
         webui_runtime_surface=webui_runtime_surface,
         webui_runtime_capabilities=webui_runtime_capabilities,
diff --git a/nanobot/cron/service.py b/nanobot/cron/service.py
index 1a66af007..16fab16b4 100644
--- a/nanobot/cron/service.py
+++ b/nanobot/cron/service.py
@@ -25,6 +25,10 @@ from nanobot.cron.types import (
 )
 
 
+class CronJobSkippedError(Exception):
+    """Raised by cron callbacks when a job was intentionally skipped."""
+
+
 def _now_ms() -> int:
     return int(time.time() * 1000)
 
@@ -524,6 +528,10 @@ class CronService:
             job.state.last_error = None
             logger.info("Cron: job '{}' completed", job.name)
 
+        except CronJobSkippedError as e:
+            job.state.last_status = "skipped"
+            job.state.last_error = str(e) or None
+            logger.warning("Cron: job '{}' skipped: {}", job.name, job.state.last_error or "")
         except asyncio.CancelledError as e:
             current = asyncio.current_task()
             if current is not None and current.cancelling():
diff --git a/nanobot/utils/evaluator.py b/nanobot/utils/evaluator.py
index 89759523a..07206f991 100644
--- a/nanobot/utils/evaluator.py
+++ b/nanobot/utils/evaluator.py
@@ -1,6 +1,6 @@
-"""Post-run evaluation for background tasks (heartbeat & cron).
+"""Post-run notification evaluation for heartbeat checks.
 
-After the agent executes a background task, this module makes a lightweight
+After heartbeat executes an internal check, this module makes a lightweight
 LLM call to decide whether the result warrants notifying the user.
 """
 
@@ -46,10 +46,10 @@ async def evaluate_response(
     model: str,
     default_notify: bool = True,
 ) -> bool:
-    """Decide whether a background-task result should be delivered to the user.
+    """Decide whether a heartbeat result should be delivered to the user.
 
-    On any failure, falls back to ``default_notify`` (cron reminders fail open;
-    heartbeat passes ``False`` to fail closed).
+    On any failure, falls back to ``default_notify``. Heartbeat passes
+    ``False`` to fail closed.
     """
     try:
         llm_response = await provider.chat_with_retry(
diff --git a/nanobot/webui/gateway_services.py b/nanobot/webui/gateway_services.py
index 15649d08d..fa94b8f67 100644
--- a/nanobot/webui/gateway_services.py
+++ b/nanobot/webui/gateway_services.py
@@ -4,7 +4,7 @@ from __future__ import annotations
 
 from dataclasses import dataclass
 from pathlib import Path
-from typing import Any
+from typing import Any, Callable
 
 from loguru import logger as default_logger
 
@@ -26,6 +26,7 @@ class GatewayServices:
     workspaces: WebUIWorkspaceController
     session_manager: Any | None
     cron_service: Any | None
+    cron_pending_job_ids: Callable[[str], set[str]] | None
 
 
 def build_gateway_services(
@@ -41,6 +42,7 @@ def build_gateway_services(
     runtime_capabilities_overrides: dict[str, Any] | None,
     disabled_skills: set[str] | None = None,
     cron_service: Any | None = None,
+    cron_pending_job_ids: Callable[[str], set[str]] | None = None,
     logger: Any = default_logger,
 ) -> GatewayServices:
     tokens = GatewayTokenStore()
@@ -68,6 +70,7 @@ def build_gateway_services(
         skills_workspace_path=workspace_path,
         disabled_skills=disabled_skills,
         cron_service=cron_service,
+        cron_pending_job_ids=cron_pending_job_ids,
         log=logger,
     )
     return GatewayServices(
@@ -78,4 +81,5 @@ def build_gateway_services(
         workspaces=workspaces,
         session_manager=session_manager,
         cron_service=cron_service,
+        cron_pending_job_ids=cron_pending_job_ids,
     )
diff --git a/nanobot/webui/session_automations.py b/nanobot/webui/session_automations.py
index 3eb56e5b2..c87dfd094 100644
--- a/nanobot/webui/session_automations.py
+++ b/nanobot/webui/session_automations.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+from collections.abc import Collection
 from typing import Any, Protocol
 
 from nanobot.cron.types import CronJob
@@ -32,18 +33,27 @@ def session_automation_jobs(
 def session_automations_payload(
     cron_service: _CronServiceLike | None,
     session_key: str,
+    *,
+    pending_job_ids: Collection[str] | None = None,
 ) -> dict[str, Any]:
     """Return user-created automation jobs attached to a WebUI session."""
     return {
-        "jobs": serialize_automation_jobs(session_automation_jobs(cron_service, session_key))
+        "jobs": serialize_automation_jobs(
+            session_automation_jobs(cron_service, session_key),
+            pending_job_ids=pending_job_ids,
+        )
     }
 
 
-def serialize_automation_jobs(jobs: list[CronJob]) -> list[dict[str, Any]]:
-    return [_serialize_job(job) for job in jobs]
+def serialize_automation_jobs(
+    jobs: list[CronJob],
+    *,
+    pending_job_ids: Collection[str] | None = None,
+) -> list[dict[str, Any]]:
+    return [_serialize_job(job, pending=job.id in (pending_job_ids or ())) for job in jobs]
 
 
-def _serialize_job(job: CronJob) -> dict[str, Any]:
+def _serialize_job(job: CronJob, *, pending: bool = False) -> dict[str, Any]:
     return {
         "id": job.id,
         "name": job.name,
@@ -61,5 +71,6 @@ def _serialize_job(job: CronJob) -> dict[str, Any]:
         "state": {
             "next_run_at_ms": job.state.next_run_at_ms,
             "last_status": job.state.last_status,
+            "pending": pending,
         },
     }
diff --git a/nanobot/webui/ws_http.py b/nanobot/webui/ws_http.py
index 70e19e01b..2ccdedac4 100644
--- a/nanobot/webui/ws_http.py
+++ b/nanobot/webui/ws_http.py
@@ -146,6 +146,7 @@ class GatewayHTTPHandler:
         skills_workspace_path: Path,
         disabled_skills: set[str] | None = None,
         cron_service: CronService | None = None,
+        cron_pending_job_ids: Callable[[str], set[str]] | None = None,
         log: Any = logger,
     ) -> None:
         self.config = config
@@ -159,6 +160,7 @@ class GatewayHTTPHandler:
         self.skills_workspace_path = skills_workspace_path
         self.disabled_skills = disabled_skills or set()
         self.cron_service = cron_service
+        self.cron_pending_job_ids = cron_pending_job_ids
         self._log = log
         self._runtime_surface = runtime_surface
 
@@ -436,8 +438,15 @@ class GatewayHTTPHandler:
             return _http_error(400, "invalid session key")
         if not _is_websocket_channel_session_key(decoded_key):
             return _http_error(404, "session not found")
+        pending_job_ids: set[str] = set()
+        if self.cron_pending_job_ids is not None:
+            pending_job_ids = self.cron_pending_job_ids(decoded_key)
         return _http_json_response(
-            session_automations_payload(self.cron_service, decoded_key)
+            session_automations_payload(
+                self.cron_service,
+                decoded_key,
+                pending_job_ids=pending_job_ids,
+            )
         )
 
     def _handle_session_delete(self, request: WsRequest, key: str) -> Response:
diff --git a/tests/agent/test_evaluator.py b/tests/agent/test_evaluator.py
index 62da88d66..acefe40e1 100644
--- a/tests/agent/test_evaluator.py
+++ b/tests/agent/test_evaluator.py
@@ -1,7 +1,7 @@
 import pytest
 
-from nanobot.utils.evaluator import evaluate_response
 from nanobot.providers.base import LLMProvider, LLMResponse, ToolCallRequest
+from nanobot.utils.evaluator import evaluate_response
 
 
 class DummyProvider(LLMProvider):
diff --git a/tests/agent/test_runner_injections.py b/tests/agent/test_runner_injections.py
index 97d653f3a..3b94569d9 100644
--- a/tests/agent/test_runner_injections.py
+++ b/tests/agent/test_runner_injections.py
@@ -639,7 +639,7 @@ async def test_cron_turn_deferred_while_session_active(tmp_path):
         chat_id="chat-1",
         content="scheduled work",
         metadata={
-            CRON_TRIGGER_META: {"run_id": "run-1"},
+            CRON_TRIGGER_META: {"job_id": "job-1", "run_id": "run-1"},
             CRON_DEFER_UNTIL_IDLE_META: True,
         },
         session_key_override=session_key,
@@ -657,11 +657,49 @@ async def test_cron_turn_deferred_while_session_active(tmp_path):
     assert pending.empty()
     assert loop._dispatch.await_count == 0
     assert loop._cron_turns.deferred_queues[session_key] == [msg]
+    assert loop.pending_cron_job_ids_for_session(session_key) == {"job-1"}
 
     await loop._cron_turns.publish_next_deferred(session_key)
     queued = await asyncio.wait_for(loop.bus.consume_inbound(), timeout=0.5)
     assert queued is msg
     assert session_key not in loop._cron_turns.deferred_queues
+    assert loop.pending_cron_job_ids_for_session(session_key) == set()
+
+
+@pytest.mark.asyncio
+async def test_submitted_cron_turn_reports_pending_until_completed(tmp_path):
+    """Bound cron jobs remain marked pending while their session turn is in flight."""
+    from nanobot.bus.events import InboundMessage, OutboundMessage
+    from nanobot.cron.session_turns import CRON_TRIGGER_META
+
+    loop = _make_loop(tmp_path)
+    loop._running = True
+
+    session_key = "websocket:chat-1"
+    msg = InboundMessage(
+        channel="websocket",
+        sender_id="cron",
+        chat_id="chat-1",
+        content="scheduled work",
+        metadata={CRON_TRIGGER_META: {"job_id": "job-1", "run_id": "run-1"}},
+        session_key_override=session_key,
+    )
+
+    submit_task = asyncio.create_task(loop.submit_cron_turn(msg))
+    queued = await asyncio.wait_for(loop.bus.consume_inbound(), timeout=0.5)
+
+    assert queued is msg
+    assert loop.pending_cron_job_ids_for_session(session_key) == {"job-1"}
+
+    response = OutboundMessage(
+        channel="websocket",
+        chat_id="chat-1",
+        content="done",
+    )
+    loop._cron_turns.complete(msg, response=response)
+
+    assert await asyncio.wait_for(submit_task, timeout=0.5) is response
+    assert loop.pending_cron_job_ids_for_session(session_key) == set()
 
 
 @pytest.mark.asyncio
diff --git a/tests/channels/test_websocket_http_routes.py b/tests/channels/test_websocket_http_routes.py
index c364f5a36..63dba4861 100644
--- a/tests/channels/test_websocket_http_routes.py
+++ b/tests/channels/test_websocket_http_routes.py
@@ -30,6 +30,7 @@ def _make_handler(
     workspace_path: Path | None = None,
     runtime_model_name: Any | None = None,
     cron_service: CronService | None = None,
+    cron_pending_job_ids: Any | None = None,
 ) -> GatewayServices:
     config = WebSocketConfig.model_validate(cfg) if isinstance(cfg, dict) else cfg
     workspace = workspace_path or Path.cwd()
@@ -44,6 +45,7 @@ def _make_handler(
         runtime_surface="browser",
         runtime_capabilities_overrides=None,
         cron_service=cron_service,
+        cron_pending_job_ids=cron_pending_job_ids,
     )
 
 
@@ -56,6 +58,7 @@ def _ch(
     port: int = _PORT,
     runtime_model_name: Any | None = None,
     cron_service: CronService | None = None,
+    cron_pending_job_ids: Any | None = None,
     **extra: Any,
 ) -> WebSocketChannel:
     cfg: dict[str, Any] = {
@@ -74,6 +77,7 @@ def _ch(
         workspace_path=workspace_path,
         runtime_model_name=runtime_model_name,
         cron_service=cron_service,
+        cron_pending_job_ids=cron_pending_job_ids,
     )
     return WebSocketChannel(cfg, bus, gateway=gateway)
 
@@ -177,11 +181,12 @@ async def test_session_automations_route_filters_by_webui_session(
 ) -> None:
     cron = CronService(tmp_path / "cron" / "jobs.json")
     hourly = CronSchedule(kind="every", every_ms=3_600_000)
+    pending_job_id = ""
     for name, message, to in (
         ("Morning check", "Check the project status", "abc"),
         ("Other session", "Do not show", "other"),
     ):
-        cron.add_job(
+        job = cron.add_job(
             name=name,
             schedule=hourly,
             message=message,
@@ -189,6 +194,8 @@ async def test_session_automations_route_filters_by_webui_session(
             origin_channel="websocket",
             origin_chat_id=to,
         )
+        if name == "Morning check":
+            pending_job_id = job.id
     cron.add_job(
         name="Legacy same target",
         schedule=hourly,
@@ -210,6 +217,7 @@ async def test_session_automations_route_filters_by_webui_session(
         bus,
         session_manager=_seed_session(tmp_path, key="websocket:abc"),
         cron_service=cron,
+        cron_pending_job_ids=lambda key: {pending_job_id} if key == "websocket:abc" else set(),
         port=29914,
     )
     server_task = asyncio.create_task(channel.start())
@@ -235,6 +243,8 @@ async def test_session_automations_route_filters_by_webui_session(
         assert job["schedule"]["kind"] == "every"
         assert job["schedule"]["every_ms"] == 3_600_000
         assert job["payload"]["message"] == "Check the project status"
+        assert job["state"]["pending"] is True
+        assert body["jobs"][1]["state"]["pending"] is False
     finally:
         await channel.stop()
         await server_task
diff --git a/tests/cli/test_commands.py b/tests/cli/test_commands.py
index abbd28427..c4372c44d 100644
--- a/tests/cli/test_commands.py
+++ b/tests/cli/test_commands.py
@@ -11,6 +11,7 @@ from typer.testing import CliRunner
 from nanobot.bus.events import InboundMessage, OutboundMessage
 from nanobot.cli.commands import app
 from nanobot.config.schema import Config
+from nanobot.cron.service import CronJobSkippedError
 from nanobot.cron.session_turns import CRON_DEFER_UNTIL_IDLE_META, CRON_TRIGGER_META
 from nanobot.cron.types import CronJob, CronPayload
 from nanobot.cron.webui_metadata import cron_proactive_delivery_metadata
@@ -1305,9 +1306,9 @@ def test_gateway_unbound_agent_cron_is_skipped(
         ),
     )
 
-    response = asyncio.run(cron.on_job(job))
+    with pytest.raises(CronJobSkippedError, match="unbound agent cron job"):
+        asyncio.run(cron.on_job(job))
 
-    assert response is None
     bus.publish_outbound.assert_not_awaited()
 
 
diff --git a/tests/cron/test_cron_service.py b/tests/cron/test_cron_service.py
index 7a0db0dd8..d81d4121b 100644
--- a/tests/cron/test_cron_service.py
+++ b/tests/cron/test_cron_service.py
@@ -4,7 +4,7 @@ import time
 
 import pytest
 
-from nanobot.cron.service import CronService
+from nanobot.cron.service import CronJobSkippedError, CronService
 from nanobot.cron.types import CronJob, CronPayload, CronSchedule
 
 
@@ -296,6 +296,30 @@ async def test_run_history_records_errors(tmp_path) -> None:
     assert loaded.state.run_history[0].error == "boom"
 
 
+@pytest.mark.asyncio
+async def test_run_history_records_skipped_jobs(tmp_path) -> None:
+    store_path = tmp_path / "cron" / "jobs.json"
+
+    async def skip(_):
+        raise CronJobSkippedError("missing session binding")
+
+    service = CronService(store_path, on_job=skip)
+    job = service.add_job(
+        name="skip",
+        schedule=CronSchedule(kind="every", every_ms=60_000),
+        message="hello",
+    )
+    await service.run_job(job.id)
+
+    loaded = service.get_job(job.id)
+    assert loaded is not None
+    assert loaded.state.last_status == "skipped"
+    assert loaded.state.last_error == "missing session binding"
+    assert len(loaded.state.run_history) == 1
+    assert loaded.state.run_history[0].status == "skipped"
+    assert loaded.state.run_history[0].error == "missing session binding"
+
+
 @pytest.mark.asyncio
 async def test_run_history_records_job_cancellation(tmp_path) -> None:
     store_path = tmp_path / "cron" / "jobs.json"
diff --git a/webui/src/App.tsx b/webui/src/App.tsx
index 9746e73f6..fa2976811 100644
--- a/webui/src/App.tsx
+++ b/webui/src/App.tsx
@@ -43,7 +43,7 @@ import type {
 } from "@/lib/types";
 import { Button } from "@/components/ui/button";
 import { Input } from "@/components/ui/input";
-import { fetchSessionAutomations, fetchSettings, fetchWorkspaces } from "@/lib/api";
+import { fetchSettings, fetchWorkspaces } from "@/lib/api";
 import {
   createRuntimeHost,
   getHostApi,
@@ -528,7 +528,15 @@ function Shell({
   const { t, i18n } = useTranslation();
   const { client, token } = useClient();
   const { theme, toggle } = useTheme();
-  const { sessions, loading, refresh, createChat, forkChat, deleteChat } = useSessions();
+  const {
+    sessions,
+    loading,
+    refresh,
+    createChat,
+    forkChat,
+    deleteChat,
+    getSessionAutomations,
+  } = useSessions();
   const { state: sidebarState, update: updateSidebarState } =
     useSidebarState(sessions, !loading);
   const initialRouteRef = useRef<ShellRoute | null>(null);
@@ -1306,12 +1314,12 @@ function Shell({
   const onRequestDelete = useCallback(async (key: string, label: string) => {
     let automations: SessionAutomationJob[] = [];
     try {
-      automations = (await fetchSessionAutomations(token, key)).jobs;
+      automations = await getSessionAutomations(key);
     } catch {
       // Delete remains protected by the backend block; prefetch only improves the first prompt.
     }
     setPendingDelete({ key, label, automations });
-  }, [token]);
+  }, [getSessionAutomations]);
 
   const headerTitle = activeSession
     ? sidebarState.title_overrides[activeSession.key] ||
diff --git a/webui/src/components/DeleteConfirm.tsx b/webui/src/components/DeleteConfirm.tsx
index 0f5e7f04c..fc73edd9c 100644
--- a/webui/src/components/DeleteConfirm.tsx
+++ b/webui/src/components/DeleteConfirm.tsx
@@ -51,9 +51,7 @@ export function DeleteConfirm({
           </AlertDialogTitle>
           <AlertDialogDescription className="mt-3 max-w-[17rem] text-center text-[14px] leading-6 text-muted-foreground">
             {hasAutomations
-              ? t("deleteConfirm.automationsDescription", {
-                  count: automations.length,
-                })
+              ? t("deleteConfirm.automationsDescription")
               : t("deleteConfirm.description")}
           </AlertDialogDescription>
           {hasAutomations ? (
@@ -94,9 +92,7 @@ export function DeleteConfirm({
             className="h-11 rounded-full bg-destructive px-5 text-[15px] font-semibold text-destructive-foreground shadow-[0_10px_25px_rgba(239,68,68,0.28)] hover:bg-destructive/90"
           >
             {hasAutomations
-              ? t("deleteConfirm.confirmWithAutomations", {
-                  count: automations.length,
-                })
+              ? t("deleteConfirm.confirmWithAutomations")
               : t("deleteConfirm.confirm")}
           </AlertDialogAction>
         </AlertDialogFooter>
diff --git a/webui/src/components/thread/SessionInfoPopover.tsx b/webui/src/components/thread/SessionInfoPopover.tsx
index 31df132bb..d69755dc2 100644
--- a/webui/src/components/thread/SessionInfoPopover.tsx
+++ b/webui/src/components/thread/SessionInfoPopover.tsx
@@ -176,6 +176,9 @@ function formatNextRun(job: SessionAutomationJob, t: TFunction, now: number) {
   if (!job.enabled) {
     return { label: t("thread.sessionInfo.next.disabled"), title: "" };
   }
+  if (job.state.pending) {
+    return { label: t("thread.sessionInfo.next.pending"), title: "" };
+  }
   const next = job.state.next_run_at_ms;
   if (!next) {
     return { label: t("thread.sessionInfo.next.none"), title: "" };
diff --git a/webui/src/hooks/useSessions.ts b/webui/src/hooks/useSessions.ts
index 43adaadd6..f1faea403 100644
--- a/webui/src/hooks/useSessions.ts
+++ b/webui/src/hooks/useSessions.ts
@@ -5,6 +5,7 @@ import i18n from "@/i18n";
 import {
   ApiError,
   deleteSession as apiDeleteSession,
+  fetchSessionAutomations,
   fetchWebuiThread,
   listSessions,
 } from "@/lib/api";
@@ -12,6 +13,7 @@ import { hasPendingAgentActivity } from "@/lib/activity-timeline";
 import { deriveTitle } from "@/lib/format";
 import type {
   ChatSummary,
+  SessionAutomationJob,
   SessionDeleteResult,
   UIMessage,
   WorkspaceScopePayload,
@@ -52,6 +54,7 @@ export function useSessions(): {
     key: string,
     options?: { deleteAutomations?: boolean },
   ) => Promise<SessionDeleteResult>;
+  getSessionAutomations: (key: string) => Promise<SessionAutomationJob[]>;
 } {
   const { client, token } = useClient();
   const [sessions, setSessions] = useState<ChatSummary[]>([]);
@@ -159,7 +162,21 @@ export function useSessions(): {
     [],
   );
 
-  return { sessions, loading, error, refresh, createChat, forkChat, deleteChat };
+  const getSessionAutomations = useCallback(async (key: string) => {
+    const result = await fetchSessionAutomations(tokenRef.current, key);
+    return result.jobs;
+  }, []);
+
+  return {
+    sessions,
+    loading,
+    error,
+    refresh,
+    createChat,
+    forkChat,
+    deleteChat,
+    getSessionAutomations,
+  };
 }
 
 /** Lazy-load a session's on-disk messages the first time the UI displays it. */
diff --git a/webui/src/i18n/locales/en/common.json b/webui/src/i18n/locales/en/common.json
index 3729d9e13..8020d3485 100644
--- a/webui/src/i18n/locales/en/common.json
+++ b/webui/src/i18n/locales/en/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "{{time}}",
+        "pending": "Runs shortly",
         "disabled": "Paused",
         "none": "No next run"
       }
diff --git a/webui/src/i18n/locales/es/common.json b/webui/src/i18n/locales/es/common.json
index 1cf97f7bd..46a6c3ab0 100644
--- a/webui/src/i18n/locales/es/common.json
+++ b/webui/src/i18n/locales/es/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "Siguiente {{time}}",
+        "pending": "Se ejecutará pronto",
         "disabled": "En pausa",
         "none": "Sin próxima ejecución"
       }
diff --git a/webui/src/i18n/locales/fr/common.json b/webui/src/i18n/locales/fr/common.json
index ed37dcb30..61182951c 100644
--- a/webui/src/i18n/locales/fr/common.json
+++ b/webui/src/i18n/locales/fr/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "Prochaine {{time}}",
+        "pending": "Exécution imminente",
         "disabled": "En pause",
         "none": "Aucune prochaine exécution"
       }
diff --git a/webui/src/i18n/locales/id/common.json b/webui/src/i18n/locales/id/common.json
index 2aae43477..12b8f1af3 100644
--- a/webui/src/i18n/locales/id/common.json
+++ b/webui/src/i18n/locales/id/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "Berikutnya {{time}}",
+        "pending": "Segera berjalan",
         "disabled": "Dijeda",
         "none": "Tidak ada jadwal berikutnya"
       }
diff --git a/webui/src/i18n/locales/ja/common.json b/webui/src/i18n/locales/ja/common.json
index 3100e98ba..1c2a19628 100644
--- a/webui/src/i18n/locales/ja/common.json
+++ b/webui/src/i18n/locales/ja/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "次回 {{time}}",
+        "pending": "まもなく実行",
         "disabled": "一時停止",
         "none": "次回実行なし"
       }
diff --git a/webui/src/i18n/locales/ko/common.json b/webui/src/i18n/locales/ko/common.json
index 952e48f68..e59c78cb8 100644
--- a/webui/src/i18n/locales/ko/common.json
+++ b/webui/src/i18n/locales/ko/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "다음 {{time}}",
+        "pending": "곧 실행됨",
         "disabled": "일시 중지됨",
         "none": "다음 실행 없음"
       }
diff --git a/webui/src/i18n/locales/vi/common.json b/webui/src/i18n/locales/vi/common.json
index 21faca3d7..22faba4e6 100644
--- a/webui/src/i18n/locales/vi/common.json
+++ b/webui/src/i18n/locales/vi/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "Tiếp theo {{time}}",
+        "pending": "Sắp chạy",
         "disabled": "Đã tạm dừng",
         "none": "Không có lần chạy tiếp theo"
       }
diff --git a/webui/src/i18n/locales/zh-CN/common.json b/webui/src/i18n/locales/zh-CN/common.json
index 29de0f71e..3ec1c3ac4 100644
--- a/webui/src/i18n/locales/zh-CN/common.json
+++ b/webui/src/i18n/locales/zh-CN/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "下次 {{time}}",
+        "pending": "即将执行",
         "disabled": "已暂停",
         "none": "没有下次运行"
       }
diff --git a/webui/src/i18n/locales/zh-TW/common.json b/webui/src/i18n/locales/zh-TW/common.json
index 9143f8047..70f2a6242 100644
--- a/webui/src/i18n/locales/zh-TW/common.json
+++ b/webui/src/i18n/locales/zh-TW/common.json
@@ -663,6 +663,7 @@
       },
       "next": {
         "label": "下次 {{time}}",
+        "pending": "即將執行",
         "disabled": "已暫停",
         "none": "沒有下次執行"
       }
diff --git a/webui/src/lib/types.ts b/webui/src/lib/types.ts
index df51f0887..aa7461f3e 100644
--- a/webui/src/lib/types.ts
+++ b/webui/src/lib/types.ts
@@ -113,6 +113,7 @@ export interface SessionAutomationJob {
   state: {
     next_run_at_ms?: number | null;
     last_status?: "ok" | "error" | "skipped" | string | null;
+    pending?: boolean;
   };
 }
 
diff --git a/webui/src/tests/app-layout.test.tsx b/webui/src/tests/app-layout.test.tsx
index 9e39688ba..d83d09965 100644
--- a/webui/src/tests/app-layout.test.tsx
+++ b/webui/src/tests/app-layout.test.tsx
@@ -1,12 +1,14 @@
 import { act, fireEvent, render, screen, waitFor, within } from "@testing-library/react";
 import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 
-import type { ChatSummary } from "@/lib/types";
+import i18n from "@/i18n";
+import type { ChatSummary, SessionAutomationJob } from "@/lib/types";
 
 const connectSpy = vi.fn();
 const refreshSpy = vi.fn();
 const createChatSpy = vi.fn().mockResolvedValue("chat-1");
 const deleteChatSpy = vi.fn();
+const getSessionAutomationsSpy = vi.fn<(key: string) => Promise<SessionAutomationJob[]>>();
 const toggleThemeSpy = vi.fn();
 const updateUrlSpy = vi.fn();
 const attachSpy = vi.fn();
@@ -146,6 +148,7 @@ vi.mock("@/hooks/useSessions", async (importOriginal) => {
         refresh: refreshSpy,
         createChat: createChatSpy,
         forkChat: async () => "fork-chat",
+        getSessionAutomations: getSessionAutomationsSpy,
         deleteChat: async (key: string, options?: { deleteAutomations?: boolean }) => {
           if (options === undefined) await deleteChatSpy(key);
           else await deleteChatSpy(key, options);
@@ -212,13 +215,15 @@ import { deriveWsUrl, fetchBootstrap } from "@/lib/bootstrap";
 import App from "@/App";
 
 describe("App layout", () => {
-  beforeEach(() => {
+  beforeEach(async () => {
+    await i18n.changeLanguage("en");
     mockSessions = [];
     connectSpy.mockClear();
     updateUrlSpy.mockClear();
     refreshSpy.mockReset();
     createChatSpy.mockClear();
     deleteChatSpy.mockReset();
+    getSessionAutomationsSpy.mockReset().mockResolvedValue([]);
     toggleThemeSpy.mockReset();
     attachSpy.mockReset();
     runStatusHandlers.clear();
@@ -435,7 +440,7 @@ describe("App layout", () => {
     expect(document.body.style.pointerEvents).not.toBe("none");
   }, 15_000);
 
-  it("shows bound automations in the first delete confirmation", async () => {
+  it("shows localized bound automations in the first delete confirmation", async () => {
     mockSessions = [
       {
         key: "websocket:chat-a",
@@ -454,44 +459,45 @@ describe("App layout", () => {
         preview: "Second chat",
       },
     ];
-    mockFetchRoutes({
-      "/api/sessions/websocket%3Achat-a/automations": {
-        jobs: [
-          {
-            id: "job-1",
-            name: "Daily repo check",
-            enabled: true,
-            schedule: { kind: "every", every_ms: 86_400_000 },
-            payload: { message: "Check the repo" },
-            state: { next_run_at_ms: Date.UTC(2026, 3, 17, 10, 0, 0) },
-          },
-        ],
+    getSessionAutomationsSpy.mockResolvedValue([
+      {
+        id: "job-1",
+        name: "Daily repo check",
+        enabled: true,
+        schedule: { kind: "every", every_ms: 86_400_000 },
+        payload: { message: "Check the repo" },
+        state: { next_run_at_ms: Date.UTC(2026, 3, 17, 10, 0, 0) },
       },
-    });
+    ]);
+    await i18n.changeLanguage("zh-CN");
 
     render(<App />);
 
     await waitFor(() => expect(connectSpy).toHaveBeenCalled());
-    const sidebar = screen.getByRole("navigation", { name: "Sidebar navigation" });
+    const sidebar = screen.getByRole("navigation", { name: "侧边栏导航" });
     await waitFor(() =>
       expect(
         within(sidebar).getByRole("button", { name: /^First chat$/ }),
       ).toBeInTheDocument(),
     );
 
-    fireEvent.pointerDown(screen.getByLabelText("Chat actions for First chat"), {
+    fireEvent.pointerDown(screen.getByLabelText(/First chat.*会话操作/), {
       button: 0,
     });
-    fireEvent.click(await screen.findByRole("menuitem", { name: "Delete" }));
+    fireEvent.click(await screen.findByRole("menuitem", { name: "删除" }));
 
     await waitFor(() =>
       expect(screen.getByText("Daily repo check")).toBeInTheDocument(),
     );
+    expect(getSessionAutomationsSpy).toHaveBeenCalledWith("websocket:chat-a");
     expect(
-      screen.getByText("This chat has scheduled automations. Deleting it will also delete them."),
+      screen.getByText("这个对话有关联的自动任务。删除对话也会删除这些自动任务。"),
     ).toBeInTheDocument();
+    expect(
+      screen.queryByText("This chat has scheduled automations. Deleting it will also delete them."),
+    ).not.toBeInTheDocument();
 
-    fireEvent.click(screen.getByRole("button", { name: "Delete chat and automations" }));
+    fireEvent.click(screen.getByRole("button", { name: "删除对话和自动任务" }));
 
     await waitFor(() =>
       expect(deleteChatSpy).toHaveBeenCalledWith("websocket:chat-a", {
diff --git a/webui/src/tests/session-info-popover.test.tsx b/webui/src/tests/session-info-popover.test.tsx
index 15da6986d..34fbc2e78 100644
--- a/webui/src/tests/session-info-popover.test.tsx
+++ b/webui/src/tests/session-info-popover.test.tsx
@@ -5,14 +5,17 @@ import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 import { SessionInfoPopover } from "@/components/thread/SessionInfoPopover";
 import { setAppLanguage } from "@/i18n";
 
-function automationJob(nextRunAt = Date.now() + 3_600_000) {
+function automationJob(
+  nextRunAt = Date.now() + 3_600_000,
+  state: Record<string, unknown> = {},
+) {
   return {
     id: "job-1",
     name: "Morning check",
     enabled: true,
     schedule: { kind: "every", every_ms: 3_600_000 },
     payload: { message: "Check the project status" },
-    state: { next_run_at_ms: nextRunAt },
+    state: { next_run_at_ms: nextRunAt, ...state },
   };
 }
 
@@ -27,7 +30,8 @@ function automationsResponse(jobs: unknown[]) {
 }
 
 describe("SessionInfoPopover", () => {
-  beforeEach(() => {
+  beforeEach(async () => {
+    await setAppLanguage("en");
     vi.stubGlobal(
       "fetch",
       vi.fn().mockResolvedValue(automationsResponse([automationJob()])),
@@ -86,6 +90,29 @@ describe("SessionInfoPopover", () => {
     expect(screen.queryByText("Automations")).not.toBeInTheDocument();
   });
 
+  it("shows a short pending label for deferred automations", async () => {
+    vi.stubGlobal(
+      "fetch",
+      vi.fn().mockResolvedValue(
+        automationsResponse([automationJob(Date.now() - 1000, { pending: true })]),
+      ),
+    );
+    const user = userEvent.setup();
+
+    render(
+      <SessionInfoPopover
+        sessionKey="websocket:chat-1"
+        token="tok"
+        title="Release work"
+      />,
+    );
+
+    await user.click(screen.getByRole("button", { name: "Session details" }));
+
+    expect(await screen.findByText("Runs shortly")).toBeInTheDocument();
+    expect(screen.queryByText(/ago/i)).not.toBeInTheDocument();
+  });
+
   it("refreshes while open so completed one-shot automations disappear", async () => {
     vi.stubGlobal(
       "fetch",