feat(cron): track delivery failures in job status (#6042)

_deliver_result() now returns Optional[str] — None on success, error
message on failure. All failure paths (unknown platform, platform
disabled, config load error, send failure, unresolvable target)
return descriptive error strings.

mark_job_run() gains delivery_error param, tracked as
last_delivery_error on the job — separate from agent execution errors.
A job where the agent succeeded but delivery failed shows
last_status='ok' + last_delivery_error='...'.

The cronjob list tool now surfaces last_delivery_error so agents and
users can see when cron outputs aren't arriving.

Inspired by PR #5863 (oxngon) — reimplemented with proper wiring.

Tests: 3 new mark_job_run tests + 6 new _deliver_result return tests.

cron/jobs.py

@@ -574,12 +574,16 @@ def remove_job(job_id: str) -> bool:
     return False
 
 
-def mark_job_run(job_id: str, success: bool, error: Optional[str] = None):
+def mark_job_run(job_id: str, success: bool, error: Optional[str] = None,
+                 delivery_error: Optional[str] = None):
     """
     Mark a job as having been run.
     
     Updates last_run_at, last_status, increments completed count,
     computes next_run_at, and auto-deletes if repeat limit reached.
+
+    ``delivery_error`` is tracked separately from the agent error — a job
+    can succeed (agent produced output) but fail delivery (platform down).
     """
     jobs = load_jobs()
     for i, job in enumerate(jobs):
@@ -588,6 +592,8 @@ def mark_job_run(job_id: str, success: bool, error: Optional[str] = None):
             job["last_run_at"] = now
             job["last_status"] = "ok" if success else "error"
             job["last_error"] = error if not success else None
+            # Track delivery failures separately — cleared on successful delivery
+            job["last_delivery_error"] = delivery_error
             
             # Increment completed count
             if job.get("repeat"):

cron/scheduler.py

@@ -196,7 +196,7 @@ def _send_media_via_adapter(adapter, chat_id: str, media_files: list, metadata:
             logger.warning("Job '%s': failed to send media %s: %s", job.get("id", "?"), media_path, e)
 
 
-def _deliver_result(job: dict, content: str, adapters=None, loop=None) -> None:
+def _deliver_result(job: dict, content: str, adapters=None, loop=None) -> Optional[str]:
     """
     Deliver job output to the configured target (origin chat, specific platform, etc.).
 
@@ -204,16 +204,16 @@ def _deliver_result(job: dict, content: str, adapters=None, loop=None) -> None:
     use the live adapter first — this supports E2EE rooms (e.g. Matrix) where
     the standalone HTTP path cannot encrypt.  Falls back to standalone send if
     the adapter path fails or is unavailable.
+
+    Returns None on success, or an error string on failure.
     """
     target = _resolve_delivery_target(job)
     if not target:
         if job.get("deliver", "local") != "local":
-            logger.warning(
+            msg = f"no delivery target resolved for deliver={job.get('deliver', 'local')}"
-                "Job '%s' deliver=%s but no concrete delivery target could be resolved",
+            logger.warning("Job '%s': %s", job["id"], msg)
-                job["id"],
+            return msg
-                job.get("deliver", "local"),
+        return None  # local-only jobs don't deliver — not a failure
-            )
-        return
 
     platform_name = target["platform"]
     chat_id = target["chat_id"]
@@ -239,19 +239,22 @@ def _deliver_result(job: dict, content: str, adapters=None, loop=None) -> None:
     }
     platform = platform_map.get(platform_name.lower())
     if not platform:
-        logger.warning("Job '%s': unknown platform '%s' for delivery", job["id"], platform_name)
+        msg = f"unknown platform '{platform_name}'"
-        return
+        logger.warning("Job '%s': %s", job["id"], msg)
+        return msg
 
     try:
         config = load_gateway_config()
     except Exception as e:
-        logger.error("Job '%s': failed to load gateway config for delivery: %s", job["id"], e)
+        msg = f"failed to load gateway config: {e}"
-        return
+        logger.error("Job '%s': %s", job["id"], msg)
+        return msg
 
     pconfig = config.platforms.get(platform)
     if not pconfig or not pconfig.enabled:
-        logger.warning("Job '%s': platform '%s' not configured/enabled", job["id"], platform_name)
+        msg = f"platform '{platform_name}' not configured/enabled"
-        return
+        logger.warning("Job '%s': %s", job["id"], msg)
+        return msg
 
     # Optionally wrap the content with a header/footer so the user knows this
     # is a cron delivery.  Wrapping is on by default; set cron.wrap_response: false
@@ -307,7 +310,7 @@ def _deliver_result(job: dict, content: str, adapters=None, loop=None) -> None:
 
             if adapter_ok:
                 logger.info("Job '%s': delivered to %s:%s via live adapter", job["id"], platform_name, chat_id)
-                return
+                return None
         except Exception as e:
             logger.warning(
                 "Job '%s': live adapter delivery to %s:%s failed (%s), falling back to standalone",
@@ -329,13 +332,17 @@ def _deliver_result(job: dict, content: str, adapters=None, loop=None) -> None:
             future = pool.submit(asyncio.run, _send_to_platform(platform, pconfig, chat_id, cleaned_delivery_content, thread_id=thread_id, media_files=media_files))
             result = future.result(timeout=30)
     except Exception as e:
-        logger.error("Job '%s': delivery to %s:%s failed: %s", job["id"], platform_name, chat_id, e)
+        msg = f"delivery to {platform_name}:{chat_id} failed: {e}"
-        return
+        logger.error("Job '%s': %s", job["id"], msg)
+        return msg
 
     if result and result.get("error"):
-        logger.error("Job '%s': delivery error: %s", job["id"], result["error"])
+        msg = f"delivery error: {result['error']}"
-    else:
+        logger.error("Job '%s': %s", job["id"], msg)
+        return msg
+
     logger.info("Job '%s': delivered to %s:%s", job["id"], platform_name, chat_id)
+    return None
 
 
 _SCRIPT_TIMEOUT = 120  # seconds
@@ -868,13 +875,15 @@ def tick(verbose: bool = True, adapters=None, loop=None) -> int:
                     logger.info("Job '%s': agent returned %s — skipping delivery", job["id"], SILENT_MARKER)
                     should_deliver = False
 
+                delivery_error = None
                 if should_deliver:
                     try:
-                        _deliver_result(job, deliver_content, adapters=adapters, loop=loop)
+                        delivery_error = _deliver_result(job, deliver_content, adapters=adapters, loop=loop)
                     except Exception as de:
+                        delivery_error = str(de)
                         logger.error("Delivery failed for job %s: %s", job["id"], de)
 
-                mark_job_run(job["id"], success, error)
+                mark_job_run(job["id"], success, error, delivery_error=delivery_error)
                 executed += 1
 
             except Exception as e:

hermes_cli/cron.py

@@ -93,6 +93,21 @@ def cron_list(show_all: bool = False):
         script = job.get("script")
         if script:
             print(f"    Script:    {script}")
+
+        # Execution history
+        last_status = job.get("last_status")
+        if last_status:
+            last_run = job.get("last_run_at", "?")
+            if last_status == "ok":
+                status_display = color("ok", Colors.GREEN)
+            else:
+                status_display = color(f"{last_status}: {job.get('last_error', '?')}", Colors.RED)
+            print(f"    Last run:  {last_run}  {status_display}")
+
+        delivery_err = job.get("last_delivery_error")
+        if delivery_err:
+            print(f"    {color('⚠ Delivery failed:', Colors.YELLOW)} {delivery_err}")
+
         print()
 
     from hermes_cli.gateway import find_gateway_pids

tests/cron/test_jobs.py

@@ -339,6 +339,36 @@ class TestMarkJobRun:
         assert updated["last_status"] == "error"
         assert updated["last_error"] == "timeout"
 
+    def test_delivery_error_tracked_separately(self, tmp_cron_dir):
+        """Agent succeeds but delivery fails — both tracked independently."""
+        job = create_job(prompt="Report", schedule="every 1h")
+        mark_job_run(job["id"], success=True, delivery_error="platform 'telegram' not configured")
+        updated = get_job(job["id"])
+        assert updated["last_status"] == "ok"
+        assert updated["last_error"] is None
+        assert updated["last_delivery_error"] == "platform 'telegram' not configured"
+
+    def test_delivery_error_cleared_on_success(self, tmp_cron_dir):
+        """Successful delivery clears the previous delivery error."""
+        job = create_job(prompt="Report", schedule="every 1h")
+        mark_job_run(job["id"], success=True, delivery_error="network timeout")
+        updated = get_job(job["id"])
+        assert updated["last_delivery_error"] == "network timeout"
+        # Next run delivers successfully
+        mark_job_run(job["id"], success=True, delivery_error=None)
+        updated = get_job(job["id"])
+        assert updated["last_delivery_error"] is None
+
+    def test_both_agent_and_delivery_error(self, tmp_cron_dir):
+        """Agent fails AND delivery fails — both errors recorded."""
+        job = create_job(prompt="Report", schedule="every 1h")
+        mark_job_run(job["id"], success=False, error="model timeout",
+                     delivery_error="platform 'discord' not enabled")
+        updated = get_job(job["id"])
+        assert updated["last_status"] == "error"
+        assert updated["last_error"] == "model timeout"
+        assert updated["last_delivery_error"] == "platform 'discord' not enabled"
+
 
 class TestAdvanceNextRun:
     """Tests for advance_next_run() — crash-safety for recurring jobs."""

tests/cron/test_scheduler.py

@@ -508,6 +508,90 @@ class TestDeliverResultWrapping:
         assert send_mock.call_args.kwargs["thread_id"] == "17585"
 
 
+class TestDeliverResultErrorReturns:
+    """Verify _deliver_result returns error strings on failure, None on success."""
+
+    def test_returns_none_on_successful_delivery(self):
+        from gateway.config import Platform
+
+        pconfig = MagicMock()
+        pconfig.enabled = True
+        mock_cfg = MagicMock()
+        mock_cfg.platforms = {Platform.TELEGRAM: pconfig}
+
+        with patch("gateway.config.load_gateway_config", return_value=mock_cfg), \
+             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})):
+            job = {
+                "id": "ok-job",
+                "deliver": "origin",
+                "origin": {"platform": "telegram", "chat_id": "123"},
+            }
+            result = _deliver_result(job, "Output.")
+        assert result is None
+
+    def test_returns_none_for_local_delivery(self):
+        """local-only jobs don't deliver — not a failure."""
+        job = {"id": "local-job", "deliver": "local"}
+        result = _deliver_result(job, "Output.")
+        assert result is None
+
+    def test_returns_error_for_unknown_platform(self):
+        job = {
+            "id": "bad-platform",
+            "deliver": "origin",
+            "origin": {"platform": "fax", "chat_id": "123"},
+        }
+        with patch("gateway.config.load_gateway_config"):
+            result = _deliver_result(job, "Output.")
+        assert result is not None
+        assert "unknown platform" in result
+
+    def test_returns_error_when_platform_disabled(self):
+        from gateway.config import Platform
+
+        pconfig = MagicMock()
+        pconfig.enabled = False
+        mock_cfg = MagicMock()
+        mock_cfg.platforms = {Platform.TELEGRAM: pconfig}
+
+        with patch("gateway.config.load_gateway_config", return_value=mock_cfg):
+            job = {
+                "id": "disabled",
+                "deliver": "origin",
+                "origin": {"platform": "telegram", "chat_id": "123"},
+            }
+            result = _deliver_result(job, "Output.")
+        assert result is not None
+        assert "not configured" in result
+
+    def test_returns_error_on_send_failure(self):
+        from gateway.config import Platform
+
+        pconfig = MagicMock()
+        pconfig.enabled = True
+        mock_cfg = MagicMock()
+        mock_cfg.platforms = {Platform.TELEGRAM: pconfig}
+
+        with patch("gateway.config.load_gateway_config", return_value=mock_cfg), \
+             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"error": "rate limited"})):
+            job = {
+                "id": "rate-limited",
+                "deliver": "origin",
+                "origin": {"platform": "telegram", "chat_id": "123"},
+            }
+            result = _deliver_result(job, "Output.")
+        assert result is not None
+        assert "rate limited" in result
+
+    def test_returns_error_for_unresolved_target(self, monkeypatch):
+        """Non-local delivery with no resolvable target should return an error."""
+        monkeypatch.delenv("TELEGRAM_HOME_CHANNEL", raising=False)
+        job = {"id": "no-target", "deliver": "telegram"}
+        result = _deliver_result(job, "Output.")
+        assert result is not None
+        assert "no delivery target" in result
+
+
 class TestRunJobSessionPersistence:
     def test_run_job_passes_session_db_and_cron_platform(self, tmp_path):
         job = {

tools/cronjob_tools.py

@@ -195,6 +195,7 @@ def _format_job(job: Dict[str, Any]) -> Dict[str, Any]:
         "next_run_at": job.get("next_run_at"),
         "last_run_at": job.get("last_run_at"),
         "last_status": job.get("last_status"),
+        "last_delivery_error": job.get("last_delivery_error"),
         "enabled": job.get("enabled", True),
         "state": job.get("state", "scheduled" if job.get("enabled", True) else "paused"),
         "paused_at": job.get("paused_at"),