fix(cron): classify local script timeouts separately

cron/scheduler.py

@@ -58,6 +58,16 @@ def _summarize_cron_failure_for_delivery(job: dict, error: str | None) -> str:
     text = (error or "unknown error").strip()
     lower = text.lower()
 
+    # _run_job_script emits this exact envelope for local subprocess
+    # timeouts. Classify it before broad provider-keyword checks so a script
+    # path containing "429" or "rate-limit" cannot shadow the real cause.
+    if re.match(r"^script timed out after \d+(?:\.\d+)?s:", lower):
+        return (
+            f"⚠️ Cron '{job_name}' failed: local script timeout. "
+            "The pre-run script exceeded its execution limit. "
+            "Full details saved in cron output."
+        )
+
     # Provider/API failures are the common noisy path. Keep these short.
     if "429" in text or "rate limit" in lower or "usage limit" in lower:
         reason = "rate limit"

tests/cron/test_cron_script.py

@@ -195,6 +195,35 @@ def test_script_timeout(self, cron_env, monkeypatch):
         assert success is False
         assert "timed out" in output.lower()
 
+    def test_script_timeout_delivery_summary_stays_local(self, cron_env, monkeypatch):
+        import subprocess
+
+        from cron import scheduler as sched_mod
+        from cron.scheduler import (
+            _run_job_script,
+            _summarize_cron_failure_for_delivery,
+        )
+
+        script = cron_env / "scripts" / "429-rate-limit-report.py"
+        script.write_text("print('never runs')\n")
+
+        def raise_timeout(*args, **kwargs):
+            raise subprocess.TimeoutExpired(cmd=args[0], timeout=kwargs["timeout"])
+
+        monkeypatch.setattr(sched_mod.subprocess, "run", raise_timeout)
+        success, error = _run_job_script(str(script))
+
+        assert success is False
+        assert error.startswith("Script timed out after ")
+        summary = _summarize_cron_failure_for_delivery(
+            {"name": "nightly-report"}, error
+        )
+        assert "local script timeout" in summary
+        assert "provider timeout" not in summary
+        assert "provider rate limit" not in summary
+        assert "Fallback chain" not in summary
+        assert str(script) not in summary
+
     def test_script_json_output(self, cron_env):
         """Scripts can output structured JSON for the LLM to parse."""
         from cron.scheduler import _run_job_script

tests/cron/test_scheduler_failure_summary.py

@@ -0,0 +1,61 @@
+"""Regression tests for concise cron failure delivery summaries."""
+
+from cron.scheduler import _summarize_cron_failure_for_delivery
+
+
+JOB = {"id": "job-1", "name": "nightly-report"}
+
+
+def summarize(error: str) -> str:
+    return _summarize_cron_failure_for_delivery(JOB, error)
+
+
+def test_local_script_timeout_is_not_labelled_as_provider_failure():
+    result = summarize("Script timed out after 120s: /tmp/foo.py")
+
+    assert "local script timeout" in result
+    assert "provider timeout" not in result
+    assert "Fallback chain" not in result
+    assert "/tmp/foo.py" not in result
+
+
+def test_decimal_local_script_timeout_is_classified_locally():
+    result = summarize("Script timed out after 1.5s: /tmp/foo.py")
+
+    assert "local script timeout" in result
+    assert "provider timeout" not in result
+
+
+def test_local_timeout_path_containing_429_does_not_become_rate_limit():
+    result = summarize("Script timed out after 30s: /tmp/429-report.py")
+
+    assert "local script timeout" in result
+    assert "provider rate limit" not in result
+
+
+def test_local_timeout_path_containing_rate_limit_stays_local():
+    result = summarize("Script timed out after 30s: /tmp/rate-limit-report.py")
+
+    assert "local script timeout" in result
+    assert "provider rate limit" not in result
+
+
+def test_readtimeout_remains_a_provider_timeout():
+    result = summarize("ReadTimeout: request timed out")
+
+    assert "provider timeout" in result
+    assert "Fallback chain" in result
+
+
+def test_normal_script_failure_remains_generic_and_sanitized():
+    result = summarize("Script execution failed: permission denied")
+
+    assert result == "⚠️ Cron 'nightly-report' failed: Script execution failed: permission denied"
+    assert "provider timeout" not in result
+
+
+def test_incidental_timeout_wording_does_not_match_local_script_envelope():
+    result = summarize("Script reported timeout statistics")
+
+    assert "local script timeout" not in result
+    assert "provider timeout" in result