diff --git a/tests/test_timezone.py b/tests/test_timezone.py
index 9902817d8..728d47dd9 100644
--- a/tests/test_timezone.py
+++ b/tests/test_timezone.py
@@ -328,6 +328,34 @@ def test_ensure_aware_due_job_not_skipped_when_system_ahead(self, tmp_path, monk
             "Overdue job was skipped — _ensure_aware likely shifted absolute time"
         )
 
+    def test_get_due_jobs_naive_cross_timezone(self, tmp_path, monkeypatch):
+        """Naive past timestamps must be detected as due even when Hermes tz
+        is behind system local tz — the scenario that triggered #806."""
+        import cron.jobs as jobs_module
+        monkeypatch.setattr(jobs_module, "CRON_DIR", tmp_path / "cron")
+        monkeypatch.setattr(jobs_module, "JOBS_FILE", tmp_path / "cron" / "jobs.json")
+        monkeypatch.setattr(jobs_module, "OUTPUT_DIR", tmp_path / "cron" / "output")
+
+        # Use a Hermes timezone far behind UTC so that the numeric wall time
+        # of the naive timestamp exceeds _hermes_now's wall time — this would
+        # have caused a false "not due" with the old replace(tzinfo=...) approach.
+        os.environ["HERMES_TIMEZONE"] = "Pacific/Midway"  # UTC-11
+        hermes_time.reset_cache()
+
+        from cron.jobs import create_job, load_jobs, save_jobs, get_due_jobs
+        create_job(prompt="Cross-tz job", schedule="every 1h")
+        jobs = load_jobs()
+
+        # Force a naive past timestamp (system-local wall time, 10 min ago)
+        naive_past = (datetime.now() - timedelta(minutes=10)).isoformat()
+        jobs[0]["next_run_at"] = naive_past
+        save_jobs(jobs)
+
+        due = get_due_jobs()
+        assert len(due) == 1, (
+            "Naive past timestamp should be due regardless of Hermes timezone"
+        )
+
     def test_create_job_stores_tz_aware_timestamps(self, tmp_path, monkeypatch):
         """New jobs store timezone-aware created_at and next_run_at."""
         import cron.jobs as jobs_module