diff --git a/cron/jobs.py b/cron/jobs.py
index 0c062cfea3..6cbb168f0c 100644
--- a/cron/jobs.py
+++ b/cron/jobs.py
@@ -168,16 +168,22 @@ def parse_schedule(schedule: str) -> Dict[str, Any]:
 
 
 def _ensure_aware(dt: datetime) -> datetime:
-    """Make a naive datetime tz-aware using the configured timezone.
+    """Return a timezone-aware datetime in Hermes configured timezone.
 
-    Handles backward compatibility: timestamps stored before timezone support
-    are naive (server-local).  We assume they were in the same timezone as
-    the current configuration so comparisons work without crashing.
+    Backward compatibility:
+    - Older stored timestamps may be naive.
+    - Naive values are interpreted as *system-local wall time* (the timezone
+      `datetime.now()` used when they were created), then converted to the
+      configured Hermes timezone.
+
+    This preserves relative ordering for legacy naive timestamps across
+    timezone changes and avoids false not-due results.
     """
+    target_tz = _hermes_now().tzinfo
     if dt.tzinfo is None:
-        tz = _hermes_now().tzinfo
-        return dt.replace(tzinfo=tz)
-    return dt
+        local_tz = datetime.now().astimezone().tzinfo
+        return dt.replace(tzinfo=local_tz).astimezone(target_tz)
+    return dt.astimezone(target_tz)
 
 
 def compute_next_run(schedule: Dict[str, Any], last_run_at: Optional[str] = None) -> Optional[str]:
diff --git a/tests/test_timezone.py b/tests/test_timezone.py
index 3d657989e0..a0949fe0da 100644
--- a/tests/test_timezone.py
+++ b/tests/test_timezone.py
@@ -249,6 +249,76 @@ class TestCronTimezone:
         due = get_due_jobs()
         assert len(due) == 1
 
+    def test_ensure_aware_naive_preserves_absolute_time(self, monkeypatch):
+        """_ensure_aware should interpret naive datetimes as system-local time,
+        not blindly stamp them with the Hermes timezone."""
+        import cron.jobs as jobs_module
+
+        hermes_tz = ZoneInfo("America/New_York")
+
+        # Mock _hermes_now so its .tzinfo returns the Hermes timezone
+        mock_now = datetime(2026, 3, 11, 12, 0, 0, tzinfo=hermes_tz)
+        monkeypatch.setattr(jobs_module, "_hermes_now", lambda: mock_now)
+
+        # A naive datetime — represents system-local wall time
+        naive_dt = datetime(2026, 3, 11, 17, 25, 0)
+
+        result = jobs_module._ensure_aware(naive_dt)
+
+        # Result must be in Hermes timezone
+        assert result.tzinfo is not None
+
+        # The absolute time should match interpreting naive_dt as system-local
+        system_local_tz = datetime.now().astimezone().tzinfo
+        expected = naive_dt.replace(tzinfo=system_local_tz).astimezone(hermes_tz)
+        assert result == expected
+
+    def test_ensure_aware_normalizes_aware_to_hermes_tz(self, monkeypatch):
+        """Already-aware datetimes should be normalized to Hermes timezone."""
+        import cron.jobs as jobs_module
+
+        hermes_tz = ZoneInfo("America/New_York")
+        mock_now = datetime(2026, 3, 11, 12, 0, 0, tzinfo=hermes_tz)
+        monkeypatch.setattr(jobs_module, "_hermes_now", lambda: mock_now)
+
+        # An aware datetime in a different timezone
+        utc_dt = datetime(2026, 3, 11, 17, 0, 0, tzinfo=ZoneInfo("UTC"))
+        result = jobs_module._ensure_aware(utc_dt)
+
+        # Should be the same absolute time, but in Hermes tz
+        assert result.tzinfo is not None
+        assert result == utc_dt.astimezone(hermes_tz)
+        # Verify the wall-clock time shifted (UTC-4 during DST)
+        assert result.hour == 13  # 17:00 UTC = 13:00 EDT
+
+    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