diff --git a/routes/calendar_routes.py b/routes/calendar_routes.py
index 7aa812c25..0a30d9205 100644
--- a/routes/calendar_routes.py
+++ b/routes/calendar_routes.py
@@ -258,6 +258,17 @@ def parse_due_for_user(s: str) -> str:
         if t is not None:
             return base.replace(hour=t[0], minute=t[1]).isoformat()
 
+    # Time-first: "3pm today", "11pm today", "9am tomorrow"
+    m = _re.match(r'^(.+?)\s+(today|tonight|tomorrow|tmrw|yesterday)$', lower)
+    if m:
+        time_part, word = m.group(1).strip(), m.group(2)
+        base = today
+        if word in ("tomorrow", "tmrw"): base = today + _td(days=1)
+        elif word == "yesterday":        base = today - _td(days=1)
+        t = _parse_time(time_part)
+        if t is not None:
+            return base.replace(hour=t[0], minute=t[1]).isoformat()
+
     m = _re.match(r'^in\s+(\d+)\s*(hour|hr|minute|min|day)s?\s*$', lower)
     if m:
         n = int(m.group(1)); unit = m.group(2)
diff --git a/tests/test_parse_due_time_first.py b/tests/test_parse_due_time_first.py
new file mode 100644
index 000000000..3bb63fd42
--- /dev/null
+++ b/tests/test_parse_due_time_first.py
@@ -0,0 +1,63 @@
+"""Regression: parse_due_for_user must handle time-first phrasings.
+
+The tool schema and tool_index both advertise '11pm today' as a valid
+due_date example. The parser's natural-language branch only matched
+day-first format ('today at 11pm'), so time-first strings like '3pm today'
+raised ValueError, fell back to the raw string, and the ISO-only reminder
+scanner never fired the note. Fixes #3302.
+"""
+from datetime import datetime, timezone
+
+import routes.calendar_routes as calendar_routes
+from src.user_time import clear_user_time_context, set_user_tz_name, set_user_tz_offset
+
+
+class _FixedNow(datetime):
+    """Freeze server clock at 2026-06-07T10:00:00 UTC for deterministic tests."""
+    @classmethod
+    def now(cls, tz=None):
+        value = datetime(2026, 6, 7, 10, 0, 0, tzinfo=timezone.utc)
+        if tz is not None:
+            return value.astimezone(tz)
+        return value.replace(tzinfo=None)
+
+
+def setup_function():
+    clear_user_time_context()
+    set_user_tz_offset(0)
+    set_user_tz_name("UTC")
+
+
+def teardown_function():
+    clear_user_time_context()
+
+
+def test_time_first_today(monkeypatch):
+    monkeypatch.setattr(calendar_routes, "datetime", _FixedNow)
+    result = calendar_routes.parse_due_for_user("3pm today")
+    assert result.startswith("2026-06-07T15:00:00")
+
+
+def test_time_first_today_11pm(monkeypatch):
+    monkeypatch.setattr(calendar_routes, "datetime", _FixedNow)
+    result = calendar_routes.parse_due_for_user("11pm today")
+    assert result.startswith("2026-06-07T23:00:00")
+
+
+def test_time_first_tomorrow(monkeypatch):
+    monkeypatch.setattr(calendar_routes, "datetime", _FixedNow)
+    result = calendar_routes.parse_due_for_user("9am tomorrow")
+    assert result.startswith("2026-06-08T09:00:00")
+
+
+def test_time_first_with_minutes(monkeypatch):
+    monkeypatch.setattr(calendar_routes, "datetime", _FixedNow)
+    result = calendar_routes.parse_due_for_user("2:30pm tomorrow")
+    assert result.startswith("2026-06-08T14:30:00")
+
+
+def test_day_first_still_works(monkeypatch):
+    """Existing day-first format must not regress."""
+    monkeypatch.setattr(calendar_routes, "datetime", _FixedNow)
+    result = calendar_routes.parse_due_for_user("today at 3pm")
+    assert result.startswith("2026-06-07T15:00:00")