diff --git a/routes/calendar_routes.py b/routes/calendar_routes.py
index 137fde9..1352e40 100644
--- a/routes/calendar_routes.py
+++ b/routes/calendar_routes.py
@@ -470,8 +470,21 @@ def _expand_rrule(
         return [d]
 
     # Parse the rrule, applying it to the base dtstart.
+    rrule_str = ev.rrule
+    if ev.dtstart is not None and getattr(ev.dtstart, "tzinfo", None) is None:
+        # Events are stored with a naive (UTC) dtstart, but standard .ics
+        # exporters (Google/Apple/Outlook/Fastmail) write the bound as an
+        # absolute UTC value, e.g. UNTIL=20240105T090000Z. dateutil refuses to
+        # mix a tz-aware UNTIL with a naive DTSTART ("RRULE UNTIL values must be
+        # specified in UTC when DTSTART is timezone-aware"), so the except branch
+        # below would silently collapse the whole series to a single event.
+        # Drop the trailing Z so UNTIL matches the naive DTSTART.
+        import re as _re
+        rrule_str = _re.sub(
+            r"(UNTIL=\d{8}(?:T\d{6})?)Z", r"\1", rrule_str, flags=_re.IGNORECASE
+        )
     try:
-        rule = rrulestr(ev.rrule, dtstart=ev.dtstart)
+        rule = rrulestr(rrule_str, dtstart=ev.dtstart)
     except Exception as ex:
         logger.warning(
             "Failed to parse rrule=%r for event %s: %s", ev.rrule, ev.uid, ex
diff --git a/tests/test_calendar_rrule_until_utc.py b/tests/test_calendar_rrule_until_utc.py
new file mode 100644
index 0000000..9aade26
--- /dev/null
+++ b/tests/test_calendar_rrule_until_utc.py
@@ -0,0 +1,73 @@
+"""Regression test for RRULE expansion with a UTC UNTIL value.
+
+Standard ICS exporters (Google Calendar, Apple Calendar, Outlook,
+Fastmail) emit recurrence rules of the form
+
+    RRULE:FREQ=DAILY;UNTIL=20240105T090000Z
+
+When such an event is imported, the calendar route stores the event's
+``dtstart`` as a *naive* datetime (the DB column is naive; timed events
+are converted to naive-UTC on import). dateutil >= 2.7 raises
+
+    ValueError: RRULE UNTIL values must be specified in UTC
+                when DTSTART is timezone-aware
+
+whenever the UNTIL is tz-aware (carries a trailing ``Z``) but the
+``dtstart`` is naive. ``_expand_rrule`` catches that ValueError and
+*silently downgrades the event to non-recurring*, so every occurrence
+after the first vanishes from the calendar.
+
+This test pins the correct behaviour: a daily series bounded by a UTC
+UNTIL must expand to all of its occurrences.
+"""
+
+from datetime import datetime
+from types import SimpleNamespace
+
+from tests.test_null_owner_gates import _import_calendar_helpers
+
+
+_MOCK_CAL = SimpleNamespace(name="Personal", color="#5b8abf")
+
+
+def _make_event(**overrides):
+    defaults = {
+        "uid": "evt-until-utc",
+        "summary": "Standup",
+        "dtstart": datetime(2024, 1, 1, 9, 0),
+        "dtend": datetime(2024, 1, 1, 9, 30),
+        "all_day": False,
+        "is_utc": True,
+        "rrule": "",
+        "calendar_id": "cal-001",
+        "color": None,
+        "description": "",
+        "location": "",
+        "event_type": None,
+        "importance": "normal",
+    }
+    defaults.update(overrides)
+    ev = SimpleNamespace(**defaults)
+    ev.calendar = _MOCK_CAL
+    return ev
+
+
+def test_expand_rrule_with_utc_until_keeps_all_occurrences():
+    """FREQ=DAILY;UNTIL=...Z must expand to every occurrence, not collapse
+    to a single non-recurring event."""
+    cal = _import_calendar_helpers()
+    ev = _make_event(rrule="FREQ=DAILY;UNTIL=20240105T090000Z")
+
+    results = cal._expand_rrule(ev, datetime(2024, 1, 1), datetime(2024, 1, 10))
+
+    # Jan 1, 2, 3, 4, 5 — five daily occurrences up to and including UNTIL.
+    assert len(results) == 5, (
+        f"Expected 5 daily occurrences bounded by UTC UNTIL, got "
+        f"{len(results)}: {[r['uid'] for r in results]}"
+    )
+    assert all(r["is_recurrence"] is True for r in results), (
+        "Occurrences must be flagged as recurrences, not silently downgraded "
+        f"to non-recurring: {[(r['uid'], r['is_recurrence']) for r in results]}"
+    )
+    assert results[0]["uid"] == "evt-until-utc::2024-01-01T09:00"
+    assert results[-1]["uid"] == "evt-until-utc::2024-01-05T09:00"