diff --git a/backend/open_webui/routers/calendar.py b/backend/open_webui/routers/calendar.py
index 86d9824803..acd434451d 100644
--- a/backend/open_webui/routers/calendar.py
+++ b/backend/open_webui/routers/calendar.py
@@ -26,6 +26,7 @@ from open_webui.models.users import UserModel
 from open_webui.utils.access_control import filter_allowed_access_grants, has_permission
 from open_webui.utils.auth import get_verified_user
 from open_webui.utils.calendar import expand_recurring_event
+from open_webui.utils.recurrence import schedule_start_ns
 
 log = logging.getLogger(__name__)
 
@@ -206,13 +207,22 @@ async def get_events(
                 if not rrule_str:
                     continue
 
+                start_at = auto.next_run_at or 0
+                upper_rrule = rrule_str.upper()
+                if 'COUNT=' in upper_rrule and 'DTSTART' in upper_rrule:
+                    # COUNT runs from DTSTART, anchoring on the next run would restart it
+                    try:
+                        start_at = schedule_start_ns(rrule_str, user.timezone)
+                    except ValueError:
+                        pass
+
                 virtual = {
                     'id': f'auto_{auto.id}',
                     'calendar_id': SCHEDULED_TASKS_CALENDAR_ID,
                     'user_id': user.id,
                     'title': auto.name,
                     'description': auto.data.get('prompt', '') if auto.data else '',
-                    'start_at': auto.next_run_at or 0,
+                    'start_at': start_at,
                     'end_at': None,
                     'all_day': False,
                     'rrule': rrule_str,
diff --git a/backend/open_webui/utils/calendar.py b/backend/open_webui/utils/calendar.py
index 063cbc8e3c..b7815da628 100644
--- a/backend/open_webui/utils/calendar.py
+++ b/backend/open_webui/utils/calendar.py
@@ -60,7 +60,7 @@ def expand_recurring_event(
 
     instances = []
     previous_start = None
-    for occurrence_start in rule.xafter(scan_start, count=max_instances, inc=True):
+    for occurrence_start in rule.xafter(scan_start, inc=True):
         if occurrence_start >= range_end or occurrence_start == previous_start:
             break
         previous_start = occurrence_start
@@ -76,6 +76,8 @@ def expand_recurring_event(
                 'instance_id': f'{event_dict["id"]}_{instance_start_ns}',
             }
             instances.append(instance)
+            if len(instances) >= max_instances:
+                break
 
     return instances
 
diff --git a/backend/open_webui/utils/recurrence.py b/backend/open_webui/utils/recurrence.py
index c4817eca07..717953cc6b 100644
--- a/backend/open_webui/utils/recurrence.py
+++ b/backend/open_webui/utils/recurrence.py
@@ -148,6 +148,18 @@ async def next_run_ns(s: str, tz: str = None) -> Optional[int]:
     return int(dt.timestamp() * 1_000_000_000)
 
 
+def schedule_start_ns(s: str, tz: str = None) -> int:
+    """DTSTART the scheduler anchors the rule to, as epoch nanoseconds."""
+    zi = _resolve_tz(tz)
+    now = datetime.now(zi).replace(tzinfo=None) if zi else datetime.now()
+    parsed = _parse_rule(s, now)
+    rule = parsed._rrule[0] if isinstance(parsed, rruleset) else parsed
+    dt = rule._dtstart
+    if zi:
+        dt = dt.replace(tzinfo=zi)
+    return int(dt.timestamp() * 1_000_000_000)
+
+
 async def next_n_runs_ns(s: str, n: int = 5, tz: str = None) -> list[int]:
     """Compute next N occurrences for UI preview.