Fix naive/aware datetime comparison for user expiration.

Co-authored-by: Cursor <cursoragent@cursor.com>

app.py

@@ -1855,16 +1855,18 @@ async def periodic_background_tasks():
                                     if uid not in to_disable_uids:
                                         to_disable_uids.append(uid)
                                 
-                                # Check expiration date
+                                # Check expiration date (naive/aware-safe)
-                                exp_str = u.get('expiration_date')
+                                if u.get('enabled', True):
-                                if exp_str and u.get('enabled', True):
                                     try:
-                                        exp_date = datetime.fromisoformat(exp_str)
+                                        from managers.user_expiration import user_is_expired
-                                        if now > exp_date:
+                                        if user_is_expired(u, now=now):
-                                            logger.info(f"Subscription expired for user {u['username']} (expired at {exp_str})")
+                                            logger.info(
+                                                f"Subscription expired for user {u['username']} "
+                                                f"(expired at {u.get('expiration_date')})"
+                                            )
                                             if uid not in to_disable_uids:
                                                 to_disable_uids.append(uid)
-                                    except:
+                                    except Exception:
                                         pass
                     save_data(curr_data)
                     

managers/user_expiration.py

@@ -2,20 +2,44 @@
 
 from __future__ import annotations
 
-from datetime import datetime, timedelta
+from datetime import datetime, timedelta, timezone
-from typing import Optional
+from typing import Optional, Union
+
+
+def _parse_dt(value: Union[str, datetime, None]) -> Optional[datetime]:
+    if value is None or value == '':
+        return None
+    if isinstance(value, datetime):
+        return value
+    text = str(value).strip()
+    if not text:
+        return None
+    if text.endswith('Z'):
+        text = text[:-1] + '+00:00'
+    try:
+        return datetime.fromisoformat(text)
+    except Exception:
+        return None
+
+
+def _as_utc(dt: datetime) -> datetime:
+    """Normalize naive/aware datetimes for safe comparison."""
+    if dt.tzinfo is None:
+        # Treat naive wall time as local, then convert to UTC.
+        return dt.astimezone(timezone.utc)
+    return dt.astimezone(timezone.utc)
 
 
 def user_is_expired(user: dict, *, now: Optional[datetime] = None) -> bool:
     """True when absolute expiration_date is in the past."""
-    exp_str = user.get('expiration_date')
+    exp_date = _parse_dt(user.get('expiration_date'))
-    if not exp_str:
+    if not exp_date:
         return False
+    stamp = now if now is not None else datetime.now().astimezone()
     try:
-        exp_date = datetime.fromisoformat(str(exp_str))
+        return _as_utc(stamp) > _as_utc(exp_date)
     except Exception:
         return False
-    return (now or datetime.now()) > exp_date
 
 
 def maybe_start_user_expiration(data: dict, user_id: str, *, now: Optional[datetime] = None) -> Optional[str]:
@@ -35,8 +59,11 @@ def maybe_start_user_expiration(data: dict, user_id: str, *, now: Optional[datet
     days = int(user.get('expiration_days') or 0)
     if days <= 0:
         return None
-    stamp = now or datetime.now()
+    stamp = now if now is not None else datetime.now()
     expires = stamp + timedelta(days=days)
-    iso = expires.isoformat()
+    # Store without tz so UI/local comparisons stay consistent with manual dates
+    if expires.tzinfo is not None:
+        expires = expires.replace(tzinfo=None)
+    iso = expires.isoformat(timespec='seconds')
     user['expiration_date'] = iso
     return iso