diff --git a/src/auth/supabase_entitlement.py b/src/auth/supabase_entitlement.py
index ce516c06..0b0d9a87 100644
--- a/src/auth/supabase_entitlement.py
+++ b/src/auth/supabase_entitlement.py
@@ -218,14 +218,17 @@ class SupabaseEntitlementService:
                     response.status_code,
                 )
                 row = None
+                rows: List[Dict[str, object]] = []
             else:
                 data = response.json() if response.content else []
-                row = self._pick_latest_current_subscription(data, now=now)
+                rows = [item for item in data if isinstance(item, dict)] if isinstance(data, list) else []
+                row = self._pick_latest_current_subscription(rows, now=now)
 
             with self._sub_cache_lock:
                 self._sub_cache[user_id] = {
                     "active": bool(row),
                     "row": row,
+                    "rows": rows,
                     "ts": now_ts,
                 }
             return row
@@ -236,6 +239,7 @@ class SupabaseEntitlementService:
     def _query_active_subscription_rows(
         self,
         user_id: str,
+        bypass_cache: bool = False,
     ) -> List[Dict[str, object]]:
         if not user_id:
             return []
@@ -244,16 +248,17 @@ class SupabaseEntitlementService:
             return []
 
         now_ts = time.time()
-        with self._sub_cache_lock:
-            cached = self._sub_cache.get(user_id)
-            if cached and now_ts - float(cached.get("ts") or 0) < self.sub_cache_ttl_sec:
-                rows = cached.get("rows")
-                if isinstance(rows, list):
-                    return [row for row in rows if isinstance(row, dict)]
-                row = cached.get("row")
-                if isinstance(row, dict):
-                    return [row]
-                return []
+        if not bypass_cache:
+            with self._sub_cache_lock:
+                cached = self._sub_cache.get(user_id)
+                if cached and now_ts - float(cached.get("ts") or 0) < self.sub_cache_ttl_sec:
+                    rows = cached.get("rows")
+                    if isinstance(rows, list):
+                        return [row for row in rows if isinstance(row, dict)]
+                    row = cached.get("row")
+                    if isinstance(row, dict):
+                        return [row]
+                    return []
 
         try:
             now = datetime.now(timezone.utc)
@@ -520,10 +525,11 @@ class SupabaseEntitlementService:
         self,
         user_id: str,
         respect_requirement: bool = True,
+        bypass_cache: bool = False,
     ) -> Dict[str, object]:
         if respect_requirement and not self.require_subscription:
             return {}
-        rows = self._query_active_subscription_rows(user_id)
+        rows = self._query_active_subscription_rows(user_id, bypass_cache=bypass_cache)
         if not rows:
             return {}
 
diff --git a/tests/test_supabase_entitlement.py b/tests/test_supabase_entitlement.py
index 145e16d3..1aff5597 100644
--- a/tests/test_supabase_entitlement.py
+++ b/tests/test_supabase_entitlement.py
@@ -100,3 +100,43 @@ def test_latest_active_subscription_ignores_future_start(monkeypatch):
 
     assert result is not None
     assert result["plan_code"] == "signup_trial_3d"
+
+
+def test_subscription_window_keeps_queued_renewal_after_current_cache(monkeypatch):
+    monkeypatch.setenv("SUPABASE_URL", "https://example.supabase.co")
+    monkeypatch.setenv("SUPABASE_ANON_KEY", "anon-key")
+    monkeypatch.setenv("SUPABASE_SERVICE_ROLE_KEY", "service-role")
+
+    service = SupabaseEntitlementService()
+
+    now = datetime.now(timezone.utc)
+    current = {
+        "id": 1,
+        "user_id": "user-1",
+        "status": "active",
+        "plan_code": "pro_monthly",
+        "starts_at": (now - timedelta(days=29)).isoformat(),
+        "expires_at": (now + timedelta(days=1)).isoformat(),
+    }
+    queued = {
+        "id": 2,
+        "user_id": "user-1",
+        "status": "active",
+        "plan_code": "pro_monthly",
+        "starts_at": (now + timedelta(days=1)).isoformat(),
+        "expires_at": (now + timedelta(days=31)).isoformat(),
+    }
+
+    def _fake_get(url, headers=None, params=None, timeout=None):
+        return _Response(200, [queued, current])
+
+    monkeypatch.setattr(entitlement_module.requests, "get", _fake_get)
+
+    assert service._query_latest_active_subscription("user-1") == current
+
+    window = service.get_subscription_window("user-1", respect_requirement=False)
+
+    assert window["current"] == current
+    assert window["total_expires_at"] == queued["expires_at"]
+    assert window["queued_days"] == 30
+    assert window["queued_count"] == 1
diff --git a/web/routes.py b/web/routes.py
index e45173a1..dd5ae31a 100644
--- a/web/routes.py
+++ b/web/routes.py
@@ -1083,6 +1083,7 @@ async def ops_memberships(request: Request, limit: int = 200):
         subscription_window = SUPABASE_ENTITLEMENT.get_subscription_window(
             user_id,
             respect_requirement=False,
+            bypass_cache=True,
         )
         current_expires_at = item.get("expires_at")
         total_expires_at = (