diff --git a/app/admin_model.py b/app/admin_model.py
index 7f030093..29642b22 100644
--- a/app/admin_model.py
+++ b/app/admin_model.py
@@ -117,7 +117,12 @@ def manual_upgrade(way: str, ids: [int], is_giveaway: bool):
             flash(f"Subscription extended to {manual_sub.end_at.humanize()}", "success")
             continue
 
-        if user.is_premium() and not user.in_trial():
+        # user can have manual subscription applied if their current subscription is canceled
+        if (
+            user.is_premium()
+            and not user.in_trial()
+            and not user.subscription_cancelled
+        ):
             flash(f"User {user} is already premium", "warning")
             continue
 
diff --git a/app/models.py b/app/models.py
index e9e04fe6..fdbd3a3f 100644
--- a/app/models.py
+++ b/app/models.py
@@ -487,6 +487,28 @@ class User(db.Model, ModelMixin, UserMixin, PasswordOracle):
 
         return "N/A"
 
+    @property
+    def subscription_cancelled(self) -> bool:
+        sub: Subscription = self.get_subscription()
+        if sub and sub.cancelled:
+            return True
+
+        apple_sub: AppleSubscription = AppleSubscription.get_by(user_id=self.id)
+        if apple_sub and not apple_sub.is_valid():
+            return True
+
+        manual_sub: ManualSubscription = ManualSubscription.get_by(user_id=self.id)
+        if manual_sub and not manual_sub.is_active():
+            return True
+
+        coinbase_subscription: CoinbaseSubscription = CoinbaseSubscription.get_by(
+            user_id=self.id
+        )
+        if coinbase_subscription and not coinbase_subscription.is_active():
+            return True
+
+        return False
+
     @property
     def premium_end(self) -> str:
         if self.lifetime: