diff --git a/corporate/lib/stripe.py b/corporate/lib/stripe.py
index 70cd46248a..aa4a1870d8 100644
--- a/corporate/lib/stripe.py
+++ b/corporate/lib/stripe.py
@@ -361,6 +361,10 @@ class BillingSession(ABC):
     def get_customer(self) -> Optional[Customer]:
         pass
 
+    @abstractmethod
+    def current_count_for_billed_licenses(self) -> int:
+        pass
+
     @abstractmethod
     def get_audit_log_event(self, event_type: AuditLogEventType) -> int:
         pass
@@ -617,6 +621,10 @@ class RealmBillingSession(BillingSession):
     def get_customer(self) -> Optional[Customer]:
         return get_customer_by_realm(self.realm)
 
+    @override
+    def current_count_for_billed_licenses(self) -> int:
+        return get_latest_seat_count(self.realm)
+
     @override
     def get_audit_log_event(self, event_type: AuditLogEventType) -> int:
         if event_type is AuditLogEventType.STRIPE_CUSTOMER_CREATED:
@@ -1064,7 +1072,8 @@ def process_initial_upgrade(
         else:
             # billed_licenses can be greater than licenses if users are added between the start of
             # this function (process_initial_upgrade) and now
-            billed_licenses = max(get_latest_seat_count(customer.realm), licenses)
+            current_licenses_count = billing_session.current_count_for_billed_licenses()
+            billed_licenses = max(current_licenses_count, licenses)
         plan_params = {
             "automanage_licenses": automanage_licenses,
             "charge_automatically": charge_automatically,