diff --git a/packages/twenty-server/src/engine/core-modules/billing/commands/billing-add-workflow-subscription-item.command.ts b/packages/twenty-server/src/engine/core-modules/billing/commands/billing-add-workflow-subscription-item.command.ts
index bb2cb01a9..d1ba96112 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/commands/billing-add-workflow-subscription-item.command.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/commands/billing-add-workflow-subscription-item.command.ts
@@ -81,6 +81,17 @@ export class BillingAddWorkflowSubscriptionItemCommand extends ActiveOrSuspended
     }
 
     if (!options.dryRun) {
+      await this.stripeSubscriptionService.updateSubscription(
+        subscription.stripeSubscriptionId,
+        {
+          trial_settings: {
+            end_behavior: {
+              missing_payment_method: 'create_invoice',
+            },
+          },
+        },
+      );
+
       await this.stripeSubscriptionItemService.createSubscriptionItem(
         subscription.stripeSubscriptionId,
         associatedWorkflowMeteredPrice.stripePriceId,