diff --git a/packages/twenty-server/src/engine/core-modules/billing/services/billing-portal.workspace-service.ts b/packages/twenty-server/src/engine/core-modules/billing/services/billing-portal.workspace-service.ts
index d899763e7ec..acfbdee7eb2 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/services/billing-portal.workspace-service.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/services/billing-portal.workspace-service.ts
@@ -101,6 +101,8 @@ export class BillingPortalWorkspaceService {
         stripeCustomerId: customer?.stripeCustomerId,
         plan,
         requirePaymentMethod,
+        withTrialPeriod:
+          !isDefined(customer) || customer.billingSubscriptions.length === 0,
       });
 
     const createdBillingSubscription =
diff --git a/packages/twenty-server/src/engine/core-modules/billing/stripe/services/stripe-checkout.service.ts b/packages/twenty-server/src/engine/core-modules/billing/stripe/services/stripe-checkout.service.ts
index bce91a6ae91..41066f39cd8 100644
--- a/packages/twenty-server/src/engine/core-modules/billing/stripe/services/stripe-checkout.service.ts
+++ b/packages/twenty-server/src/engine/core-modules/billing/stripe/services/stripe-checkout.service.ts
@@ -95,6 +95,7 @@ export class StripeCheckoutService {
     stripeCustomerId,
     plan = BillingPlanKey.PRO,
     requirePaymentMethod = false,
+    withTrialPeriod,
   }: {
     user: User;
     workspace: Pick<Workspace, 'id' | 'displayName'>;
@@ -102,6 +103,7 @@ export class StripeCheckoutService {
     stripeCustomerId?: string;
     plan?: BillingPlanKey;
     requirePaymentMethod?: boolean;
+    withTrialPeriod: boolean;
   }): Promise<Stripe.Subscription> {
     if (!isDefined(stripeCustomerId)) {
       const stripeCustomer =
@@ -128,6 +130,10 @@ export class StripeCheckoutService {
         workspaceId: workspace.id,
         plan,
       },
+      ...this.getStripeSubscriptionTrialPeriodConfig(
+        withTrialPeriod,
+        requirePaymentMethod,
+      ),
       automatic_tax: { enabled: !!requirePaymentMethod },
     };