Why Aren’t Stripe Entitlements Updated After Trial Expiration?

Below is a summary addressing your questions based on Stripe’s documented behavior for entitlements and subscriptions:

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1. Will the entitlements be updated at a later time, or is this expected behavior?

Based on current Stripe behavior, it appears that entitlements are only recalculated (and the corresponding webhook event fired) during certain lifecycle changes. In your case, the trial expiration did not automatically trigger an entitlement summary update—even though subscription status events (like a pause) were sent. This is expected behavior: the entitlement summary is updated when changes to the active subscription that affect feature access occur, and not every subscription status change (such as a trial ending or a pause) necessarily triggers an entitlement update.

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2. What is the proper way to handle trials in my case?

For trial periods, it’s recommended to:

• Track both subscription events and entitlement events: In addition to listening for entitlement changes (via entitlements.active_entitlement_summary.updated), continue handling subscription events like customer.subscription.updated, paused, or even cancellation events.
• Implement custom logic: Use the subscription status updates (e.g., the transition out of trial or changes to an active subscription) to adjust your internal records. This ensures that if an entitlement event isn’t fired (as in your trial expiration scenario), your system still synchronizes and revokes access when appropriate.

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3. Should we expect entitlements.active_entitlement_summary.updated events to fire when a subscription is canceled, paused, or deleted?

Not necessarily. Only subscription lifecycle changes that affect a customer’s active access to a feature will trigger an entitlement update event. In some cases (for example, when a trial ends and the subscription is paused or canceled), you may receive subscription-related events without a corresponding entitlement update. That means you should plan on handling subscription changes (via events like customer.subscription.updated or customer.subscription.paused) alongside entitlement events.

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4. If we need to sync the subscription status in a separate table anyways, does this not defeat the point of “Simplifying your billing integration”?

Not at all. The entitlements feature is designed to simplify the authorization of feature access based on subscription status. However, if your application requires more granular control or immediate revocation (and additional system-specific logic), maintaining an internal subscription or entitlement status table is a common—and often necessary—pattern. In practice, many integrations combine Stripe’s entitlement events with their own subscription status tracking to ensure that business logic (especially regarding trials, pauses, or cancellations) is handled precisely as needed.

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Final Recommendations

• Monitor multiple event types: Combine entitlement events with subscription state change events to catch changes that may not trigger an entitlement update.
• Implement custom business logic: Use your internal tables and webhook processing to enforce access rules. For example, if you see a customer.subscription.paused event and no corresponding entitlement update, update your system to revoke the feature access.
• Review Stripe’s guidelines: As per the documentation, “as long as a customer maintains an active subscription for a feature, they retain an active entitlement.” In cases where the active subscription is altered (paused, canceled), your system must independently reconcile these changes.

By handling both sets of events, you ensure that your application consistently reflects the customer’s current access state even if some expected entitlement events are not fired.

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This approach is aligned with best practices in subscription management and access control when using Stripe’s Payment Links and Entitlements.