fix: preserve active Pro entitlement on stale Stripe webhooks

[richiemcilroy]

Summary

• Keep an entitled Pro subscription on the user record when an earlier checkout expires or is deleted.
• Prefer active or trialing Pro subscriptions over past-due ones and preserve the combined entitled seat quota.
• Read every Stripe subscription page before choosing the effective subscription.

Incident

An abandoned checkout's customer.subscription.updated event arrived after a paid checkout and overwrote the user's active Pro status with incomplete_expired. Two affected production accounts have been reconciled separately.

Verification

• Biome check on both touched files
• bun run test __tests__/unit/signed-baa-webhook.test.ts --silent --reporter=dot (36 passed)

[greptile-apps]

Pagination can revoke entitlement

If a customer has more than 100 subscription attempts, their entitled Pro subscription can be on a later Stripe page. This code only selects from the first 100 records, so a stale canceled or expired webhook can fall back to its own subscription and overwrite the user's active entitlement. Fetch all subscription pages before choosing the effective subscription and calculating the combined quota. The deleted-event path at lines 911–926 has the same problem.

Prompt To Fix With AI

This is a comment left during a code review.
Path: apps/web/app/api/webhooks/stripe/route.ts
Line: 778-782

Comment:
**Pagination can revoke entitlement**

If a customer has more than 100 subscription attempts, their entitled Pro subscription can be on a later Stripe page. This code only selects from the first 100 records, so a stale canceled or expired webhook can fall back to its own subscription and overwrite the user's active entitlement. Fetch all subscription pages before choosing the effective subscription and calculating the combined quota. The deleted-event path at lines 911–926 has the same problem.

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For each issue above, determine whether it is valid and should be fixed. If so, fix it directly.