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[charlietlamb]

Summary by cubic

Fixes a bug where promoting pending customer products erased the activated plan from billing and product webhooks after Stripe checkout.

Bug Fixes

• promotePendingCustomerProducts now returns an updated billing plan instead of mutating the original.
• Billing plan execution uses the returned plan, so the original plan data still feeds webhook events.

^{Written for commit db5f003. Summary will update on new commits.}

Greptile Summary

The PR preserves promoted pending products for post-checkout event generation while excluding them from database insertion during final plan execution.

• Bug fixes: Return a filtered billing-plan copy after pending products are promoted, preventing those existing records from being inserted again.
• Bug fixes: Execute deferred and Stripe-checkout billing with the filtered copy while retaining the original plan for activation webhooks and checkout rewards.
• Improvements: Extend checkout integration coverage to require both the product update and billing activation events.

Confidence Score: 5/5

The PR appears safe to merge, with the execution and webhook paths deliberately using separate billing-plan views for their respective responsibilities.

All current callers consume the filtered plan, unmatched planned inserts remain intact, and retained webhook history makes the expanded integration assertion safe from post-checkout polling races.

Important Files Changed

Filename	Overview
server/src/internal/billing/v2/execute/promotePendingCustomerProducts.ts	Returns a copy of the billing plan with successfully promoted products removed from the insertion list.
server/src/internal/billing/v2/execute/executeDeferredBillingPlan.ts	Executes deferred billing with the filtered plan while preserving the original plan for downstream event generation.
server/src/external/stripe/webhookHandlers/handleStripeCheckoutSessionCompleted/tasks/handleCheckoutSessionMetadataV2/handleCheckoutSessionMetadataV2.ts	Uses the filtered plan for checkout completion execution without erasing promoted products needed by webhooks and rewards.
server/tests/integration/billing/autumn-webhooks/billing-updated/billing-updated-attach.test.ts	Verifies that completed checkout emits both product-update and billing-activation events.

Sequence Diagram

sequenceDiagram
  participant Stripe
  participant Checkout as Checkout handler
  participant Promote as Pending-product promotion
  participant Execute as Billing-plan execution
  participant Events as Webhook delivery
  Stripe->>Checkout: Checkout completed
  Checkout->>Promote: Promote pending products
  Promote-->>Checkout: Return plan excluding promoted inserts
  Checkout->>Execute: Execute filtered plan
  Execute-->>Checkout: Persist remaining billing changes
  Checkout->>Events: Emit product and billing updates from original plan

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_{Reviews (1): Last reviewed commit: "Merge pull request #3214 from useautumn/..." | Re-trigger Greptile}

Context used:

• Knowledge Base — Billing lifecycle and payment flows
• Knowledge Base — Webhook contracts and delivery events