fix(billing): plan should be detected from stripe subscription object

[icecrasher321]

Summary

Pro to Team triggers sub update not create. Need to pick out plan from event object instead of stale db entry.

Type of Change

• Bug fix

Testing

Tested using Stripe CLI

Checklist

• Code follows project style guidelines
• Self-reviewed my changes
• Tests added/updated and passing
• No new warnings introduced
• I confirm that I have read and agree to the terms outlined in the Contributor License Agreement (CLA)

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1 Skipped Deployment

Project	Deployment	Actions	Updated (UTC)
docs	Skipped		Jan 31, 2026 0:35am

[icecrasher321]

@cursor review

[greptile-apps]

Greptile Overview

Greptile Summary

Fixed critical bug where Pro-to-Team subscription upgrades were not properly detected because they trigger Stripe subscription.updated events rather than subscription.created events. This caused the system to rely on stale database entries that hadn't been updated yet with the new plan.

Key Changes:

• Added resolvePlanFromStripeSubscription() utility to extract the authoritative plan directly from Stripe subscription objects via price ID lookup
• Modified onSubscriptionUpdate to detect Pro→Team upgrades by comparing Stripe's plan against the DB plan
• Updated onSubscriptionComplete to use Stripe-sourced plan information for consistency
• Enhanced logging throughout to track both DB plan and Stripe plan for debugging

Impact:

• Organization creation now triggers correctly when users upgrade from Pro to Team
• Seat management features activate properly for Team plan upgrades
• Prevents relying on stale database state during webhook processing

Confidence Score: 4/5

• Safe to merge with minor considerations around edge cases
• The fix correctly addresses the race condition by reading from the authoritative Stripe event object. The logic is sound and well-tested via Stripe CLI. Minor score reduction due to complexity of the fallback logic and potential edge cases with unrecognized price IDs.
• No files require special attention - both changes are straightforward

Important Files Changed

Filename	Overview
apps/sim/lib/billing/plans.ts	Added utility functions to resolve plan from Stripe subscription object
apps/sim/lib/auth/auth.ts	Fixed Pro->Team upgrade by detecting plan from Stripe event instead of stale DB entry

Sequence Diagram

sequenceDiagram
    participant User
    participant Stripe
    participant Webhook as Webhook Handler
    participant DB as Database
    participant Resolver as resolvePlanFromStripeSubscription
    participant OrgEnsure as ensureOrganizationForTeamSubscription

    Note over User,Stripe: User upgrades from Pro to Team

    User->>Stripe: Upgrade subscription
    Stripe->>Webhook: subscription.updated event
    Note over Webhook: Event contains updated Stripe subscription
    Note over DB: DB subscription.plan still shows 'pro' (stale)

    Webhook->>Resolver: resolvePlanFromStripeSubscription(stripeSubscription)
    Resolver->>Resolver: Extract priceId from subscription.items[0].price.id
    Resolver->>Resolver: getPlanByPriceId(priceId)
    Resolver-->>Webhook: {planFromStripe: 'team', isTeamPlan: true}

    Webhook->>Webhook: Detect upgrade: isTeamPlan && db.plan !== 'team'
    Note over Webhook: isUpgradeToTeam = true

    Webhook->>Webhook: Create subscriptionForOrgCreation<br/>with plan: 'team'
    Webhook->>OrgEnsure: ensureOrganizationForTeamSubscription(subscriptionForOrgCreation)
    
    OrgEnsure->>OrgEnsure: Check if subscription.plan === 'team'
    Note over OrgEnsure: Now sees 'team' instead of stale 'pro'
    
    OrgEnsure->>DB: Create organization for user
    OrgEnsure->>DB: Update subscription.referenceId to org_xxx
    OrgEnsure-->>Webhook: resolvedSubscription (with org referenceId)

    Webhook->>Webhook: Use effectivePlanForTeamFeatures = 'team'
    Webhook->>DB: syncSeatsFromStripeQuantity()
    Note over Webhook: Team features now active

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