fix(billing): resolve reporting windows through the canonical period resolver

The close paths now ask resolveSubscriptionUsagePeriod whether a
subscription derives its windows from a reporting anchor instead of
re-checking metadata shape locally, so a malformed hand-edited anchor that
the resolver rejects (falling back to Stripe bounds) books its
Stripe-stamped ledger rows normally instead of skipping bookkeeping.

Co-Authored-By: Claude Opus 5 (1M context) <noreply@anthropic.com>

Author: icecrasher321

apps/sim/lib/billing/cycle-close.test.ts

@@ -12,6 +12,7 @@ const {
   mockEnqueueOutboxEvent,
   mockGetPlanPricing,
   mockGetPlanTierDollars,
+  mockResolveSubscriptionUsagePeriod,
   mockIsEnterprise,
   mockIsFree,
   mockRecordAudit,
@@ -24,6 +25,7 @@ const {
   mockEnqueueOutboxEvent: vi.fn(),
   mockGetPlanPricing: vi.fn(),
   mockGetPlanTierDollars: vi.fn(),
+  mockResolveSubscriptionUsagePeriod: vi.fn(),
   mockIsEnterprise: vi.fn(),
   mockIsFree: vi.fn(),
   mockRecordAudit: vi.fn(),
@@ -42,7 +44,7 @@ vi.mock('@/lib/billing/core/billing', () => ({
 }))
 
 vi.mock('@/lib/billing/core/reporting-period', () => ({
-  ENTERPRISE_REPORTING_PERIOD_ANCHOR_METADATA_KEY: 'reportingPeriodAnchorDate',
+  resolveSubscriptionUsagePeriod: mockResolveSubscriptionUsagePeriod,
 }))
 
 vi.mock('@/lib/billing/core/usage-log', () => ({
@@ -141,6 +143,7 @@ describe('closeElapsedBillingPeriod', () => {
     mockIsSubscriptionOrgScoped.mockResolvedValue(true)
     mockIsEnterprise.mockReturnValue(false)
     mockIsFree.mockReturnValue(false)
+    mockResolveSubscriptionUsagePeriod.mockReturnValue(null)
     mockGetPlanTierDollars.mockReturnValue(40)
     mockGetPlanPricing.mockReturnValue({ basePrice: 40 })
     mockComputeDailyRefreshConsumed.mockResolvedValue(0)
@@ -364,6 +367,7 @@ describe('closeElapsedBillingPeriod', () => {
 
   it('only advances the marker for enterprise orgs on reporting anchors', async () => {
     mockIsEnterprise.mockReturnValue(true)
+    mockResolveSubscriptionUsagePeriod.mockReturnValue({ source: 'reporting' })
 
     const result = await closeElapsedBillingPeriod(
       subRow({ plan: 'enterprise', metadata: { reportingPeriodAnchorDate: '2026-05-01' } })
@@ -400,6 +404,7 @@ describe('writeFinalPeriodBookkeeping', () => {
     resetDbChainMock()
     mockIsSubscriptionOrgScoped.mockResolvedValue(true)
     mockIsEnterprise.mockReturnValue(false)
+    mockResolveSubscriptionUsagePeriod.mockReturnValue(null)
     mockGetStampedPeriodRangeUsageCostByUser.mockResolvedValue(new Map([['owner-1', 25]]))
     dbChainMockFns.returning.mockResolvedValue([{ id: 'sub-1' }])
   })
@@ -428,6 +433,7 @@ describe('writeFinalPeriodBookkeeping', () => {
 
   it('only claims the marker for reporting-anchor enterprise subscriptions', async () => {
     mockIsEnterprise.mockReturnValue(true)
+    mockResolveSubscriptionUsagePeriod.mockReturnValue({ source: 'reporting' })
 
     await writeFinalPeriodBookkeeping({
       id: 'sub-1',

apps/sim/lib/billing/cycle-close.ts

@@ -9,11 +9,10 @@ import {
 } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
 import { getErrorMessage } from '@sim/utils/errors'
-import { isRecordLike } from '@sim/utils/object'
 import { and, eq, inArray, isNull, lt, or, sql } from 'drizzle-orm'
 import { BILLING_LOCK_TIMEOUT_MS } from '@/lib/billing/constants'
 import { computeOrgOverageAmount, isSubscriptionOrgScoped } from '@/lib/billing/core/billing'
-import { ENTERPRISE_REPORTING_PERIOD_ANCHOR_METADATA_KEY } from '@/lib/billing/core/reporting-period'
+import { resolveSubscriptionUsagePeriod } from '@/lib/billing/core/reporting-period'
 import {
   COPILOT_USAGE_SOURCES,
   getStampedPeriodRangeUsageCostByUser,
@@ -82,12 +81,21 @@ function rosterSignature(rows: { userId: string; role: string }[]): string {
     .join('|')
 }
 
-function hasEnterpriseReportingAnchor(sub: { plan: string | null; metadata?: unknown }): boolean {
-  return (
-    isEnterprise(sub.plan) &&
-    isRecordLike(sub.metadata) &&
-    typeof sub.metadata[ENTERPRISE_REPORTING_PERIOD_ANCHOR_METADATA_KEY] === 'string'
-  )
+/**
+ * Whether this subscription's usage windows derive from an enterprise
+ * reporting anchor. Asks the same resolver the usage math uses, so a
+ * malformed anchor (hand-edited Stripe metadata) that the resolver rejects —
+ * falling back to Stripe bounds — is treated identically here: the ledger
+ * rows are stamped with Stripe windows, and the close books them normally.
+ */
+function usesReportingWindows(sub: {
+  plan?: string | null
+  billingInterval?: string | null
+  metadata?: unknown
+  periodStart?: Date | null
+  periodEnd?: Date | null
+}): boolean {
+  return resolveSubscriptionUsagePeriod(sub)?.source === 'reporting'
 }
 
 /**
@@ -260,7 +268,7 @@ export async function closeElapsedBillingPeriod(sub: SubscriptionRow): Promise<C
   const closedRange = { from: closeFrom, to: periodStart }
 
   const enterprise = isEnterprise(sub.plan)
-  if (enterprise && hasEnterpriseReportingAnchor(sub)) {
+  if (enterprise && usesReportingWindows(sub)) {
     // Reporting-anchor orgs derive every usage window live from the anchor;
     // there is nothing to bill or book here. Advance the marker so the sweep
     // stays quiet.
@@ -611,7 +619,7 @@ export async function writeFinalPeriodBookkeeping(sub: {
   if (!sub.periodStart) return
   const periodStart = sub.periodStart
 
-  if (hasEnterpriseReportingAnchor(sub)) {
+  if (usesReportingWindows(sub)) {
     await db.transaction(async (tx) => claimCloseMarker(tx, sub.id, periodStart))
     return
   }