waleedlatif1 · Oct 28, 2026 · Oct 28, 2026 · Oct 28, 2026 · Oct 28, 2026 · Oct 28, 2026
diff --git a/apps/sim/lib/billing/core/usage.test.ts b/apps/sim/lib/billing/core/usage.test.ts
@@ -59,6 +59,10 @@ vi.mock('@/lib/users/deleted-identity', () => ({
   userHasDeletedAccountIdentity: mockUserHasDeletedAccountIdentity,
 }))
 
+vi.mock('@/lib/users/gmail-alias', () => ({
+  userHasGmailAliasAccount: vi.fn(async () => false),
+}))
+
 import {
   ensureUserStatsExists,
   getUserUsageLimit,

diff --git a/apps/sim/lib/billing/core/usage.ts b/apps/sim/lib/billing/core/usage.ts
@@ -50,6 +50,7 @@ import {
   isDeletedAccountIdentity,
   userHasDeletedAccountIdentity,
 } from '@/lib/users/deleted-identity'
+import { userHasGmailAliasAccount } from '@/lib/users/gmail-alias'
 
 const logger = createLogger('UsageManagement')
 
@@ -191,6 +192,22 @@ function calculateOrgUsageLimit(
  */
 const usersCreatedInAuthRequest = new WeakMap<object, string>()
 
+/**
+ * Whether a new user's identity already had the free allowance: its email or a
+ * linked sign-in (with `includeSignIns`) belonged to a recently deleted account,
+ * or another account already holds its Gmail inbox.
+ */
+async function identityHadFreeAllowance(
+  userId: string,
+  { includeSignIns }: { includeSignIns: boolean },
+  executor: DbOrTx = db
+): Promise<boolean> {
+  return (
+    (await userHasDeletedAccountIdentity(userId, { includeSignIns }, executor)) ||
+    (await userHasGmailAliasAccount(userId, executor))
+  )
+}
+
 function isUserCreatedInAuthRequest(
   userId: string,
   authRequest: object | null | undefined
@@ -202,20 +219,18 @@ function isUserCreatedInAuthRequest(
  * Handle new user setup when they join the platform.
  * Creates the userStats record with the free allowance, which is zero when the
  * user's email or an already-linked social sign-in belongs to an account
- * deleted within the retention window. Every user Better Auth creates comes
- * through here, including SCIM- and SSO-provisioned users, so their email is
- * always checked at creation.
+ * deleted within the retention window, or when another account holds its Gmail
+ * inbox. Every user Better Auth creates comes through here, including SCIM- and
+ * SSO-provisioned users, so their email is always checked at creation.
  *
  * @param authRequest Better Auth's endpoint context for the signup request, when there is one
  */
 export async function handleNewUser(userId: string, authRequest?: object | null): Promise<void> {
   if (authRequest) usersCreatedInAuthRequest.set(authRequest, userId)
   try {
-    const freeTierEligible = !(await userHasDeletedAccountIdentity(userId, {
-      includeSignIns: true,
-    }))
+    const freeTierEligible = !(await identityHadFreeAllowance(userId, { includeSignIns: true }))
     if (!freeTierEligible) {
-      logger.info('Withholding the free allowance from a returning deleted-account identity', {
+      logger.info('Withholding the free allowance from an identity that already had it', {
         userId,
       })
     }
@@ -315,7 +330,7 @@ export async function createUserStatsIfMissing(
   if (created.length === 0) return false
 
   try {
-    if (await userHasDeletedAccountIdentity(userId, { includeSignIns }, executor)) {
+    if (await identityHadFreeAllowance(userId, { includeSignIns }, executor)) {
       await forfeitFreeTierAllowance(executor, userId)
     }
   } catch (error) {
@@ -704,18 +719,18 @@ export async function checkUsageStatus(userId: string): Promise<{
 }
 
 /**
- * Withholds the free allowance from a new account found to reuse the sign-in
- * identity of a recently deleted one after its stats row was created. The flag
- * and the limit it implies commit together (a transaction on `db`, a savepoint
- * inside a caller's transaction), so a failed re-derivation can never leave the
- * account flagged but still holding the free limit; repeating the call is harmless.
+ * Withholds the free allowance from a new account found, after its stats row was
+ * created, to reuse an identity that already had it. The flag and the limit it
+ * implies commit together (a transaction on `db`, a savepoint inside a caller's
+ * transaction), so a failed re-derivation can never leave the account flagged
+ * but still holding the free limit; repeating the call is harmless.
  */
 async function forfeitFreeTierAllowance(executor: DbOrTx, userId: string): Promise<void> {
   await executor.transaction(async (tx) => {
     await tx.update(userStats).set({ freeTierEligible: false }).where(eq(userStats.userId, userId))
     await syncUsageLimitsFromSubscription(userId, tx)
   })
-  logger.info('Withheld the free allowance from a returning deleted-account identity', { userId })
+  logger.info('Withheld the free allowance from an identity that already had it', { userId })
 }
 
 /**

diff --git a/apps/sim/lib/users/gmail-alias.integration.ts b/apps/sim/lib/users/gmail-alias.integration.ts
@@ -0,0 +1,178 @@
+/**
+ * A dot, `+tag`, or `googlemail.com` variant of an existing Gmail address must not get a second
+ * free allowance. Runs against real PostgreSQL through the production signup-stats and
+ * fallback-stats paths, and checks the lookup is served by `user_gmail_mailbox_idx`.
+ */
+import { db } from '@sim/db'
+import { gmailMailbox, user, userStats } from '@sim/db/schema'
+import { authMock } from '@sim/testing/mocks/auth.mock'
+import { envFlagsMock } from '@sim/testing/mocks/env-flags.mock'
+import { generateId } from '@sim/utils/id'
+import { eq, inArray, sql } from 'drizzle-orm'
+import { afterAll, describe, expect, it, vi } from 'vitest'
+import { ensureUserStatsExists, handleNewUser } from '@/lib/billing/core/usage'
+import { getFreeTierLimit } from '@/lib/billing/subscriptions/utils'
+
+vi.mock('@/lib/core/config/env-flags', () => ({
+  ...envFlagsMock,
+  isHosted: true,
+  isBillingEnabled: true,
+}))
+vi.mock('@/lib/auth', () => authMock)
+
+const userIds: string[] = []
+
+async function insertUser(
+  email: string,
+  { banned = false, emailVerified = true, createdAt = new Date() } = {}
+): Promise<string> {
+  const id = generateId()
+  userIds.push(id)
+  await db.insert(user).values({
+    id,
+    name: 'Gmail alias fixture',
+    email,
+    emailVerified,
+    banned,
+    createdAt,
+    updatedAt: createdAt,
+  })
+  return id
+}
+
+async function signUp(
+  email: string,
+  options?: { banned?: boolean; emailVerified?: boolean }
+): Promise<string> {
+  const id = await insertUser(email, options)
+  await handleNewUser(id, {})
+  return id
+}
+
+async function statsOf(userId: string) {
+  const [row] = await db
+    .select({
+      freeTierEligible: userStats.freeTierEligible,
+      currentUsageLimit: userStats.currentUsageLimit,
+    })
+    .from(userStats)
+    .where(eq(userStats.userId, userId))
+  return { freeTierEligible: row?.freeTierEligible, limit: Number(row?.currentUsageLimit) }
+}
+
+/** A Gmail local part no other test run can collide with. */
+function uniqueLocalPart(): string {
+  return `alias${generateId().replaceAll('-', '')}`
+}
+
+afterAll(async () => {
+  if (userIds.length) await db.delete(user).where(inArray(user.id, userIds))
+})
+
+describe('Gmail inboxes and the free allowance', () => {
+  it('withholds the allowance from dot, +tag, and googlemail variants of a live account', async () => {
+    const local = uniqueLocalPart()
+    const original = await signUp(`${local}@gmail.com`)
+
+    const dotted = await signUp(`${local.slice(0, 4)}.${local.slice(4)}@gmail.com`)
+    const tagged = await signUp(`${local}+farm@gmail.com`)
+    const googlemail = await signUp(`${local.toUpperCase()}@GoogleMail.com`)
+
+    expect(await statsOf(original)).toEqual({ freeTierEligible: true, limit: getFreeTierLimit() })
+    for (const variant of [dotted, tagged, googlemail]) {
+      expect(await statsOf(variant)).toEqual({ freeTierEligible: false, limit: 0 })
+    }
+  })
+
+  it('withholds it when the inbox belongs to a banned account', async () => {
+    const local = uniqueLocalPart()
+    await signUp(`${local}@gmail.com`, { banned: true })
+
+    const returning = await signUp(`${local}+again@gmail.com`)
+
+    expect(await statsOf(returning)).toEqual({ freeTierEligible: false, limit: 0 })
+  })
+
+  it('withholds it from aliases registered before any of them verified the inbox', async () => {
+    const local = uniqueLocalPart()
+    const first = await signUp(`${local}@gmail.com`, { emailVerified: false })
+    const second = await signUp(`${local}+two@gmail.com`, { emailVerified: false })
+    await db
+      .update(user)
+      .set({ emailVerified: true })
+      .where(inArray(user.id, [first, second]))
+
+    const third = await signUp(`${local.slice(0, 5)}.${local.slice(5)}@gmail.com`)
+
+    expect(await statsOf(first)).toEqual({ freeTierEligible: true, limit: getFreeTierLimit() })
+    expect(await statsOf(second)).toEqual({ freeTierEligible: false, limit: 0 })
+    expect(await statsOf(third)).toEqual({ freeTierEligible: false, limit: 0 })
+  })
+
+  it('grants it to a different Gmail inbox and never folds addresses outside Gmail', async () => {
+    const local = uniqueLocalPart()
+    await signUp(`${local}@gmail.com`)
+    await signUp(`${local}+one@gmail-alias.test`)
+
+    const otherInbox = await signUp(`${local}x@gmail.com`)
+    const otherDomain = await signUp(`${local}@gmail-alias.test`)
+
+    expect(await statsOf(otherInbox)).toEqual({ freeTierEligible: true, limit: getFreeTierLimit() })
+    expect(await statsOf(otherDomain)).toEqual({
+      freeTierEligible: true,
+      limit: getFreeTierLimit(),
+    })
+  })
+
+  it('withholds it from a stats row the fallback creates after signup failed to', async () => {
+    const local = uniqueLocalPart()
+    await signUp(`${local}@gmail.com`)
+    const alias = await insertUser(`${local.slice(0, 3)}.${local.slice(3)}@gmail.com`)
+
+    await ensureUserStatsExists(alias)
+
+    expect(await statsOf(alias)).toEqual({ freeTierEligible: false, limit: 0 })
+  })
+
+  it('keeps the allowance with the inbox’s first account when its stats row comes after an alias’s', async () => {
+    const local = uniqueLocalPart()
+    const original = await insertUser(`${local}@gmail.com`, {
+      createdAt: new Date(Date.now() - 60_000),
+    })
+    const alias = await signUp(`${local}+later@gmail.com`)
+
+    await ensureUserStatsExists(original)
+
+    expect(await statsOf(original)).toEqual({ freeTierEligible: true, limit: getFreeTierLimit() })
+    expect(await statsOf(alias)).toEqual({ freeTierEligible: false, limit: 0 })
+  })
+
+  it('withholds from exactly one of two accounts created at the same instant', async () => {
+    const local = uniqueLocalPart()
+    const createdAt = new Date()
+    const first = await insertUser(`${local}@gmail.com`, { createdAt })
+    const second = await insertUser(`${local.slice(0, 2)}.${local.slice(2)}@gmail.com`, {
+      createdAt,
+    })
+
+    await ensureUserStatsExists(first)
+    await ensureUserStatsExists(second)
+
+    const eligible = [await statsOf(first), await statsOf(second)].map(
+      (stats) => stats.freeTierEligible
+    )
+    expect(eligible.sort()).toEqual([false, true])
+  })
+
+  it('finds the inbox through user_gmail_mailbox_idx rather than a scan of user', async () => {
+    const plan = await db.transaction(async (tx) => {
+      await tx.execute(sql`SET LOCAL enable_seqscan = off`)
+      const rows = await tx.execute<{ 'QUERY PLAN': string }>(
+        sql`EXPLAIN SELECT ${user.id} FROM ${user} WHERE ${gmailMailbox(user.email)} = ${`${uniqueLocalPart()}@gmail.com`} LIMIT 1`
+      )
+      return rows.map((row) => row['QUERY PLAN']).join('\n')
+    })
+
+    expect(plan).toContain('user_gmail_mailbox_idx')
+  })
+})
diff --git a/apps/sim/lib/users/gmail-alias.ts b/apps/sim/lib/users/gmail-alias.ts
@@ -0,0 +1,67 @@
+import { db } from '@sim/db'
+import { gmailMailbox, user } from '@sim/db/schema'
+import { createLogger } from '@sim/logger'
+import { and, eq, lt, or, sql } from 'drizzle-orm'
+import { isBillingEnabled } from '@/lib/core/config/env-flags'
+import type { DbOrTx } from '@/lib/db/types'
+
+/**
+ * One free allowance per Gmail inbox. Gmail delivers every dot and `+tag`
+ * variant of an address, and its `googlemail.com` twin, to the same inbox, so
+ * without this one person could register `a.b@gmail.com`, `ab+1@gmail.com`, …
+ * for a fresh allowance each time. The later account is created normally but
+ * without the free allowance, like a returning deleted-account identity.
+ *
+ * Only meaningful where billing is enabled.
+ */
+
+const logger = createLogger('GmailAlias')
+
+/**
+ * Whether an earlier account, banned or not, already holds the Gmail inbox this
+ * user's address delivers to. Only an account created before this one counts
+ * (the id breaks a creation-time tie), so the inbox's first account keeps the
+ * allowance however late its own stats row is created. The earlier account
+ * counts whether or not it verified the address: the allowance is granted at
+ * signup, before verification, and where verification is off a password
+ * account never verifies, so a verified-only rule would let every alias
+ * registered unverified keep its allowance. Pass the caller's transaction as
+ * `executor` to read on it; the read then runs in a savepoint, so a failed
+ * lookup never aborts that transaction. Fails open: a lookup error returns
+ * `false` and is logged, because refusing a legitimate person's allowance is
+ * worse than one missed match.
+ */
+export async function userHasGmailAliasAccount(
+  userId: string,
+  executor: DbOrTx = db
+): Promise<boolean> {
+  if (!isBillingEnabled) return false
+  const read = async (reader: DbOrTx) => {
+    const [self] = await reader
+      .select({ mailbox: gmailMailbox(user.email), createdAt: user.createdAt })
+      .from(user)
+      .where(eq(user.id, userId))
+      .limit(1)
+    if (!self?.mailbox) return false
+    const [other] = await reader
+      .select({ id: user.id })
+      .from(user)
+      .where(
+        and(
+          sql`${gmailMailbox(user.email)} = ${self.mailbox}`,
+          or(
+            lt(user.createdAt, self.createdAt),
+            and(eq(user.createdAt, self.createdAt), lt(user.id, userId))
+          )
+        )
+      )
+      .limit(1)
+    return Boolean(other)
+  }
+  try {
+    return await (executor === db ? read(db) : executor.transaction(read))
+  } catch (error) {
+    logger.error('Gmail alias lookup failed; granting the free allowance', { userId, error })
+    return false
+  }
+}
diff --git a/packages/db/migrations/0439_gmail_mailbox_index.sql b/packages/db/migrations/0439_gmail_mailbox_index.sql
@@ -0,0 +1,6 @@
+COMMIT;--> statement-breakpoint
+SET lock_timeout = 0;--> statement-breakpoint
+-- migration-safe: this new additive index has no deployed readers; remove any unjournaled prior build before rebuilding concurrently on replay.
+DROP INDEX CONCURRENTLY IF EXISTS "user_gmail_mailbox_idx";--> statement-breakpoint
+CREATE INDEX CONCURRENTLY IF NOT EXISTS "user_gmail_mailbox_idx" ON "user" USING btree ((CASE WHEN split_part(lower(btrim("email")), '@', 2) IN ('gmail.com', 'googlemail.com') THEN replace(split_part(split_part(lower(btrim("email")), '@', 1), '+', 1), '.', '') || '@gmail.com' END)) WHERE (CASE WHEN split_part(lower(btrim("user"."email")), '@', 2) IN ('gmail.com', 'googlemail.com') THEN replace(split_part(split_part(lower(btrim("user"."email")), '@', 1), '+', 1), '.', '') || '@gmail.com' END) IS NOT NULL;--> statement-breakpoint
+SET lock_timeout = '5s';