improvement(email): reply-to help@sim.ai for lifecycle and billing emails (#5487)

* improvement(email): reply-to help@sim.ai for lifecycle and billing emails

- onboarding follow-up (5-day), payment-failed, and abandoned-checkout emails now reply-to the shared help inbox instead of a personal address
- added getHelpEmailAddress() and reused it in the help route to remove the duplicated inline expression

* fix(email): address Greptile review feedback

- add a sendEmail assertion locking in the payment-failure email's replyTo
- clarify getPersonalEmailFrom() JSDoc so it doesn't overstate replyTo's scope

apps/sim/app/api/help/route.ts

@@ -4,12 +4,10 @@ import { renderHelpConfirmationEmail } from '@/components/emails'
 import { helpFormBodySchema } from '@/lib/api/contracts/common'
 import { validationErrorResponse } from '@/lib/api/server'
 import { getSession } from '@/lib/auth'
-import { env } from '@/lib/core/config/env'
 import { generateRequestId } from '@/lib/core/utils/request'
-import { getEmailDomain } from '@/lib/core/utils/urls'
 import { withRouteHandler } from '@/lib/core/utils/with-route-handler'
 import { sendEmail } from '@/lib/messaging/email/mailer'
-import { getFromEmailAddress } from '@/lib/messaging/email/utils'
+import { getFromEmailAddress, getHelpEmailAddress } from '@/lib/messaging/email/utils'
 
 const logger = createLogger('HelpAPI')
 
@@ -86,7 +84,7 @@ ${message}
     }
 
     const emailResult = await sendEmail({
-      to: [`help@${env.EMAIL_DOMAIN || getEmailDomain()}`],
+      to: [getHelpEmailAddress()],
       subject: `[${type.toUpperCase()}] ${subject}`,
       text: emailText,
       from: getFromEmailAddress(),
@@ -118,7 +116,7 @@ ${message}
         subject: `Your ${type} request has been received: ${subject}`,
         html: confirmationHtml,
         from: getFromEmailAddress(),
-        replyTo: `help@${env.EMAIL_DOMAIN || getEmailDomain()}`,
+        replyTo: getHelpEmailAddress(),
         emailType: 'transactional',
       })
     } catch (err) {

apps/sim/background/lifecycle-email.ts

@@ -7,7 +7,7 @@ import { getEmailSubject, renderOnboardingFollowupEmail } from '@/components/ema
 import { getHighestPrioritySubscription } from '@/lib/billing/core/subscription'
 import { checkEnterprisePlan } from '@/lib/billing/subscriptions/utils'
 import { sendEmail } from '@/lib/messaging/email/mailer'
-import { getPersonalEmailFrom } from '@/lib/messaging/email/utils'
+import { getHelpEmailAddress, getPersonalEmailFrom } from '@/lib/messaging/email/utils'
 import { LIFECYCLE_EMAIL_TASK_ID, type LifecycleEmailType } from '@/lib/messaging/lifecycle'
 
 const logger = createLogger('LifecycleEmail')
@@ -31,7 +31,8 @@ async function sendLifecycleEmail({ userId, type }: LifecycleEmailParams): Promi
     return
   }
 
-  const { from, replyTo } = getPersonalEmailFrom()
+  const { from } = getPersonalEmailFrom()
+  const replyTo = getHelpEmailAddress()
 
   let html: string
 

apps/sim/lib/billing/webhooks/checkout.ts

@@ -6,7 +6,7 @@ import type Stripe from 'stripe'
 import { getEmailSubject, renderAbandonedCheckoutEmail } from '@/components/emails'
 import { isProPlan } from '@/lib/billing/core/subscription'
 import { sendEmail } from '@/lib/messaging/email/mailer'
-import { getPersonalEmailFrom } from '@/lib/messaging/email/utils'
+import { getHelpEmailAddress, getPersonalEmailFrom } from '@/lib/messaging/email/utils'
 
 const logger = createLogger('CheckoutWebhooks')
 
@@ -42,7 +42,8 @@ export async function handleAbandonedCheckout(event: Stripe.Event): Promise<void
   const alreadySubscribed = await isProPlan(userData.id)
   if (alreadySubscribed) return
 
-  const { from, replyTo } = getPersonalEmailFrom()
+  const { from } = getPersonalEmailFrom()
+  const replyTo = getHelpEmailAddress()
   const html = await renderAbandonedCheckoutEmail(userData.name || undefined)
 
   await sendEmail({

apps/sim/lib/billing/webhooks/invoices.test.ts

@@ -94,6 +94,7 @@ vi.mock('@/lib/messaging/email/utils', () => ({
     from: 'billing@sim.test',
     replyTo: 'support@sim.test',
   })),
+  getHelpEmailAddress: vi.fn(() => 'help@sim.test'),
 }))
 
 vi.mock('@/lib/messaging/email/validation', () => ({
@@ -109,6 +110,7 @@ import {
   handleInvoicePaymentSucceeded,
   resetUsageForSubscription,
 } from '@/lib/billing/webhooks/invoices'
+import { sendEmail } from '@/lib/messaging/email/mailer'
 
 interface SelectResponse {
   limitResult?: unknown
@@ -194,6 +196,49 @@ describe('invoice billing recovery', () => {
     expect(mockUnblockOrgMembers).not.toHaveBeenCalled()
   })
 
+  it('sends the payment-failure email with the shared help inbox as reply-to', async () => {
+    queueSelectResponse({
+      limitResult: [
+        {
+          id: 'sub-db-1',
+          plan: 'team_8000',
+          referenceId: 'org-1',
+          stripeSubscriptionId: 'sub_stripe_1',
+        },
+      ],
+    })
+    queueSelectResponse({
+      whereResult: [{ userId: 'owner-1', role: 'owner' }],
+    })
+    queueSelectResponse({
+      whereResult: [{ email: 'owner@sim.test', name: 'Owner' }],
+    })
+
+    await handleInvoicePaymentFailed(
+      createInvoiceEvent('invoice.payment_failed', {
+        amount_due: 3582,
+        attempt_count: 1,
+        customer: 'cus_123',
+        customer_email: 'owner@sim.test',
+        hosted_invoice_url: 'https://stripe.test/invoices/in_123',
+        id: 'in_123',
+        metadata: {
+          billingPeriod: '2026-04',
+          subscriptionId: 'sub_stripe_1',
+          type: 'overage_threshold_billing_org',
+        },
+      })
+    )
+
+    expect(sendEmail).toHaveBeenCalledWith(
+      expect.objectContaining({
+        to: 'owner@sim.test',
+        from: 'billing@sim.test',
+        replyTo: 'help@sim.test',
+      })
+    )
+  })
+
   it('unblocks org members when the matching metadata-backed invoice payment succeeds', async () => {
     queueSelectResponse({
       limitResult: [

apps/sim/lib/billing/webhooks/invoices.ts

@@ -29,7 +29,7 @@ import { toDecimal, toNumber } from '@/lib/billing/utils/decimal'
 import { stripeWebhookIdempotency } from '@/lib/billing/webhooks/idempotency'
 import { getBaseUrl } from '@/lib/core/utils/urls'
 import { sendEmail } from '@/lib/messaging/email/mailer'
-import { getPersonalEmailFrom } from '@/lib/messaging/email/utils'
+import { getHelpEmailAddress, getPersonalEmailFrom } from '@/lib/messaging/email/utils'
 import { quickValidateEmail } from '@/lib/messaging/email/validation'
 
 const logger = createLogger('StripeInvoiceWebhooks')
@@ -337,7 +337,8 @@ async function sendPaymentFailureEmails(
           })
         )
 
-        const { from, replyTo } = getPersonalEmailFrom()
+        const { from } = getPersonalEmailFrom()
+        const replyTo = getHelpEmailAddress()
         await sendEmail({
           to: userToNotify.email,
           subject: 'Payment Failed - Action Required',

apps/sim/lib/messaging/email/utils.ts

@@ -35,7 +35,8 @@ export function extractEmailFromAddress(fromAddress: string): string | undefined
 }
 
 /**
- * Get the personal email from address and reply-to
+ * Get the personal email from address and reply-to. Lifecycle and billing notification
+ * emails should use `getHelpEmailAddress()` for reply-to instead of the value returned here.
  */
 export function getPersonalEmailFrom(): { from: string; replyTo: string | undefined } {
   const personalFrom = env.PERSONAL_EMAIL_FROM
@@ -50,3 +51,10 @@ export function getPersonalEmailFrom(): { from: string; replyTo: string | undefi
     replyTo: undefined,
   }
 }
+
+/**
+ * Get the shared help inbox address, used as reply-to so replies reach the team rather than an individual
+ */
+export function getHelpEmailAddress(): string {
+  return `help@${env.EMAIL_DOMAIN || getEmailDomain()}`
+}