feat(email): send plain personal email on abandoned checkout

waleedlatif1 · waleedlatif1 · commit ffec9e94eeaa · 2026-04-02T18:23:18.000-07:00
diff --git a/apps/sim/components/emails/billing/abandoned-checkout-email.tsx b/apps/sim/components/emails/billing/abandoned-checkout-email.tsx
@@ -0,0 +1,52 @@
+import { Body, Head, Html, Preview, Text } from '@react-email/components'
+
+interface AbandonedCheckoutEmailProps {
+  userName?: string
+}
+
+const styles = {
+  body: {
+    fontFamily: '-apple-system, BlinkMacSystemFont, "Segoe UI", sans-serif',
+    backgroundColor: '#ffffff',
+    margin: '0',
+    padding: '0',
+  },
+  container: {
+    maxWidth: '560px',
+    margin: '40px auto',
+    padding: '0 24px',
+  },
+  p: {
+    fontSize: '15px',
+    lineHeight: '1.6',
+    color: '#1a1a1a',
+    margin: '0 0 16px',
+  },
+} as const
+
+export function AbandonedCheckoutEmail({ userName }: AbandonedCheckoutEmailProps) {
+  return (
+    <Html>
+      <Head />
+      <Preview>Quick question</Preview>
+      <Body style={styles.body}>
+        <div style={styles.container}>
+          <Text style={styles.p}>{userName ? `Hi ${userName},` : 'Hi,'}</Text>
+          <Text style={styles.p}>
+            I saw that you tried to upgrade your Sim plan but didn&apos;t end up completing it.
+          </Text>
+          <Text style={styles.p}>
+            Did you run into an issue, or did you have a question? Here to help.
+          </Text>
+          <Text style={styles.p}>
+            — Emir
+            <br />
+            Founder, Sim
+          </Text>
+        </div>
+      </Body>
+    </Html>
+  )
+}
+
+export default AbandonedCheckoutEmail
diff --git a/apps/sim/components/emails/billing/index.ts b/apps/sim/components/emails/billing/index.ts
@@ -1,3 +1,4 @@
+export { AbandonedCheckoutEmail } from './abandoned-checkout-email'
 export { CreditPurchaseEmail } from './credit-purchase-email'
 export { EnterpriseSubscriptionEmail } from './enterprise-subscription-email'
 export { FreeTierUpgradeEmail } from './free-tier-upgrade-email'
diff --git a/apps/sim/components/emails/render.ts b/apps/sim/components/emails/render.ts
@@ -6,6 +6,7 @@ import {
   WelcomeEmail,
 } from '@/components/emails/auth'
 import {
+  AbandonedCheckoutEmail,
   CreditPurchaseEmail,
   EnterpriseSubscriptionEmail,
   FreeTierUpgradeEmail,
@@ -168,6 +169,10 @@ export async function renderOnboardingFollowupEmail(userName?: string): Promise<
   return await render(OnboardingFollowupEmail({ userName }))
 }
 
+export async function renderAbandonedCheckoutEmail(userName?: string): Promise<string> {
+  return await render(AbandonedCheckoutEmail({ userName }))
+}
+
 export async function renderCreditPurchaseEmail(params: {
   userName?: string
   amount: number
diff --git a/apps/sim/components/emails/subjects.ts b/apps/sim/components/emails/subjects.ts
@@ -16,6 +16,7 @@ export type EmailSubjectType =
   | 'plan-welcome-pro'
   | 'plan-welcome-team'
   | 'credit-purchase'
+  | 'abandoned-checkout'
   | 'onboarding-followup'
   | 'welcome'
 
@@ -56,6 +57,8 @@ export function getEmailSubject(type: EmailSubjectType): string {
       return `Your Team plan is now active on ${brandName}`
     case 'credit-purchase':
       return `Credits added to your ${brandName} account`
+    case 'abandoned-checkout':
+      return `Quick question`
     case 'onboarding-followup':
       return `Quick question about ${brandName}`
     case 'welcome':
diff --git a/apps/sim/lib/auth/auth.ts b/apps/sim/lib/auth/auth.ts
@@ -47,6 +47,7 @@ import { isOrgPlan, isTeam } from '@/lib/billing/plan-helpers'
 import { getPlans, resolvePlanFromStripeSubscription } from '@/lib/billing/plans'
 import { hasPaidSubscriptionStatus } from '@/lib/billing/subscriptions/utils'
 import { syncSeatsFromStripeQuantity } from '@/lib/billing/validation/seat-management'
+import { handleAbandonedCheckout } from '@/lib/billing/webhooks/checkout'
 import { handleChargeDispute, handleDisputeClosed } from '@/lib/billing/webhooks/disputes'
 import { handleManualEnterpriseSubscription } from '@/lib/billing/webhooks/enterprise'
 import {
@@ -2981,6 +2982,10 @@ export const auth = betterAuth({
                     await handleManualEnterpriseSubscription(event)
                     break
                   }
+                  case 'checkout.session.expired': {
+                    await handleAbandonedCheckout(event)
+                    break
+                  }
                   case 'charge.dispute.created': {
                     await handleChargeDispute(event)
                     break
diff --git a/apps/sim/lib/billing/webhooks/checkout.ts b/apps/sim/lib/billing/webhooks/checkout.ts
@@ -0,0 +1,57 @@
+import { db } from '@sim/db'
+import { user } from '@sim/db/schema'
+import { createLogger } from '@sim/logger'
+import { eq } from 'drizzle-orm'
+import type Stripe from 'stripe'
+import { getEmailSubject, renderAbandonedCheckoutEmail } from '@/components/emails'
+import { sendEmail } from '@/lib/messaging/email/mailer'
+import { getPersonalEmailFrom } from '@/lib/messaging/email/utils'
+
+const logger = createLogger('CheckoutWebhooks')
+
+/**
+ * Handles checkout.session.expired — fires when a user starts an upgrade but doesn't complete it.
+ * Sends a plain personal email to check in and offer help.
+ */
+export async function handleAbandonedCheckout(event: Stripe.Event): Promise<void> {
+  const session = event.data.object as Stripe.Checkout.Session
+
+  const customerId = typeof session.customer === 'string' ? session.customer : session.customer?.id
+  if (!customerId) {
+    logger.warn('[handleAbandonedCheckout] No customer ID on expired session', {
+      sessionId: session.id,
+    })
+    return
+  }
+
+  const [userData] = await db
+    .select({ id: user.id, email: user.email, name: user.name })
+    .from(user)
+    .where(eq(user.stripeCustomerId, customerId))
+    .limit(1)
+
+  if (!userData?.email) {
+    logger.warn('[handleAbandonedCheckout] No user found for Stripe customer', {
+      customerId,
+      sessionId: session.id,
+    })
+    return
+  }
+
+  const { from, replyTo } = getPersonalEmailFrom()
+  const html = await renderAbandonedCheckoutEmail(userData.name || undefined)
+
+  await sendEmail({
+    to: userData.email,
+    subject: getEmailSubject('abandoned-checkout'),
+    html,
+    from,
+    replyTo,
+    emailType: 'transactional',
+  })
+
+  logger.info('[handleAbandonedCheckout] Sent abandoned checkout email', {
+    userId: userData.id,
+    sessionId: session.id,
+  })
+}

Original file line number	Diff line number	Diff line change
`@@ -1,3 +1,4 @@`
	`1`	`+export { AbandonedCheckoutEmail } from './abandoned-checkout-email'`
`1`	`2`	`export { CreditPurchaseEmail } from './credit-purchase-email'`
`2`	`3`	`export { EnterpriseSubscriptionEmail } from './enterprise-subscription-email'`
`3`	`4`	`export { FreeTierUpgradeEmail } from './free-tier-upgrade-email'`