Stripe Production Engineering

Stripe Production Engineering

Complete methodology for building, scaling, and operating production Stripe payment systems. From first checkout to enterprise billing at scale.

Quick Health Check

Run through these 8 signals. Score 1 point each. Below 5 = stop and fix.

1. ✅ Webhook endpoint verified and idempotent
2. ✅ All API calls use idempotency keys
3. ✅ Customer portal enabled for self-service
4. ✅ Stripe Tax or manual tax collection configured
5. ✅ Failed payment retry logic with dunning emails
6. ✅ PCI compliance questionnaire completed (SAQ-A minimum)
7. ✅ Test mode → live mode checklist completed
8. ✅ Monitoring/alerting on payment failures and webhook errors

Score: /8 — Below 5? Fix gaps before adding features.

Phase 1: Architecture Strategy

Integration Pattern Decision

Decision rule: Start with Checkout. Move to Payment Element only when you have specific UX requirements that Checkout can't solve.

Billing Model Selection

Project Structure

src/
  payments/
    stripe.config.ts        # Stripe client initialization
    webhooks.handler.ts     # Webhook endpoint + event routing
    checkout.service.ts     # Checkout session creation
    subscription.service.ts # Subscription lifecycle
    customer.service.ts     # Customer CRUD + portal
    invoice.service.ts      # Invoice customization
    tax.service.ts          # Tax calculation
    types.ts                # Shared types
  middleware/
    webhook-verify.ts       # Signature verification middleware

7 Architecture Rules

1. Never trust the client — verify payment status server-side via webhooks, never from redirect URLs
2. Webhooks are the source of truth — your database updates from webhook events, not API call responses
3. Idempotency everywhere — every mutating API call gets an idempotency key
4. One Stripe customer per user — create customer at signup, store stripe_customer_id in your DB
5. Metadata is your friend — attach user_id, plan, source to every object for debugging
6. Test mode mirrors live — your test environment should use the exact same code paths
7. Never store card numbers — use Stripe.js/Elements, never handle raw card data

Phase 2: Core Integration Patterns

Stripe Client Setup

// stripe.config.ts
import Stripe from 'stripe';

const stripe = new Stripe(process.env.STRIPE_SECRET_KEY!, {
  apiVersion: '2024-12-18.acacia',  // Pin API version!
  maxNetworkRetries: 2,
  timeout: 10_000,
  telemetry: false,
});

export { stripe };

Rules:

• Pin API version — never use rolling latest
• Set explicit timeout (10s default is fine)
• Disable telemetry in production if privacy-sensitive
• Use restricted keys with minimum required permissions

Customer Lifecycle

// customer.service.ts
async function getOrCreateCustomer(userId: string, email: string, name?: string) {
  // Check DB first
  const existing = await db.users.findOne({ id: userId });
  if (existing?.stripeCustomerId) {
    return existing.stripeCustomerId;
  }

  // Create in Stripe
  const customer = await stripe.customers.create({
    email,
    name,
    metadata: {
      user_id: userId,
      created_via: 'signup',
    },
  });

  // Store mapping
  await db.users.update({ id: userId }, { stripeCustomerId: customer.id });
  return customer.id;
}

Customer rules:

• Create at signup, not at first purchase
• Always set metadata.user_id for reverse lookups
• Store stripe_customer_id in your users table
• Use customer email updates to sync — listen for customer.updated

Checkout Session (Recommended Starting Point)

// checkout.service.ts
async function createCheckoutSession(params: {
  customerId: string;
  priceId: string;
  mode: 'payment' | 'subscription';
  successUrl: string;
  cancelUrl: string;
  metadata?: Record<string, string>;
}) {
  const session = await stripe.checkout.sessions.create({
    customer: params.customerId,
    mode: params.mode,
    line_items: [{ price: params.priceId, quantity: 1 }],
    success_url: `${params.successUrl}?session_id={CHECKOUT_SESSION_ID}`,
    cancel_url: params.cancelUrl,
    metadata: params.metadata ?? {},

    // Recommended defaults
    allow_promotion_codes: true,
    billing_address_collection: 'auto',
    tax_id_collection: { enabled: true },
    customer_update: { address: 'auto', name: 'auto' },
    payment_method_types: ['card'],
    
    // For subscriptions
    ...(params.mode === 'subscription' && {
      subscription_data: {
        metadata: params.metadata ?? {},
        trial_period_days: 14,
      },
    }),
  }, {
    idempotencyKey: `checkout_${params.customerId}_${params.priceId}_${Date.now()}`,
  });

  return session;
}

Payment Element (Custom UI)

// Server: create PaymentIntent
async function createPaymentIntent(params: {
  customerId: string;
  amount: number;      // in cents!
  currency: string;
  metadata?: Record<string, string>;
}) {
  return stripe.paymentIntents.create({
    customer: params.customerId,
    amount: params.amount,
    currency: params.currency,
    automatic_payment_methods: { enabled: true },
    metadata: {
      ...params.metadata,
      created_at: new Date().toISOString(),
    },
  }, {
    idempotencyKey: `pi_${params.customerId}_${params.amount}_${Date.now()}`,
  });
}

// Client: React Payment Element
// <PaymentElement /> handles all payment method rendering
// Use confirmPayment() on form submit

Phase 3: Subscription Management

Subscription Lifecycle Events

Created → Active → Past Due → Canceled → (optionally) Unpaid
                ↓
            Trialing → Active
                ↓
            Paused → Resumed → Active

Critical Webhook Events for Subscriptions

Plan Change Patterns

// Upgrade (immediate)
async function upgradePlan(subscriptionId: string, newPriceId: string) {
  const sub = await stripe.subscriptions.retrieve(subscriptionId);
  return stripe.subscriptions.update(subscriptionId, {
    items: [{
      id: sub.items.data[0].id,
      price: newPriceId,
    }],
    proration_behavior: 'create_prorations',  // charge difference immediately
    payment_behavior: 'error_if_incomplete',
  });
}

// Downgrade (at period end)
async function downgradePlan(subscriptionId: string, newPriceId: string) {
  const sub = await stripe.subscriptions.retrieve(subscriptionId);
  return stripe.subscriptions.update(subscriptionId, {
    items: [{
      id: sub.items.data[0].id,
      price: newPriceId,
    }],
    proration_behavior: 'none',               // no refund, change at renewal
    billing_cycle_anchor: 'unchanged',
  });
}

// Cancel (at period end — always prefer this)
async function cancelSubscription(subscriptionId: string) {
  return stripe.subscriptions.update(subscriptionId, {
    cancel_at_period_end: true,
  });
  // User keeps access until period ends
  // Handle `customer.subscription.deleted` to revoke
}

Dunning (Failed Payment Recovery)

# Stripe Dashboard → Settings → Subscriptions → Smart Retries
retry_schedule:
  attempt_1: 1 day after failure    # Smart timing
  attempt_2: 3 days after failure
  attempt_3: 5 days after failure
  attempt_4: 7 days after failure   # Final attempt

# Custom dunning emails (supplement Stripe's built-in)
dunning_sequence:
  - day: 0
    action: "Email: payment failed, update card link"
    template: "Your payment of {amount} failed. Update → {portal_url}"
  - day: 3
    action: "Email: second notice, urgency"
    template: "Still unable to charge. Update payment to avoid interruption."
  - day: 5
    action: "Email: final warning"
    template: "Last chance to update. Access pauses in 48 hours."
  - day: 7
    action: "Pause or cancel subscription"
    note: "Automatic via Stripe if all retries fail"

Usage-Based Billing

// Report usage for metered billing
async function reportUsage(subscriptionItemId: string, quantity: number) {
  return stripe.subscriptionItems.createUsageRecord(subscriptionItemId, {
    quantity,
    timestamp: Math.floor(Date.now() / 1000),
    action: 'increment',  // or 'set' for absolute value
  }, {
    idempotencyKey: `usage_${subscriptionItemId}_${Date.now()}`,
  });
}

// Best practice: batch usage reports
// Don't report every API call individually — aggregate per hour/day
// Report at least daily to avoid surprise bills at period end

Phase 4: Webhooks (The Most Critical Part)

Webhook Handler Template

// webhooks.handler.ts
import { stripe } from './stripe.config';
import type { Request, Response } from 'express';

const WEBHOOK_SECRET = process.env.STRIPE_WEBHOOK_SECRET!;

// Event handlers map
const handlers: Record<string, (event: Stripe.Event) => Promise<void>> = {
  'checkout.session.completed': handleCheckoutCompleted,
  'customer.subscription.created': handleSubscriptionCreated,
  'customer.subscription.updated': handleSubscriptionUpdated,
  'customer.subscription.deleted': handleSubscriptionDeleted,
  'invoice.payment_succeeded': handleInvoicePaymentSucceeded,
  'invoice.payment_failed': handleInvoicePaymentFailed,
  'customer.subscription.trial_will_end': handleTrialEnding,
  'payment_intent.succeeded': handlePaymentSucceeded,
  'payment_intent.payment_failed': handlePaymentFailed,
};

export async function handleWebhook(req: Request, res: Response) {
  // 1. Verify signature (NEVER skip this)
  let event: Stripe.Event;
  try {
    event = stripe.webhooks.constructEvent(
      req.body,        // raw body, not parsed JSON!
      req.headers['stripe-signature']!,
      WEBHOOK_SECRET,
    );
  } catch (err) {
    console.error('Webhook signature verification failed:', err);
    return res.status(400).send('Invalid signature');
  }

  // 2. Idempotency check
  const alreadyProcessed = await db.webhookEvents.findOne({ eventId: event.id });
  if (alreadyProcessed) {
    return res.status(200).json({ received: true, duplicate: true });
  }

  // 3. Route to handler
  const handler = handlers[event.type];
  if (handler) {
    try {
      await handler(event);
      await db.webhookEvents.insert({ eventId: event.id, type: event.type, processedAt: new Date() });
    } catch (err) {
      console.error(`Webhook handler failed for ${event.type}:`, err);
      return res.status(500).send('Handler error');  // Stripe will retry
    }
  }

  // 4. Always return 200 quickly
  res.status(200).json({ received: true });
}

10 Webhook Rules

1. Verify every signature — never process unverified events
2. Use raw body — don't parse JSON before verification (Express: express.raw({type: 'application/json'}))
3. Idempotency — store processed event IDs, handle duplicates gracefully
4. Return 200 fast — do heavy processing async/in background
5. Handle out-of-order — events may arrive in unexpected order; check current state before applying
6. Don't rely on event data alone — for critical actions, re-fetch the object from the API
7. Log everything — event ID, type, relevant object IDs, processing result
8. Monitor failures — alert on repeated 500s or unhandled event types
9. Use CLI for local dev — stripe listen --forward-to localhost:3000/webhooks
10. Register only events you handle — don't subscribe to everything

Essential Events by Use Case

Phase 5: Customer Portal & Self-Service

// Customer portal — saves you building billing UI
async function createPortalSession(customerId: string, returnUrl: string) {
  return stripe.billingPortal.sessions.create({
    customer: customerId,
    return_url: returnUrl,
  });
}

// Configure in Dashboard → Settings → Customer portal
// Enable: Update payment method, Cancel subscription, View invoices
// Optional: Plan switching, Invoice history download

Portal Configuration Checklist

• Payment method update enabled
• Subscription cancellation with reason collection
• Plan switching with proration preview
• Invoice history visible
• Business information (name, logo) set
• Return URL configured
• Terms of service / privacy policy linked

Phase 6: Tax Collection

Tax Decision Tree

Do you sell to EU customers?
  YES → Need VAT collection
    Use Stripe Tax (automatic) OR manual tax rates
  NO → 
Do you sell to US customers in multiple states?
  YES → Need sales tax (nexus rules)
    Use Stripe Tax (automatic) — manual is nightmare
  NO →
Do you exceed $100K revenue or 200 transactions in any US state?
  YES → You have economic nexus — collect tax
  NO → May not need to collect, but verify with accountant

Stripe Tax Setup

// Enable automatic tax on Checkout
const session = await stripe.checkout.sessions.create({
  // ... other config
  automatic_tax: { enabled: true },
  customer_update: { address: 'auto' },  // Required for tax calculation
});

// For subscriptions via API
const subscription = await stripe.subscriptions.create({
  customer: customerId,
  items: [{ price: priceId }],
  automatic_tax: { enabled: true },
});

Tax rules:

• Stripe Tax handles calculation + collection automatically
• You still need to file/remit taxes yourself (or use Stripe Tax filing in supported regions)
• Always collect billing address for accurate tax calculation
• Enable tax ID collection for B2B reverse charge (EU)

Phase 7: Stripe Connect (Marketplaces & Platforms)

Connect Account Types

Decision rule: Use Express unless you have a specific reason not to.

Payment Flow Patterns

// Direct charge (platform takes cut)
const paymentIntent = await stripe.paymentIntents.create({
  amount: 10000,  // $100
  currency: 'usd',
  application_fee_amount: 1500,  // $15 platform fee
  transfer_data: {
    destination: 'acct_seller123',
  },
});

// Destination charge (seller's Stripe processes)
// Same as above but payment appears on seller's statement

// Separate charges and transfers (most flexible)
const charge = await stripe.paymentIntents.create({
  amount: 10000,
  currency: 'usd',
});
// Then transfer to seller
const transfer = await stripe.transfers.create({
  amount: 8500,
  currency: 'usd',
  destination: 'acct_seller123',
  transfer_group: 'order_123',
});

Phase 8: Testing Strategy

Test Mode Checklist

Stripe CLI for Local Development

# Install
brew install stripe/stripe-cli/stripe

# Login
stripe login

# Forward webhooks to local server
stripe listen --forward-to localhost:3000/api/webhooks/stripe

# Trigger specific events for testing
stripe trigger checkout.session.completed
stripe trigger invoice.payment_failed
stripe trigger customer.subscription.deleted

Phase 9: Security & PCI Compliance

PCI Compliance Levels

Security Checklist (P0 — Mandatory)

• API keys in environment variables, never in code
• Webhook signatures verified on every request
• Restricted API keys with minimum permissions
• HTTPS everywhere (Stripe requires it)
• No card numbers logged, stored, or transmitted
• CSRF protection on payment endpoints
• Rate limiting on checkout creation
• Idempotency keys on all mutating calls

API Key Strategy

Live mode:
  sk_live_xxx    → Server only, env var, restricted permissions
  pk_live_xxx    → Client-side (public, safe to expose)
  whsec_xxx      → Webhook secret, server only

Test mode:
  sk_test_xxx    → Same restrictions as live
  pk_test_xxx    → Client-side
  whsec_test_xxx → Webhook secret (different from live!)

Restricted key permissions (create in Dashboard → API Keys):

• Checkout Sessions: Write
• Customers: Write
• Subscriptions: Read/Write
• Webhook Endpoints: Read
• Everything else: None

Phase 10: Go-Live Checklist

Pre-Launch (P0 — Mandatory)

• Webhook endpoint registered and verified in live mode
• All webhook events subscribed (same as test)
• Live API keys in production environment
• Customer portal configured with live branding
• Test a real $1 payment end-to-end (then refund)
• Error handling for all payment states (success, failure, pending, requires_action)
• Logging: payment ID, customer ID, amount, status on every transaction
• PCI SAQ-A completed in Stripe Dashboard

Pre-Launch (P1 — Within First Week)

• Monitoring: alert on payment failure rate > 5%
• Monitoring: alert on webhook delivery failures
• Receipt emails configured (Stripe auto-sends or custom)
• Refund process documented
• Dispute/chargeback response process
• Dunning emails active for subscriptions
• Stripe Tax enabled (if applicable)

Pre-Launch (P2 — Within First Month)

• Revenue analytics dashboard
• MRR/churn tracking
• Coupon/promotion code strategy
• Annual vs monthly pricing toggle
• Customer portal self-service verified

Phase 11: Monitoring & Operations

Key Metrics Dashboard

metrics:
  payment_success_rate:
    calculation: "successful_payments / total_attempts × 100"
    healthy: ">= 95%"
    warning: "90-95%"
    critical: "< 90%"
    
  webhook_delivery_rate:
    calculation: "successful_deliveries / total_events × 100"  
    healthy: ">= 99.5%"
    critical: "< 99%"
    
  average_revenue_per_user:
    calculation: "total_revenue / active_customers"
    track: "weekly trend"
    
  monthly_recurring_revenue:
    calculation: "sum(active_subscription_amounts)"
    track: "monthly growth rate"
    
  churn_rate:
    calculation: "canceled_subscriptions / total_active × 100"
    healthy: "< 5% monthly"
    warning: "5-10%"
    critical: "> 10%"
    
  involuntary_churn:
    calculation: "failed_payment_cancellations / total_churn × 100"
    note: "Should be < 30% of total churn — fix with better dunning"

Weekly Review Checklist

• Payment success rate vs last week
• Failed payments — any patterns? (card type, region, amount)
• Webhook failures — any endpoints timing out?
• New disputes/chargebacks — respond within 7 days
• Subscription metrics: new, churned, upgraded, downgraded
• Revenue: MRR, net new MRR, expansion MRR, contraction MRR

Phase 12: Advanced Patterns

Pricing Page with Annual Toggle

// Create both monthly and annual prices for each plan
const prices = {
  starter: {
    monthly: 'price_starter_monthly',   // $29/mo
    annual: 'price_starter_annual',     // $290/yr (save ~17%)
  },
  pro: {
    monthly: 'price_pro_monthly',       // $79/mo
    annual: 'price_pro_annual',         // $790/yr
  },
};

// Client toggles monthly/annual → creates checkout with correct priceId

Grandfathering & Price Increases

// New price, existing customers keep old price
// 1. Create new price object (don't modify existing)
// 2. New signups use new price
// 3. Existing subs stay on old price until they change plans
// 4. Optional: scheduled price migration with notice

async function schedulePriceIncrease(subscriptionId: string, newPriceId: string, effectiveDate: Date) {
  // Create a subscription schedule
  const schedule = await stripe.subscriptionSchedules.create({
    from_subscription: subscriptionId,
  });
  
  // Add phase with new price
  await stripe.subscriptionSchedules.update(schedule.id, {
    phases: [
      { items: [{ price: currentPriceId }], end_date: Math.floor(effectiveDate.getTime() / 1000) },
      { items: [{ price: newPriceId }] },
    ],
  });
}

Coupon & Promotion Codes

// Create coupon (reusable)
const coupon = await stripe.coupons.create({
  percent_off: 20,
  duration: 'repeating',
  duration_in_months: 3,
  max_redemptions: 100,
  metadata: { campaign: 'launch_2024' },
});

// Create promotion code (shareable link)
const promoCode = await stripe.promotionCodes.create({
  coupon: coupon.id,
  code: 'LAUNCH20',
  max_redemptions: 50,
  expires_at: Math.floor(new Date('2024-12-31').getTime() / 1000),
});

Handling Disputes (Chargebacks)

dispute_response_process:
  when_received:
    - Log dispute details: amount, reason, deadline
    - Alert team immediately
    - Begin evidence collection within 24 hours
    
  evidence_to_collect:
    - Customer communication (emails, chat logs)
    - Delivery proof (access logs, download records)
    - Terms of service acceptance timestamp
    - Refund policy shown at checkout
    - IP address and device fingerprint
    - Prior successful transactions from same customer
    
  submit:
    - Within 7 days (Stripe deadline is usually 21 days, but act fast)
    - Use Stripe Dashboard evidence submission form
    - Include written rebuttal addressing specific reason code
    
  prevention:
    - Clear billing descriptor (customer recognizes charge)
    - Send receipt emails immediately
    - Offer easy refunds before disputes escalate
    - Use Radar for fraud detection

10 Common Mistakes

Quality Rubric (0-100)

Commands

The agent responds to these natural language requests:

1. "Set up Stripe checkout" → Full Checkout integration with webhook handler
2. "Add subscriptions" → Subscription lifecycle with plan changes and dunning
3. "Configure webhooks" → Webhook handler with signature verification and idempotency
4. "Set up customer portal" → Billing portal configuration
5. "Add usage-based billing" → Metered subscription with usage reporting
6. "Stripe security audit" → PCI compliance check + security hardening
7. "Go-live checklist" → Pre-launch verification for production
8. "Set up Stripe Connect" → Marketplace/platform payment flows
9. "Add coupons and promos" → Promotion code system
10. "Review payment metrics" → Revenue and payment health dashboard
11. "Handle a dispute" → Chargeback response process
12. "Migrate pricing" → Grandfathering and price increase strategy