We use Stripe Checkout to start a subscription, then rely on webhooks to activate services. Items can be added later with or without proration depending on the plan.

Events we handle

• checkout.session.completed → store customer, link to account
• customer.subscription.created/updated → sync status, current_period_end
• invoice.paid → extend access if needed
• customer.subscription.deleted → schedule shutdown/cleanup

Adding more servers

• If an item exists for a product, bump quantity
• Otherwise create a new subscription_item (with metadata for mapping)
• We typically bill on the next invoice, then provision immediately

Trials & grace

• Trials via Checkout; we track trial_end and nudge with email
• Grace states when payment fails; periodic reminders; eventual stop