How to Build Idempotent Stripe Webhook Handlers for File Delivery
A software team building a document-generation SaaS product shared lessons from hardening their post-payment fulfillment pipeline, which spans databases, PDF renderers, cloud storage, and email providers. The core insight was to treat Stripe webhooks not as a trigger to execute tasks, but as events that advance a persisted state machine. Before redirecting users to Stripe Checkout, the team persists all order data — including document content and a deterministic hash — so fulfillment can proceed even if the customer closes their browser after paying. To prevent duplicate processing, they use the Stripe Checkout Session ID as a unique database key and enforce a single generation job per purchase type, resetting only explicitly retryable failure states. Granular job statuses such as 'pdf_generation_failed' and 'email_failed' are stored separately from purchase status, allowing engineers to diagnose and recover from failures at each stage independently.
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