In the realm of distributed systems, the transactional outbox pattern provides a robust solution for ensuring reliable event delivery, particularly when dealing with webhooks. This approach integrates event publication within the same transaction as the business operation, thereby guaranteeing atomic operations, assured delivery, and exactly-once processing, even in the event of system failures. Implemented using Go and SQLite, the pattern involves two main components: an ingest service that creates business objects and associated events within a single transaction, and a worker service that processes pending events to dispatch them to a webhook gateway. The pattern's design ensures that if either the creation of business data or events fails, the entire transaction is rolled back, maintaining data consistency. With scalability in mind, the system leverages features such as database connection pooling, rate limiting, and message queues to handle high throughput, while operational guidelines focus on database performance, worker configuration, monitoring, and error handling. Overall, the transactional outbox pattern ensures a reliable webhook delivery system capable of maintaining data integrity and operational efficiency even under challenging conditions.