Webhooks present significant challenges when scaled, as they function within an event-driven architecture where developers do not control the event producer, leading to complexities such as message ordering, retries, and duplicates. Phil Leggetter, from his experience at Hookdeck, identifies critical strategies for managing webhooks, including idempotency techniques such as fetch-before-process, insert-or-update with timestamp checks, and tracking processing state per event ID. These approaches help mitigate issues like duplicate events and out-of-order delivery. Additionally, managing webhook bursts via queue-first processing and monitoring back pressure is essential for maintaining system stability, while observability through centralized event logging is crucial for incident response. The emergence of event destinations and event gateways, which offer direct event infrastructure delivery, represents an evolving landscape that provides new solutions for handling webhooks at scale, as demonstrated by Hookdeck’s Event Gateway, which addresses common webhook challenges such as burst protection, provider chaos, incident recovery, and real-time visibility.