Our latest edition of Dogfooding Chronicles explores how Sentry updated its documentation to address a flood of 404 errors. The transition to a new structure led to a sea of broken links, causing embarrassment for the company and particularly ironic given their error monitoring focus. To solve this problem, Sentry used Discover to identify and prioritize content issues, Metric Alerts to monitor future deployments, and built a homegrown linkchecker to evaluate broken links and anchors. This effort demonstrates the importance of documentation in guiding reliable and performant code, even for developers who may not enjoy reading it.