Our company recently encountered a massive issue with 404 errors due to changes in our documentation structure, which led to all existing links collapsing and resulting in a flood of Not Found Responses. To address this problem, we utilized Sentry's insights tool Discover to identify the scope of the issue and prioritize content based on user or request count. We then used Metric Alerts to notify developers if any future deployment caused an increase in 404s. Additionally, we developed a homegrown linkchecker to evaluate and identify broken links and anchors, requiring all links to pass this test prior to merging. By taking these steps, we were able to effectively manage the issue and create documentation that helps users navigate our platform efficiently.