Slack experienced a significant outage on May 12, 2020, due to a technical issue with their HAProxy server state management. The problem was caused by a bug in the program that synced the host list with the HAProxy server state, which led to a stale list of backends and ultimately resulted in the outage. The issue was resolved with a rolling restart of the HAProxy fleet. The incident highlighted the importance of monitoring and testing, particularly for systems that have been working reliably for a long time.