Tailscale experienced a series of database corruption incidents caused by a 16-year-old bug in SQLite, which they were able to identify and fix with the help of the SQLite developers. The bug, known as the WAL-Reset bug, occurred due to a rare data race condition in the checkpointing process. Tailscale's use of manual checkpointing and aggressive checkpointing made them more likely to encounter the bug. The company was able to resolve the issue by purchasing a professional support contract with the SQLite developers and working together to create a debugging tool.