A recent bug in Claude Code's CLI, caused by a changelog format change, highlights the challenges of rapid AI-assisted development. As release velocities increase, existing systems struggle to keep up, leading to potential drift between components and insufficient oversight on changes. Automation tools are needed to manage this new pace effectively and prevent issues like "changelog drift."

The article explores some of history's most unusual software bugs, highlighting how these glitches have impacted technology and user experiences. It reflects on what these bizarre errors can teach us about software development and the importance of robust testing practices to prevent similar issues in the future.