This document summarizes the challenges faced by the authors in migrating their Gerrit integration from version 2.1 to newer versions over 1.5 years. Some key obstacles included missing extension points, issues with redeploying plugins, and difficulties extending the web UI. While many contributions were made back to the Gerrit community, ongoing rebasing and testing was still required to keep up with new Gerrit releases. Finding the right balance between external contributions and internal modifications remained an ongoing challenge.