A user-friendly jailbreak for the Apple Watch could soon be available thanks to efforts of developer @ethanpepro. The jailbreak is currently being developed for watchOS 5.1.2 and is not available for public download yet. The new jailbreak is in contrast to the previous one that was available last year, which was more targeted at developers than end users.
https://www.notebookcheck.net/An-Apple-Watch-jailbreak-for-end-users-is-not-too-far-away.417126.0.html