Yes, it is possible to jailbreak an Apple Watch.

In 2018, a hacker released an Apple Watch jailbreak, but it doesn’t offer much utility for average users. It’s more for developers interested in getting a peek under the hood. The jailbreak is compatible with watchOS 4.1 and Apple Watch Series 3. It consists of a few read/write permissions and features.

In 2017, hacker Max Bazaliy demonstrated a watchOS 3 jailbreak at a convention, but he didn’t release the files to the public. Now that Apple Watches have ditched that version of the operating system, it’s an obsolete technology.

In all cases, the jailbreaks do not include App Store functionality, so the customization options are quite limited and far removed from the experience users have with a jailbroken iPhone.