The jailbreaking process for the Apple Watch Series appears to be on the progress, it is clear from some of the Tweets shared by @ethanpepro. From Tweets shared by this developer the process of development of jailbreaking tools for whole Apple Watch Series 1, 2, 3 & 4 including the latest Watch OS 5.1.2 and older versions is in the work. This attempt makes the process cakewalk and add new method for that purpose so end users can take advantages of it.
These Tweets from @ethanpepro mention that the master plan is to eventually release a full Open-sourced jailbreak process with a streamlined installation process. Previously this process dodge the whole developer-only deals that was given off by most of the Apple Watch jailbreak attempts. Now it is interesting to see that what type of changes this jailbreaking would bring for end users and which changes it accommodates.
Though ethanpepro hasn’t provided the ETA for the jailbreaking release but it has shared some evidences which supports its work. The proofs shared includes screenshot and videos that explaining the jailbreaking process. With this ethanpepro plans to release a public and open-source jailbreak that specially focus on ease-of-use and more streamlined installing. This is an incredible attempt to introduce a less of a developer only jailbreak.
If you are thinking about the benefits of Apple Watch jailbreak, you can do several things. It enables you to do things such as installing add-ons or tweaks along with that you can potentially develop custom Apple Watch faces. But if you have already upgraded your Watch OS firmware version, then you cannot get the advantage of this jailbreak tool to do so even when it is released so you have to wait till developer release supported jailbreaking tool.