Yeah. I finally just gave up the Jailbreak on my old 5S and updated to the latest OS. Unpaired my watch from my jailbroken 6S+ and paired it to the 5S. I am now updating one of my three watches to the latest. Once it's done, I'll re-pair it back to my 6S+. Guess I'll have to do that with my other two watches as well.wOS is actually part of iOS. So you can't update wOS with the current iOS.