@texasswede I would agree with you, but for some reason I have a 1.0 UE deployed on a custom record that generates a work order. The work order has a 2.0 UE deployed on it, and for some reason it is not firing

It's not because of UE1 and UE2.0. User events will never fire other user events, so even if the two of them were SS1.0, the second one still wouldn't fire.