I've got a Moto360 and an old Nexus 4 with lollipop! I used trusted device and it worked well, but lately it is spotty at best. Same with trusted places but that is beside the point.

I'm rooted running a custom kernel but otherwise stock. Any ideas? Try to rest watch?

Edit: yeah I messed up the title... it is supposed to be working... These swypey keyboards hehe.