Watch is running 5.0.1. When I run Watchmaker Legacy and push a new watch face it's applied properly, both the bright and dimmed faces and properly synced. If I switch my active watch face over to Watchmaker for AW5 only the dimmed watch face gets synced properly. When I wake the watch up, instead of seeing the bright version of my applied watch face I see the background of whichever card is first in my notifications list. It's almost like the bright version of the face just isn't there.

There's only one watch face in my library which gets applied properly on the AW5 version and I can't figure out what makes this one so special. If no one has a fix then the next thing I'll try is uninstalling and reinstalling the app.

Update: Uninstalling and reinstalling the app on my phone worked. Leaving this here in case anyone else runs into the same problem.