If anyone is experiencing this issue like me, you can manually change the date on your phone to 12/31/23, then open your Wear app, manually update your watch, and then change the date back to automatic. Should fix it!

Another W for the Casio F-91W

The date change fix works if you only have one watch but it still won’t auto switch if you have two, at least it kept breaking for me. I ended up having to uninstall the wearable app, reset both of my watches, and then resync them to my phone for switching to work.