'Now Playing' on my watch now 'not playing'

I had this issue too and it lead me to checking my Bluetooth settings on my watch. It kept showing that my iPhone wasn't connected. I tried to connect it back, but it kept saying that it was incompatible. That then lead me to this article https://support.apple.com/en-us/HT20502. I noticed that I was seeing the red phone icon in my connection center and couldn't get it to turn green. I had to 'Erase all content and settings' on the watch then re-pair it with my iPhone. Now Playing started to work after that.

It sounds like you did a good job of troubleshooting. You are not alone. See:

Now Playing on my Apple Watch no longer w… - Apple Community

All I can further suggest is to use the 'Get Support' link at the top-right corner of this page.

Okay I’m having the same issues with Now Playing not working with any of my music apps. I have restarted both my devices, I have unpaired and re-paired my phone and watch. It’s still not working. It was working prior to the latest update 😡

I am having the same problem. Watch does not show Now Playing, just Not Playing. Tried all the trouble shooting too.

If anyone still having this problem this did it for me. I just keep opening “now playing” manually on the watch and eventually it started working like before