This has stopped working for me. I’ve tested it with PocketCasts, Castro and Podcasts as well as Spotify. If I click Now Playing on the watch it brings up the interface but it’s blank and says not playing. Anyone else experiencing this?
I know it’s not much help but I’m on a series 5 and this stopped working with watchOS 9 for me. I think it’s a bug or oversight by Apple but I can’t figure out how to fix it. 
Thanks for replying. It’s definitely been working for me on OS9 until last week. Let’s hope they can sort it.
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I often find the behaviour of Now Playing quite confusing. If it’s showing what’s playing directly from your watch for example, but the audio is actually playing on your iPhone, Now Playing will say nothing’s playing.
If you tap the back arrow at the top left, you’ll get a list of all your devices that can play audio. If you select the device that’s actually playing the audio in there (presumably your iPhone), does it show what’s playing?
Ok, so I think I fixed it on my device (so far). What I did?
- Deleted Now Playing and re-installed it. (Long press on App List and select Edit and then delete the app. Open the App Store on the watch and re-download Now Playing.)
- Force shutdown and restarted the watch. (Press and hold both buttons until the watch restarts.)
A combination of these two steps seems to have kicked it into gear. We’ll see if that continues.
Latest watchOS update fixed this.