Apple Watch series 5 screenshots not working

Hi not1lost,

Thanks for reaching out here in the Apple Support Communities. It looks like the screenshot feature is no longer working on your Apple Watch. We're glad to help.

You've done some good troubleshooting steps already.

Next, make sure that the screenshot feature is still enabled.

1. On your iPhone, open the Apple Watch app. 
2. Tap the My Watch tab, then tap General. 
3. Scroll down, then turn on Enable Screenshots.

This explains more:

How to take a screenshot on Apple Watch - Apple Support

Take Care.

Hi not1lost,

Since those steps didn't get this working again, and it has worked in the past, let's isolate a little more.

• Does the Digital Crown and the side button work properly for other tasks, such as using Siri or navigating to the Home screen?

This explains some of those features: How to use your Apple Watch - Apple Support

• If the other features work properly, try unpairing your Apple Watch, and pairing it again. This article has a section explaining how to do that: If your Apple Watch isn't connected or paired with your iPhone - Apple Support

All the Best.