Shift key for punctuation is not working with Universal Control.

Hi photobriangray,

It sounds like you are having an issue with Universal Control. We know how important this is for you, and we will help get you to the right place to find a resolution.

The first thing to try is to restart both devices at the same time. These steps can often resolve this type of issue:

• Shut down or restart your Mac - Apple Support

• Restart your iPhone - Apple Support

If the restart does not resolve the issue, then please make sure both devices are running the latest OS versions:

• Update macOS on Mac - Apple Support

• Update your iPhone or iPad - Apple Support

All the best!

Good afternoon photobriangray,

If the issue still persists after updating to macOS 13.3.1, it might be helpful for you to speak directly with Apple about this issue.  

They'll be in the best position to investigate this further.  Click the link below, choose the phone number for your region (or the closest one to it) from the list, and call when it is convenient. 

Contact Apple for support and service - Apple Support

Take care.