I am using the latest version 11.0 for Lightroom CC, Camera RAW 14 and Photoshop 23.01 on an iMac.
Whilst in Lightroom, when I choose 'Edit, Edit in Photoshop', I regularly find the progress bar either sticks when it gets to the end and nothing happens, or, it remains greyed out and the image doesn't transfer. Even canceling the process doesn't remove the Progress bar. Sometimes the only way I can get rid of it is by closing Photoshop down completely, which is a pain! Now and again it does the transfer to Photoshop but the progress bar remains hovering like a guest overstaying their welcome!
Thank you for your reply but I'm not sure what you mean, referring to 'Resetting my Preferences for LR and PS'. I'm not aware that specific settings need to be set up for the 'Edit in Photoshop' feature in Lightroom CC. And I haven't altered the preferences when updating the latest versions of LR and PS. I didn't have this problem with previous versions.
When the "link" between LR and Photoshop gets wonky, it is worth trying the following: Use the CC application to uninstall both products but DO keep your prefernces when asked. Now install Photoshop FIRST, then Lightroom Classic. Any better?
Author “Color Management for Photographers" & "Photoshop CC Color Management"