Lightroom to Photoshop and back not working

[ZCUDD7]

Having an issue with photos sent to photoshop not coming back to lightroom once I've saved and closed them. I've found if I do quick edits in photoshop (<5 minutes) then I generally get the photo back to lightroom without any issues. If I spend more time on it or have more complicated edits then it won't ever re-appear in Lightroom. Worst of all is that I can see the tiff file is sitting in the TemporaryEdits folder created by lightroom but it won't send back. 

I've already tried reinstalling both programs and resetting their preferences but to no avail. Has anyone else had this issue?

Running a 16gb M1 Mac Mini with the latest photoshop and lightroom updates installed. 

[ZCUDD7]

Bumping as I'm still having this issue. Did another fresh install of both programs with a reset of preferences yet I have this issue right off the bat.