Lightroom CC Not Syncing

I can upload and edit raws into Lightroom, but they are not syncing; edited TIFFS imported from photoshop will sync, but not raws or TIF files (from saving and closing the window).

Maybe in a related note, photos used to immediately import back to LRCC from photoshop when I would save and close the file, and since I updated to a M1 mac, they are only sent back when I use the "share image" button on the top right, which takes significantly longer.