"The file can't be found" on Indesign Photoshop Illustrator files error

Having an ongoing issue opening Adobe files, Indesign .indd, Photoshop.psd / .tiff / Illustrator .ai .eps etc. 

When a file is more than a few weeks old and I try to reopen I get a 'The file can't be found" error. 

The icon for the file in Finder also doesn't display correctly / is missing (see screenshot)

There is nothing wrong with these files, not corrupt etc. 

I've found a workaround of copying and pasting the file into the finder window, this then "fixes" the original file and makes it openable.

It's a bit annoying to have to do this everytime especially with a large file though, and today that fix didn't work. 

Any advice? It's very annoying.