Anyone else getting an error when printing tax returns to DMS but only for certain clients?

We only have this issue for a couple clients.  and its the same clients for the last 2 years. 

Right now we are printing to PDF saving it on our desktop and then drag & drop it into the client DMS file.  

I have tried doing the Lacerte Tool Hub repairs, the F10 PDF repair in Lacerte, and sending the clients profile from Lacerte to DMS again. 

Any ideas on what else I should do?