AlphaFrog would you happen to know why the code gets stuck when the path to the file is too long. I'm guessing that's the reason.
When I step through the code it gets stuck in this line:
With .Documents.Open("D:\Users\DMol\Desktop\Jimmy\BUSINESS AMERICA\Clients" & "\" & Cells(2, 2) & "\" & Cells(2, 2) & "_Business America 2017_Proposal.docx")
and then it shows this message:

2017-01-16_12-02-32.png