Sage 50 Canada

My sage 50 emails do not show up in the Sent Box in Outlook 365. Does anyone know how I can fix this?

Running Sage 50 Premium 2016.2 on Windows 10, when I select the "Microsoft Print to PDF On Ne01" printer and "Print & Record" a Sales Invoice (does the same for quotes also & probably any other record & print job), the print job gets canceled by Sage…