Problem:
The auto-name feature sometimes stops working and the Win2PDF File Save window appears.

Solution:
The auto-name feature can be cancelled by holding down the shift key. It's likely that the user was typing on the keyboard when Win2PDF was running in the background, and accidentally disabled the auto-name feature. You can disable the keyboard check by running the Win2PDF Admin Utility and checking the "Disable Auto-name Shift Key Check" option:

https://www.win2pdf.com/doc/enable-win2pdf-troubleshooting.html