I don't have ProSeries 2019, but I used to teach with QuickBooks and Zoom Text in a classroom environment. One thing I noticed is that programs still using the old-style "Windows XP pop up print or save dialog" (sorry, that's the best way I can describe it) would hang up on occasion, as well as "print to file" functions. What we typically did then, instead of using "save as pdf" was to Print to a virtual PDF printer, which removed that function from the control of the Program. The program wouldn't know this was not a regular printer, in other words. Windows 10 now has that function, but I used to install "CutePDF" printer for this reason.