Damon gets a popup message "PDF Printer not initialized" when he tries to create a PDF in Windows. Leo says that a PDF printer will simulate a printer to create a digital document, and it sounds like Windows may have broken it in a recent update. Type Windows+KS to go into Windows features (or Windows key, type Windows Features). Turn it off. Then on. Then look for a check box for printing to PDF. Turn it off. Then go back in and turn it back on. That will reenable the Windows Print to PDF drivers. Here's an article that outlines it step by step.
Damon can also make the Windows Print to PDF the default printer in print settings. Lastly, he can remove the print to PDF driver, reboot, and then reinstall it. It's also possible that a third-party reader like Adobe Reader may have replaced it and that will cause a conflict.