Yes, we have received lots of those calls. We do the same as you to correct. I found this in a Sage knowledgebase post:
Note: If printing to Paperless Office PDF was previously working on the workstation, but suddenly stopped, it is likely the problem occurred after Microsoft Windows Updates were installed. Some Sage 100 users on Windows 10 workstations (even those on the most currently supported versions) have reported that sometimes a Microsoft Windows Update will delete registry entries and programs. We have found that Sage 100 PDF Converter registry entries disappear or become affected, requiring reinstallation and verification that the registry entries are replaced by reinstallation.
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Visit at your own risk: ?https://www.howtogeek.com/243581/windows-10-may-delete-your-programs-without-asking/