Walter has two computers running Windows 10, but every time it upgrades, it forces him to reinstall his printers, even though he uses Google Cloud Print. Leo says that Google Cloud Print is going away because most printers now print wirelessly via WiFi. But they do recommend installing CUPS drivers. It's odd though that Windows breaks the connection to a wired printer when updated. Print directly via WiFi. It'll not only be easier to print, but it should also be easier to update. Look for a CUPS driver for your printer. That may be the easiest solution.
The chatroom suggests connecting your printer to your router.