A brilliant trick would be to wipe Windows, install Ubuntu, and insist on the user learning to use Bash for everything.
Some would say that's a kindness!
I knew of someone who would go to a particular "big box" retail establishment where the general help wears blue polo shirts, and the computer help wears shirts and ties, and reboot their PC's to the Puppy Linux he carried on his USB drive.
At same said establishment, I may have perhaps powered down at least a dozen PC's in an attempt to get some attention. I'm not proud of such alleged behavior, but in theory, I was just looking for someone to say some variation of, "I'll be with you as soon as I can." (Several managers had perhaps walked by, also -- too important to stop and help a lowly customer...if that indeed happened.)