Painful would be the several (!) times I had to check the computer over after they fell for a tech help scam and lost money. The stupid thing was that if someone tried to sell them something on the street or phone they were smart enough to refuse, but for some reason a popup on the computer makes things legit. Even after it was a scam the last time it happened. Why?

There are many more lesser events that aren’t painful as much as just tedious, but I think having some patience and knowing what to tell them (vs. actually explaining it) helped. I tried to reduce the complexity and lock things down, but in the end it was just easier to come over and fix the problem every now and then.