He casually mentioned that he keeps getting logged out.

this is actually a very difficult issue imo: it's hard to know what you should expect from "tech stuff", even more so now that stuff is more advanced and the black boxes get more complicated. was it supposed to act like that? who knows. i can't really do anything about it, so i'll just cope with it. you just end up with problems that you "cope with" and never get solved if not for almost random happenstances like casually mentioning it to a more knowledgeable person or reading about it somewhere else and going, "huh, it wasn't supposed to do that after all." it's also made harder that the problems are more intractable? it isn't very intuitive that an unupdated browser could leave you in danger of hacks and stuff; the browser works for browsing, after all. updating windows is an even harder sell: you want me to make windows bother me even more with stuff i don't want and maybe changing stuff that already work fine?

even though i'd like to think i'm pretty savvy, i appreciate that i'm highly stupid, and thus i'm susceptible to this too. stuff's tough

(a fun "savvy but stupid" story: a long time ago i destroyed my windows 98 installation because my 4gb harddisk was full and i tried to make space by deleting stuff from C:/Windows and, wait for it, System32. this was without prompting; i didn't have internet at the time, so i didn't get Epic Memed; rather, i Epic Memed myself)