I have had almost exactly the identical scenario myself, about the same feature, with the same kind of person.
After one such incident, I'm afraid I put you on the "extended diagnosis" tier, which means we talk to you over the phone like an idiot first, before we come and see you in person and realise you have not been doing something quite basic and obvious all along.
Like in my personal life, I assume nobody is an idiot or a genius, and pitch my assistance at that level. Then as I discover more about you, I may categorise you in either of those categories. Then technical conversations become much easier: "Have you plugged it in?" or "Yeah, you just need to resync the account" or whatever is appropriate to that level.
The fact that I have "downgraded" my support for you should tell you a lot about how skilled you actually are, and whether you should really be handling the kinds of data / responsibilities / systems that you are.