> after enough instances of "I'm trying to do X. It's not working. Help." type messages.

Related to this, I will never for the life of me understand why people think it's okay to say "I get an error" without saying what the error is.

I don't expect a non-technical person to understand the error, but I do expect a non-technical person to know that what the error message is is useful to the person trying to help you and to proactively provide the contents of the error message, even if it's a shitty cell phone picture of the error.