During the development of Windows 95, a placeholder dialog was added with the title, "In order to demonstrate our superior intellect, we will now ask you a question you cannot answer." The dialog itself asked a technical question that you need a brain the size of a planet in order to answer. (Okay, your brain didn't need to be quite that big.)
Of course, there was no intention of shipping Windows 95 with such a dialog. The dialog was there only until other infrastructure became available, permitting the system to answer the question automatically.
But when I saw that dialog, I was enlightened. As programmers, we often find ourselves unsure what to do next, and we say, "Well, to play it safe, I'll just ask the user what they want to do. I'm sure they'll make the right decision."
Except that they don't. The default answer to every dialog box is Cancel. If you ask the user a technical question, odds are they they're just going to stare at it blankly for a while, then try to cancel out of it. The lesson they've learned is "Computers are hard to use."
So don't ask questions the user can't answer. It doesn't get you anywhere and it just frustrates the user.