Bad Underhanded question (too broad?)
An example of an underhanded question which I found too broad was the now-deleted one called "Print an unexpected obscenity". The task was to write a program to print any insult, provided that the insult-printing is sufficiently obfuscated and undetectable.
Is this particular question too broad, and too much like code-trolling? It attracted a number of answers whose output was well-documented. For example, the output of this much-upvoted Bash/otherUnixShell solution is easy to predict, and it isn't very subtle. (I'm aware that I'm not really approaching this with a sense of humour here. I did find it funny though.)
You think you deserve an entry in the manual of manliness? Let's see:
No manual entry for you!
Clearly, this isn't very underhanded.
TL;DR: Is it too broad to ask for any insult? And how unexpected does it need to be to qualify?
Better Underhanded question
Write a program that makes 2 + 2 = 5 was a very fun question. I think it is objective enough. The task is to write a program which appears to calculate 2+2 (not too broad; asking someone to make a specific calculation is about as specific as it gets), but misuse some language feature to make it output 5. My answer is here.
Some of the underhanded questions are too broad and too much like code-trolling. To an extent, underhanded is the new code-trolling. I wouldn't kill all of it with fire though. Some of the questions are good and objective. But others are too broad and hence too much like code-trolling.