Originating from Israeli-Army slang. The original/canonical kitbag question explains its meaning quite well:
A soldier asks: "Do we need to bring our kitbags?" (A kitbag is heavy bag that soldiers have)
Commander: "Yes, of course, bring your kitbags!"
The commander would had not given the order had the kitbag question not been asked.. Because of asking the question, the soldier has caused grief for himself and the fellow soldiers from his squad.