I'm crap at summarizing. Basically it's a question that the person asking usually should know the answer to, or one that is ambiguous enough to give the person asking the benefit of the doubt if left unanswered. **Example** --- **Person A**: *Please organize this chart alphabetically* **Person B**: *Should I also color code the important entries?* **Person A**: *Yes, of course.* In this scenario, Person B asked a Kitbag question. If he hadn't asked it, he would have done his job, Person A would be happy and everything would be ok. But now, Person A expects Person B to do two things, which he now has to do. Person B made his own job harder because he asked a Kitbag question. **Etymology** --- The word/expression comes from IDF slang. Where a kitbag usually refers to a bag of the soldier's personal belongings. The expression originated from a situation in the army when soldiers were ordered to move from point A to point B, and the soldiers asked their commanders if they should carry their kibag with them, to which the answer was of course, yes they should.