Although Islam recommends us to ask questions and clarify what we are unsure of, I think sometimes, it is possible to go too far with the questions. It's no longer asking questions, but questioning the reasoning, logicalness of something - it is easy to go from trying to clarify our own understanding to trying to make Islam make sense based on our understanding.
Wait, does that make sense?
It's a bit like the difference between"Is it compulsary to pray five times a day?" and "why do we need to pray 5x? once should be enough".
That's not a great example but I think you'll get what I mean.
I think, this problem mostly arises when there is a lack of Islamic knowledge.