This occurs through a talmid’s inquisitiveness where the Rav Haflaah in Parahas Bo says that a kashye comes from a siyata Dishmaya, Divine intervention by helping the rebbi to reveal the sodos Hatorah, the hidden part of the Torah. He compares this to a simpleton who receives a diamond. Liking gold, he goes to a goldsmith to get it covered with gold. The goldsmith is no expert, so he leaves some holes. The simple person sees only the gold but the smart person sees the diamond underneath the gold. This can be the comparison to the bitter water becoming sweet through a bitter tree. One learns a piece of gemara and its bitter because he does not understand it at all even to ask a kashye, Now he gets a siyata dishmaya to ask a kashye which is still bitter without an answer. When he finds an answer, it becomes sweet. The talmidim help the rebbi by asking kashyes to find answers.
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