How do I fix a leaking skylight?
A skylight (and any hole in the roof) needs flashing, not caulk. The flashing should be overlapped so that shingles above are on top of the flashing, and as it goes down the side, each piece is on top of the piece below, so that any water runs down the roof rather than in your home. The flashing should go up the side and under any lip from the top of the skylight so that rain from above cannot get in behind the flashing. And then all nails should be covered in a roofing caulk and under a shingle/above flashing/other protective layer.