This is how I attach my pump jack pole brackets onto the roof. On a new roof, it’s quite easy to get under the shingles. With an older roof, I used an old pointed concrete trowel to get under the shingles. Once the project is complete, I seal up the holes and it’s good to go. I’ve never had a leak and I’ve even had a roofing company inspector show their gratitude while inspecting the new roof when they’ve seen me attach the brackets under the shingle. I’ve never had a known roof leak due to the