Slide a new roof jack sized to fit your vent pipe over the pipe.
Replacing a roof jack.
Carefully pry up the shingles around the roof jack using a flat pry bar.
The first step to replacing a damaged roof jack is to measure the size of the existing roof jack to make sure you purchase the correct size.
Place your ladder securely against the roof eave and climb up on the roof.
Pry up the old jack and remove it by pulling it up over the vent pipe.
Installing new shingles is a major investment for most homeowners so it makes good sense to take steps to protect the integrity.
On the boots if you have metal roof jacks with rubber boot seals on top with many models the rubber seals can be popped off and replaced without removing the metal part and there are also slip over boots that can just nestle down over the existing damaged boot and overlap the top of the jack but contractor would have to look at it and see then go get parts so if using a contractor probably cheaper to just have him bring new ones right off unless quite close to his supply wholesaler.
Is it necessary to replace roof flashings when replacing shingles.