Replace all rubber boots and replace metal penetration flashing.
Replace rubber boot on metal roof.
You will need only a few materials and they will all be available at your local home improvement store.
Plumbing vent pipes that extend through the roof come with metal flashing or rubber boot type flashing to seal the penetrations.
Figuring that the rubber collar on the new flashing may split before it s time to strip and replace the roof shingles another 20 years hopefully i first seal the vent pipe to the metal of existing flashing with protectowrap s form flash 2 flashing tape.
And begging to caulk around where the boot will go on the roof.
The best way for a do it yourselfer to repair a roof boot is to seal the existing boot and apply a new rain and repair pipe collar.
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.
Make sure you need a new boot may just need a bit of bitumastic caulk if it is leaking a bit at the duct contact as they commonly do as the rubber gets older.
I put in enough material that it squished out around the entire outside perimeter.
Now slide the boot down and make sure there is enough caulk to have a seamless circle all the way around.
The slide the boot down the pipe and leave it about 3 above the roof.
If split then yes it needs replacing though a good wrap with waterproof duct tape or bitumastic caulk will keep it intact and dry until a roofer can fix it.
Place the new boot in the hole of the pipe and cut the boot on the line that touches the rim.
Apply a liberal amount of silicone sealer to the old rubber boot.