pipe collar on roof

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I was at my future retirement home in DE and looked at a sewer vent pipe from the attic side and could see daylight. I do not think that should happen.

So the choice is to slide a new collar over the existing collar (they did that in This Old House). Or remove old collar and its flashing base and some shingles and hope the shingles slide out OK, or some shingles will need to be replaced and of course I will never find matching ones.

I believe the existing roof is 10-15 years old. So about half its life.
 
There is a hard plastic "boot" that slips on over the vent pipe and lasts FOREVER. Available at Home Depot and Lowes. It is called a Perma-Boot. Measure to make sure it fits before buying. Most roof leaks happen at the vent stacks, and, can do a lot of damage if not caught right away.
 
I've always used the lead vent pipe seals. They slide over the pipe and are integrated in the shingles the normal way. The stack part is quite long. After getting the shingle part done you measure the stack (it'll be taller than the pipe), cut it off 3-4" above the pipe and the fold it over pushing it into the pipe. It's quite easy, the lead is very soft and nothing messes it up - lifetime cure.
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older shingles on the sunny side can be brittle earlier, but working in the warmer weather helps, or just replace a few at the "flashing" as needed
 
It looks like Oakley makes a collar you just slide over the old collar. The Perma-Boot looks interesting, reviews mentioned needing to lengthen the stack pipe in some cases. Roof is older than I thought, more like 18 years old. So it's got another 10 years left. Maybe!
 
They only last about 10 years or so. Slip one on if it will solve the problem, as long as there are no cracks in the larger part of the cap ( at the bottom) just doing the upper part should work.
 
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