It’s becoming common practice to use a self adhesive membrane (peel & stick) around a curbed skylight installation, with the membrane affixed to either the felt or to the plywood roof decking. What happens when there are three layers of roofing material to contend with? Does the self adhesive membrane ever get affixed to the second from the top layer or does it go down on the plywood and then the three layers of shingles get reinstalled up to the edge of the skylight?
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So, you are retrofitting a skylight to a roof w/3layers shingles
Wow, a balsy move to cut a hole in that mess.
I would seal the curb to the plywood, felt over the top (not up the sides). Shingle/step flash and overflash with the curb's metal.
that for new construction.
I don't think I'd guarantee, nor advise putting a skylight into a roof that already had 3 layers. Or, I'd advise stripping two b/4 applying another-anytime-skylight or not.