Before installing the threshold on the floor, lay down a generous bead of silicon caulk.
After completing the cuts, pry away the sheathing, then apply a generous bead of caulking on either side of the gap.
To attach the jambs to the walls, apply a generous bead of silicone caulking compound (often supplied, but also available at hardware stores) in a continuous strip along the rear surface of each jamb.
Cover the nailheads with roofing cement and apply a generous bead of cement under the shingles, then press the shingles in place.
Also, apply a generous bead of caulking compound to the surface as weatherstripping.
Apply a generous bead of new roofing cement to the back of the patch, then position it so it covers the damaged area.
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Also apply a generous bead of caulking, as weatherstripping, to surfaces the sill will rest on.
Lift the overlapping shingles around the cap, apply a generous bead of roofing cement beneath them and press in place.