Fix Plumbing Vent Boots
Plumbing vent boots can be all plastic, plastic and metal, or even two-piece metal units. Check plastic bases for cracks and metal bases for broken seams. Then examine the rubber boot surrounding the pipe. That can be rotted away or torn, allowing water to work its way into the house along the pipe. With any of these problems, you should buy a new vent boot to replace the old one. But if the nails at the base are missing or pulled free and the boot is in good shape, replace them with the rubber-washered screws used for metal roofing systems. You'll find them at any home center with the rest of the screws. You'll have to work neighboring shingles free on both sides. If you don't have extra shingles, be careful when you remove shingles so they can be reused. Use a flat bar to separate the sealant between the layers. Then you'll be able to drive the flat bar under the nail heads to pop out the nails.
Fix Roof Vents
Fix Walls and Dormers
Water doesn't always come in at the shingled surface. Often, wind-driven rain comes in from above the roof, especially around windows, between corner boards and siding, and through cracks and knotholes in siding. Dormer walls provide lots of spots where water can dribble down and enter the roof. Caulk can be old, cracked or even missing between the corner boards and between window edges and siding. Water penetrates these cracks and works its way behind the flashing and into the house. Even caulk that looks intact may not be sealing against the adjoining surfaces. Dig around with a putty knife to see if the area is sealed. Dig out any suspect caulk and replace it with a siliconized latex caulk. Also check the siding above the step flashing. Replace any cracked, rotted or missing siding, making sure the new piece overlaps the step flashing by at least 2 in. If you still have a leak, pull the corner boards free and check the overlapping flashing at the corner. Often, there's old, hardened caulk where the two pieces overlap at the inside corner.