Climb onto your house’s roof, using a ladder, on a warm and dry day so the roof’s surface is not slippery. Run water around your house’s dormer using a garden hose, looking for areas where the water stops and does not flow down the roof. Have an assistant watch from inside the house where leaks have come through before to confirm if any water starts to leak.
Lift up or remove any shingles around areas where you suspect the water is leaking, using a small pry bar. Inspect the surface under the shingles for signs of water damage, including mold growth.
Examine the dormer’s surface for any missing or damaged siding. Apply silicone caulk to any damaged areas and install small sections of siding to patch any holes.
Inspect the metal flashing between the dormer and the roof’s surface, looking for signs of damage that can let water leak in. Probe the caulk seal between the flashing, dormer and roof shingles with a putty knife to see if the existing caulk is damaged or not adhering correctly.
Nail down any shingles you removed before. Strip out any damaged or worn caulk with the putty knife. Apply a thick bead of silicone caulk to all of the seams between the shingles, flashing and the dormer.