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, 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 at 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 inches. 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.
Best of luck repairing/replacing your leaks!
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