HOW TO FIX LEAKS IN FRONT OF DORMER

year ago we had leak in flashing near dormer and handy man supposedly fixed it and redid flashing in front of another dormer. Now both leak and when I checked I see about 8 nails in the shingles in front of each dormer. they had sealant on top of them but most is gone now. The questions should any nails be exposed there. Should the first shingle snot be cemented down when you restart the shingles below the dormer and windows? We have roofer coming today but want to know what to expect.
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Sometimes face nailing is unavoidable in a repair but it is less than optimum as you have discovered. You will probably need to remove those shingles and perhaps more running along side the dormers. and apply flashing correctly and then replace the shingles without face nailing any of them. In order to flash correctly a few courses of siding may need to be removed and replaced so the flashing can go under it. If the leaks have damaged the roof sheathing some of that may need replacement as well. Depending on the height, the roof pitch, type of siding, and the extent of damage it could run 2 men about 2 days labor to get things right.
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Is the flashing nailed down and then the shingle cemented over it?
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