Patching a hole made by a
nail, screw, or any other type of penetration in a steep sloped roof is
easy. This method will work for wood shingles, slate, asphalt composition
shingles, tile, etc. All you do is tuck a piece of sheet metal up under the
piece with the hole in it so that the top of the metal is upslope of the
hole about an inch. Secure it in place with urethane caulking. See the
picture below. The black line represent shingles, the blue dotted lines the
hole made, and the red line a piece of sheet metal.