Pull the shingles surrounding the vent off the roof to expose the flashing. Start with the shingles that cover the top of the flashing and work down.
Pry the old roofing nails used to secure the top of each removed shingle out of the roof with a pry bar. Take care not to inadvertently damage the shingles above the removed shingles.
Pry the roofing nails out of the edges of the vent flashing with the pry bar and lift the flashing off the vent.
Apply a heavy coat of roofing cement to the bottom edges of the flashing's flange, then lower the flashing onto the vent.
Drive roofing nails through the flange and into the roof with a hammer to secure the flashing in place.
Cut the new shingles with a utility blade until the shingles conform to the shape of the vent.
Apply roofing cement to the back of the new shingles and press them onto the roof and around the vent. Begin by covering the bottom of the flashing and work upward. Slide the uppermost replacement shingle between the roof and the above shingle.