Hi all , i am looking forward to hearing from all the roof experts that view this forum. I was going through some old home improvement construction pictures the other day and came across some pictures i took off one of my "mysterious" nail problems i had with my roof. As i recall it was a total of three in a relatively short period. It was probably over a two month period during the spring of 2013. It was two roofing nails and one roofing board nail. My house was built in the 50's and has 1 bye's running under the shingles. I discovered the roofing nail holes thanks to the rain leaving a water spot on the ceiling in the kitchen. The other was a drip in the basement, It was lined up with a wall and ran all the way down to the basement where it left a puddle on the floor. The third and last was the most puzzling. I discovered this one while i was on a ladder cleaning out the gutters. See the following pictures.
Has anyone seen this happen before ? or have any idea how the one in the picture occurs?