Our house has a typical mast for the incoming electric wires, and it has two guy wires for support. The guy wires are anchored in the roof just with half-inch bolts sticking through the shingles and sheathing, fastened to wooden blocking underneath, attached between rafters.
One of the anchors causes a continuous leak in rainy weather, about a gallon a week this time of year. The other one leaks just a tiny bit most of the time, just enough so the sheathing and nearby frame is slightly wet, but if rain is very heavy and the wind just right, it leaks enough to send water into the house.
I need to fix these, and wondered -- is this an appropriate way to anchor guy wires in a shingled roof -- to just punch a bolt through? My first thought was no, this is a dumb-nuts lazy approach almost guaranteed to leak. But I did some research and noticed others on youtube etc. do the same thing. So maybe the fix is just to apply more tar or some type of sealant around the bolts to stop the leak. Or is there some sort of anchor with proper flashing that would be better to use? In an hour of searching, I couldn't find any such part for sale, except for flat roofs.