"When it rains, it pours", literally. Message from 6 year tenant, clothes on floor beside her bed soaked from last night's heavy rain. Had asphalt shingle roof replace in December of 2020, so less than 5 years old. This is the second house that guy has done that has leaked. He didn't answer the phone when I called at 8. No more by him, cheaper is not always better.

(ie, depending on how many roofs you own, it may be ordinary maintenance rather than a failure repair. Or it may be that he's less diligent about a certain type of thing-- ie, I have some roofers who are normally good but once neglected to place a boot around a vent pipe, so that meant there was a gappy hole until I got my handyman to fix that.)

That stinks. We had strong rain & thunderstorms overnight here, too.

I doubt the nuts would, but a branch falling end first certainly could.

Also check for any exposed nails that are not covered with tar, or a boot that was installed/looks new but was trimmed wrong to leave a gap around the pipe - or just installed wrong like just sat on top of the shingles.

Even when you hire someone, it seems you have to sit there & watch what they do all day long. I've caught a roofer making basic mistakes before : (.

Is this a stick-built house or mobile home? Sometimes folks put a different / heavier roof on a MH without building proper support for it. That can cause low spots & shingle breakage.

It's a stick built house, we put gutters on it too. This is the house the lady complained about mold all the time.

Check to make sure he's installing the pipe boots (the galvanized tin or plastic surround that goes around your roof vents, etc) correctly. If they're done right, on the roof slope below the pipe boot, you should be able to see the galvanized base panel of the pipe boot. The base of the pipe boot should be under the shingles on the slope above the boot, but on top of the shingles on the slope below the boot.

Google "How to Install a Plumbing Jack/Pipe Boot On Your Roof | Mr Happy House" and go the youtube video with the same name. Go to 1:58 in the youtube video and you'll see what it should look like.

One 5 unit apartment building with a garage I had redone by a discount roofer for $7,700 back in 1995. That same building I had redone in January 2025 for $29,000. You hire the right installer with the right products, it will last.

Another few properties I purchased back in 2007 with new roofs, didn't last. Only 18 years instead of 25-30. Those cost me $10,000, $29,000 and $38,000. If done right I would have gotten 10 more years..

I once read that the 3 most common reasons for roof leaks account for over 90% of leaks. From memory they are:

1) Penetrations: Plumbing, vents, skylights, etc. Usually the boot was incorrectly installed.

2) Valleys: When two plain's of a roof meet you can either install metal or overlap the shingles in a special pattern. If it's not done right, water seeps up under the side causing leaks.