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Fixing roof leak at chimney

Sukhoi

Elite Member
Started to get a spot in the ceiling in front of the chimney, so I went up into the attic to look. There are a few slowly dripping leaks along with width of the chimney.
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On the roof the shingles look ok above the chimney, and the flashing at roof level does not have obvious problems. The "caulking" at the top of the flashing is highly fractured and falling out. Is this likely the failure site? This is also the side facing the wind/rain. I have a tube of Black Jack Rubr-Seal roof & flashing cement. Should I remove the broken "caulking" and fill that area with this? I don't want to screw up a permanent repair if for whatever reason this would not be considered permanent.
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The roof pic is from yesterday which is why it's dry.
 
Damn, that looks like caulking on the second row of bricks in your chimney, outside pic. Sheesh. Didn't know there was caulk you could use in place of mortar with brick.

And looks kinda like you've got new roof shingles in your future, too.
 
Yeah it's this weird sort of layered stuff. I decided to try to apply the rubberized cement today, and could barely get it to stick to the wet flashing. The caulking area was actually pretty dry (while it was actively dripping inside), the flashing didn't have any obvious holes on the uphill side, and from that I'm leaning toward the problem being a fundamental one between the shingles and flashing on the sides. Something just doesn't seem right with the way things are laying.

We just got gutters put on a month ago (there never were any, go figure), so I sent an e-mail to the same roofing company to see about fixing this. The flashing is the same sheet metal as the kitchen exhaust, which I know is original to the house from 1965 so I suspect the chimney flashing is too. The one new roof put on about 20 yr ago was put on top of the old one.

I agree the shingles don't look the best, but the roofing company for the gutters said they thought we had around 8 years left. I'm figuring to do it in about 5 years. The ridge cap was all replaced recently and is in better shape than the rest.
 
If a new roof is in your future you may want to consider having a saddle constructed to divert water away from that portion of your chimney. They are sometimes called a cricket. Different terminology, same thing. The construction of it is more than likely beyond the scope of work that a roofing company would typically do but perhaps not.

Just Google chimney saddle and you'll see what I'm talking about.
 
Yeah good call. I saw those when I was researching this problem. Apparently they're only mandatory with 36"+ chimneys, and mine is about 28". But I agree it would be a good idea. I think I could get away with a small one just made from flashing, which a roofing company should be able to handle.
 
On the right bottom of the chimney (as it's pictured) which looks to be the actual top right of the chimney seems like there's a shingle missing. Can't tell if that's caulked or flashed but looks like water could get under there.

Mine is also leaking and due to the weather best band aid I could find was flex-seal. It's working so far.
 
Hmm, are you speaking of the change in shingle color with the distinct line? It could be, but I expect I would have noticed that when I was up there. I hope to have a roofer coming in the next couple days to deal with the situation. If not, I'll head on there on Thursday when it's dry, inspect, and slather some better sealant on in areas that make sense.

Oh nevermind, I think you mean where more flashing is visible. Yes I'm not sure what is going on there. The other side is the same, except the other side has that gap all the way down. No clue how wide the flashing is underneath.
 
Hmm, are you speaking of the change in shingle color with the distinct line? It could be, but I expect I would have noticed that when I was up there. I hope to have a roofer coming in the next couple days to deal with the situation. If not, I'll head on there on Thursday when it's dry, inspect, and slather some better sealant on in areas that make sense.

Oh nevermind, I think you mean where more flashing is visible. Yes I'm not sure what is going on there. The other side is the same, except the other side has that gap all the way down. No clue how wide the flashing is underneath.

Scratch my Flex Seal idea. My chimney is leaking again lol.
 
I had one of Greenman's guys out on Saturday who was a roofer for 25 years. He redid the caulk above the counter flashing and thinks that was the problem. The main flashing looks good enough despite the age. He said if this doesn't fix it he thinks the water is being absorbed by the bricks and mortar, and I would need to fix with a spray sealer once things dry out this summer.
 
Do something about the termites as well.

Use two layers of flashing per side, a continuous piece first and over it shorter segments layered like the shingles. The latter lets water run off. Using just a continuous piece of flashing will make water run down under several rows of shingles.
 
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