Leaking roof - looking for advice,

Hi all. My roof was recently shingled, and it is now leaking. The water is visible on the ceiling below (i.e. ‘downstream’) from where the chimney is. So, I’m guessing that the leak may be at the chimney/roof joint. The roof is very steep and I’m not comfortable walking on it. I did take a couple drone photos, and I would greatly appreciate it if any of the knowledgeable folks here might give me some advice on what might be wrong (I know it’s a long shot, based only on these photos).

I wonder about the debris that seems to be collecting on the top end of the chimney and if might be causing water to backup. (My roofer unfortunately has not be too responsive to my pleas for help,… but I will continue to follow-up with him.)


I would caulk the base where the factory put it together. It has old caulk not new. I seal, under the shingles to the metal. When their old and 100 holes in the base I watershield them, under the base and on top. Looks like Atlas laminate. Could be a nail in a butt joint below the base.

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Many thanks rooferama !

Rooferama is right, also trim the shingles back from the base about 3/8" to allow for drainage. When you pull the shingles to seal it, you’ll see dirt where the leaks are coming from, and I’d guess the pile of debris on the backside is where you’ll find it…

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I agree with all of that and have fixed many leaks by simply cutting a small waterway. Also make sure the first two courses up from bottom of flashing are dog eared.

My rule was first shingle that passes the pipe is when the flashing goes on. Mud the underside of the flashing and seal under and over each course.

He resealed the top counter -flashing.
But forgot to re-seal where the flat base flashing meets the walls of the chimney.
It might have got done across the back and sides of it.
But didnt get done Across the bottom front.

Id do that and re-apply across the counter-flashing again
And apply where the shingles meet the chimney.

DarkThirty,

Cement under flashing and under and over each course”
YES

By the time most roofers learn and understand this, they are too old to do anything with it.