Roof leak help

The first place I'd look is where the roof of the dormer meets the roof of the house in the area on the other side of where that arrow is indicating.

The dormer roof, where it ties into the roof of the rest of the house should be flashed in to prevent leaks,

You may have to pull some shingles off the main roof to expose the flashing to see if it is compromised. If the roofers used metal valley type flashing, it should be ok unless there's a nail hole/holes in it or not wide enough to fully seal that area.

If it is just shingles overlaid lapping each other, they may be getting brittle.

How old is the roof? The older the roof, the more time you will have to take to remove shingles since they are long stuck to each other on the tar strips and if an older roof, they may be pretty brittle and a PITA to remove. They make a special tool to remove asphalt shingles where you can slide it under the shingles to get to the nails to remove them without tearing up the shingle above it.

Look up "Shingle Removal Tool" and you'll see what I'm talking about. The one I like had a handle that is slightly offset from the tool with a long flat blade that allows you to get under the shingles and on the end it has a notched area to get to the nails. Once you hook the nails, you use a hammer to hit the end of the raised handle back towards you to pull the nail.

Your picture shows a raised shingle or flashing edge at the foreground corner of the dormer. You might start by fixing that. Since you are doing it trial and error, lightly mark and date the stained ceiling to help distinguish new from old damage.

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Is there supposed to be flashing where the green line is?….

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I've put on a couple dozen roofs over the years but never a roof with dormers.

I can see no real need for flashing in that situation since it is under the eave of the dormer and for rain to get to that area in enough volume to cause a leak, you will have a whole lot of other problems to deal with------like a massive flood.

There will be flashing along the upright wall of the dormer where it meets the roof of the main structure.

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I can see no real need for flashing in that situation since it is under the eave of the dormer and for rain to get to that area in enough volume to cause a leak, you will have a whole lot of other problems to deal with------like a massive flood.

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You don’t think a strong wind could drive the water that is being funneled from above into that corner?

Caulk your where your facia ends at the end of the valley at the soffit. (The green line) then your crown molding, onto a roofing supply for caulk if you live in BR ABC roofing on green well spring rd

What’s your location?

BR

I can come check it out for you. One of my guys is like a bloodhound of water intrusion. I won’t charge you anything. If he finds it, just throw him some cash. Love helping out TD when I can

I had an "only during storms" leak at chimney flashing fixed once. It was hard to tiptoe over attic rafters to check after every hard rain. So I put this color-change sticky paper all over the chimney/roof junction and checked it from a floored area with a flashlight. After a year I was convinced that it had a good repair, and only then I had my stained ceiling fixed.

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