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We had the brick chimney taken down and replaced with a wood framed/stucco chase, and had a new roof installed at the same time. Last year I was in the attic space during a rain, and noticed a drop of water forming inside where the new stucco meets the old stucco, right under the roof. I think the problem is that water flows down the roof, hits the flashing at the chimney, some water goes onto the roof, some goes over the edge of the roof and trickles along the top edge where the stucco meets the outrigger. There were 3 different contractors involved (the stucco guy, roofers, the guys that built chimney chase), none of them have been able to tell me how it should be fixed.

The outrigger is very close to the chimney chase sheathing, too close to properly get the stucco in there, leaving a gap, and a conduit for water. The stucco should be completely dry under the roof overhang, but it's usually the first area to show as wet.

I don't know exactly how this should have been built, but short of taking the shingles back, pulling the flashing, moving the outrigger and patching the stucco back... seems like a lot of work.

My thought is to make up a flashing to slide under the shingles that forces the water coming down the roof to stay on the roof, going around the roof side of the chimney chase. And maybe an extension of the counter flashing further away from the edge of the roof so water coming down the side of the chimney chase doesn't go immediately along the edge of the stucco where the outrigger is.

What should I do here?

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From your 2nd pic, I'd guess the water is getting in at the joint between flashing and stucco, lower right corner. Best fix would be to re-do the back pan flashing, giving it just a little pitch towards the roof side, setting it into some good (urethane based) caulking in that corner.
 
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