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We just had a new roof installed on our home. The old roof was well beyond its service life and had been patched by the previous owners. We were aware of the issues when we bought the house and began getting quotes soon after moving in. We wound up using a local contractor that was recommended by the neighbors.
They seemed to do a good job overall, but one spot at a valley/wall junction started leaking. They have made two attempts to fix the leak. I don't know if the second attempt has worked, but the work they did looks terrible. It appears to me that they are trying to "band-aid" the problem by using more and more caulk instead of fixing the underlying issues. They even put some caulk between the brick joints (over the mortar). I don't see this helping since the brick is porous.
Here are some photos. What do you think?

Road surface Wood Asphalt Grey Building material
Wood Asphalt Road surface Grey Building material
Automotive tire Wood Brick Road surface Building material
 

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Wow! They did a terrible job on that. Not only is more caulking not going to help, but it could make actually repairing the underlying issue here more difficult for somebody who actually knows what the hell they're doing. Generally, chimneys or rap and flashing and counter flashing on top. And there is at least one or two shingles missing from where they should be which is why you're having penetration problems. My advice as a professional is to go and find somebody who knows exactly how to fix it, and pay the extra Penny or two to go ahead and have them do so so that the leaking. And there won't be damaged from it.
 
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