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Leaking dormer, unsure how to proceed

Hello all! 

We have two dormers, both of which are causing leaks inside the house. One of them leaks all the way down to the first floor.

the roof was replaced a 8 years ago and it seems they just caulked that area. 


Do do any of you have a better suggestion as to how to repair this? 




the red arrow shows where the water problem is. I suspect the leak happens here as the old caulking is in poor condition and it’s the area where there is a lot of paint damage.



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