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I was up on my roof investigating how bats are getting in, when I observed the following:

Dormer flashing

There are no leaks... yet. Due to presence of yellowjackets, I didn't take a long look, but it appears that when the roof was replaced 17 years ago, they put the shingles under this flashing. I couldn't see if they added new flashing under the new shingles. Then they loaded it down with caulk, and nailed it.

The caulk is failing, and many of the nails have popped up.

Is this something I should be concerned about? How do I address something like this?


Bonus question -- what would cause this, and should I be worried about it?

enter image description here

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    Search "step flashing" for a good idea what that area should look like.
    – isherwood
    Sep 1, 2020 at 18:59

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Should my dormer flashing look like this?

NO, at the very least it is an indicator of shoddy craftsmanship. At worst, it may indicate that no angled flashing was installed below the shingles and roof paper.

Is this something I should be concerned about?

You said there have been no leaks; so while you should have some concern, it should be tempered by the fact that it is not leaking (...yet)

How do I address something like this?

The proper way (if you are comfortable with roofing repair) would be to carefully remove the ugly flashing and each section of tab shingle adjacent to it, from the bottom of that lame old flashing all the way to the top under the dormer eave. Then properly install angled flashing or Z/angled flashing combination along that run. Then replace the shingles.

OR, hire a reputable roofing contractor to do that for you. The bonus with a contractor should be that he/she will guarantee the work to some extent.

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    BONUS ANSWER- dude you need to get in the attic space to see the cause of that bulge. No sense in disturbing it from the top unless it's leaking. Sep 1, 2020 at 18:57

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