On Saturday, January 25, 2020 at 1:02:15 PM UTC-5, Gary wrote:
micky wrote:

If it's the caulk, it's been there for 13 years. How come no drip into
the 2nd floor until this year?

What I see in that picture... weep holes are clear. It's the bad
caulking between shingles and flashing. All those gaps will let
water in. Where the roof is buckled, I see no caulking at all.

I would get someone up there to recaulk that line asap.

It's not supposed to be caulked to begin with. The roofer was a hack.


Fix the
buckled part later if you want to wait. For now, stop the leaks.
Recaulk it and check the other side too.

Note: No caulking outside will hold up for 13 years. With an
important thing like a roof, get that caulking checked and
repaired once a year or two.

A roof done properly does not rely on caulking to begin with.