On Sat, 25 Jan 2020 13:03:47 -0500, 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. 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.
Actually the new caulking being used by quality window, door, and
siding installers will last AT LEAST 25 years - Mine has been 30 on
the upstairs windows and it's still pretty much the same as when it
was installed.

On a roof it won't last QUITE as long because of the heat etc - yet I
have a 25 year warranty on the flashing - including the caulk - on my
new roof.