In ,
trader_4 belched:
I just finished some outside painting and am having a problem with
painter's tape that is sticking to new caulking around windows. It's
latex type caulk that was applied a couple weeks ago. Then painter's
tape was applied recently over it to mask off the windows. The caulk,
while cured enough for painting, etc, is apparently not cured enough
to keep it from bonding to the tape. I spotted this problem and even
switched to the lowest adhesion painter's tape for delicate surfaces.
Even so, after one to two days, it's sticking to the caulk underneath
and when you go to pull it off, it starts lifting the nice smooth
caulk job up with it. Doesn't seem to actually pull the caulk out of
a gap, but it does rough up what's there, make it stringy, a mess,
etc.

Any ideas on how to get it off? I tried using a hair dryer, no
effect. I tried removing it on mornings when it was cold, no effect.
I tried brushing on some mineral spirits, that might have helped a
little.
I even bought some Mossbacker's super special stuff that was highly
rated for removing tape, gum, etc. No effect. I think part of the
problem is that the tape now has paint over top of it too, so it's
harder for anything to penetrate. I was thinking of trying either
multiple coats of mineral spirits over a couple days or possibly
acetone? Of course one main concern is that I also don't want to
damage the new paint. The tape is just on the metal window frame,
but still some small amount of anything I use is going to get to the
very edge of the paint.

I would think this would be a common problem, caulking then taping,
painting is done a lot. But can't find anything about it. I guess
one way pro painters probably avoid it is by putting up two coats
of paint, same day, then removing the tape right away. But being
DIY, weather, etc, I've typically had at least 2 days between
putting it on and taking it off.

Any ideas?

Try some naptha, I also use WD-40 to remove spray adhesive from my hands, so
you might even try some of it or just kerosene