no

Thank you, Christopher Nelson!!

Ahh. Just realized I worded the question differently in the title and the paragraph. Does the "no" refer to it's not okay to paint or it will not effect the caulk? Thanks again.

Is the caulk dirty? Probably is by now. Since it's been exposed for 4 years I wouldn't paint over it. I'd cut it out and replace it with a quality elastomeric caulk similar to DAP Dynaflex or SW Powerhouse caulk. If you decide to remove it and discover it's against bare wood, prime or paint the bare wood, let it dry, caulk, let it dry per label and then repaint.

I know that sounds like a chore, but if you paint it today, you'll most likely be removing it and repainting it next year.

Yikes, thanks, Brushworks.

Personally I would think it would be easier to clean the caulk .Brush makes a valid argument for replacing with a better grade caulking but we don't know what's there either.

They used Big Stretch. We have forced air and and cold dry winters so we knew there would be a lot of movement.