I will be painting my house this summer which is painted cedar shakes. A previous owner calked cracks and also the spaces between the shakes. I have removed some of this caulk and paint as it is failing. Should I re-caulk the spaces between the shakes?

If the shakes were installed correctly they shouldn't need chaulk. Sounds like someone was really anal!

I Agree, You Don't Caulk Cedar Shakes, The Way The Shakes Are Laped , If Done Correctly Should Allow Any Water In , With Or Without Caulk, I Say Just Paint It As Is , But If Its Just A Few You Have To Recaulk Id Do It Just So They Match Back Up With The Rest

Also agreed, caulking shingles will not allow any moisture that does get behind them from evaporating, or draining causing mold and eventually decay

Thanks for all the great answers. Looks like I will be continuing to pull this caulk out. That must be why the paint (during the heavy NW rains this winter) the paint bubbled under the drip line and formed pockets filled with water!

Blackjack, you are correct, by caulking the shingles, there is no way for any moisture to escape and now you see the result. Hopefully there is no serious damage yet and you can correct this blunder.

If done correctly and using a elastromeric caulk it makes for a much nicer job. Over time the gap for cedar shakes will become larger. Using an elastromeric caulk will help close the gap. Very important to use a oil base primer first then caulk.

If the shingles have a 1'' offset on the seams there is no need for chalking. Between the tar paper(house wrap) and the under coarse you will have a good water shed.This is on 12'' revel.

On a 5'' or 6'' revel you will have 3 layers of shingles as shingle measure either 16'' or 18''.

Chuck