To Caulk or Not To Caulk

I have an older home (1929) with wood column bases setting directly on concrete. I think the wood is cypress or similar dense wood. I have been caulking around the column bases, but the caulk always fails eventually by pulling away from the concrete. This makes me think all the caulk does is trap moisture between the wood and concrete and creates an unfavorable condition for the wood.

Is it better to not caulk so that water can drain out or evaporate?

I have a similar condition with the wood window sills on stone, but I assume caulking is needed there to reduce air infiltration.

 

If the bottom of the columns look ok without caulk, I'd leave them uncualked. The window should stay caulked both to prevent air infiltration and rain water.

 

When caulking between the wood window sills and the stone, I have always used a good latex acrylic caulk, but my experience is that the caulk always pulls away from the stone eventually. I suspect the stone absorbs moisture which causes the caulk to loosen. I now wonder if the stone should be sealed with something before I caulk.

Any suggestions?

 

I talked to a tech at a caulk manufacturer and he recommended their paintable advanced polymer...something called a siliconized polyether. So it was off to the Depot where I also got some cleaner and a special stainless steel brush that looks something like a tooth brush but with arched handle and a second smaller set of bristles on the top for getting into the corners easily. I scrubbed the stone and flushed with clear water. Now I am waiting for it to dry so I can try the new caulk which by the way requires mineral spirits for cleanup.

I should be able to give you a report in a few years.