Does anyone know of a way to paint over “non-paintable” caulk?

Karen Riemersma
by Karen Riemersma

Our house has wood siding which has been repainted 2-3 times. Unfortunately, somewhere along the way a lot of caulking was done using non-paintable silicone caulk around windows and other areas where wood meets wood. We’ve always used the same latex house “stain” (a thick paint that needs no primer) from Sherwin Williams. It takes about 4 coats to cover the caulk but it’s not really attached to the wood...just “floats” on top and soon starts peeling off of the caulked areas. Any suggestions other than trying to remove all that caulk and replacing it with paintable caulk?

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