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Exterior paint and caulk guidance

Rob Yocum
last month

I have a porch where small ~2"x2'' vertical painted posts join against a 2"x8" horizontal painted board. Unfortunately, the posts don't sit flush against the board and its a bit unsightly (see picture). The OCD in mean wants to caulk around the posts, but I'm worried about the inevitable case where water seeps in and can't get out. What do you suggest that I do? Leave as is? Caulk/paint around three sides?

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