A.Jon Tobey, a painting contractor in Monroe, Wash., responds: Cedar — and red cedar in particular — has the reputation of being a wood that doesn't hold paint well. When red cedar is milled, the wood fibers at the surface get burnished and can form a resinous "mill glaze" that resists paint penetration. To remove it, use a garden sprayer to spray on a deck wash, then hose off the residue with fresh water. Be sure to clean both sides of each shutter, because if paint starts peeling on the back, it will eventually work its way to the front.

After the shutters have thoroughly dried, prime them with a high-quality latex primer. Next, if you're top-coating in a light color, spray a very light fog coat of a stain-blocking alkyd primer on the front of the shutters. This extra step prevents any remaining tannins in the cedar (which are water-activated) from bleeding through light-colored...

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