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 paints. Then finish up with a top-quality, 100 percent acrylic latex paint (I recommend Sherwin-Williams' Duration), probably in a semigloss to make the shutters really pop.

If you have a lot of shutters to paint, three coats may seem like an excessive amount of work. But with an airless sprayer (available at most rental stores), you can spray three coats on 50 shutters in a day. In any case, you definitely want to spray — rather than brush on — the alkyd primer, because if you apply anything more than a slight fog, the brittleness will lead to cracking and create problems that far outweigh any benefits.

If spray equipment isn't available, buy a few rattle cans of the alkyd primer and just lightly dust the shutters for this step, even if you're brushing the other coats. With modern paints, if you prep and paint right the first time, you'll never have to do it again.