1 cup organic powdered sugar, (I use Wholesome Sweeteners brand)
1 teaspoon natural vanilla extract
1 cup cocoa powder (I use Dagoba's cacao powder)
3/4 teaspoon fine grain sea salt
1 1/2 cups whole wheat pastry flour
Chocolate Peppermint Coating:
1 pound good quality semi-sweet chocolate, chopped
1/4 teaspoon plus a couple drops of natural peppermint extract (I use Flavorganics brand, avail. at Whole Foods)
Preheat your oven to 350. Racks in the middle zone.
Make the cookie dough: In a mixer cream the butter until it is light and fluffy. Add the powdered sugar and cream some more, scraping the sides of the bowl a couple times if necessary. Stir in the vanilla extract and then the salt and cocoa powder. Mix until the cocoa powder is integrated and the batter is smooth and creamy, sort of like a thick frosting. Add the whole wheat pastry flour and mix just until the batter is no longer dusty looking, it might still be a bit crumbly, and that's o.k. You don't want to over mix and end up with tough cookies.
Turn the dough out onto a counter, gather it into a ball, and kneed it just once or twice to bring it together into once nice, smooth mass. Place the ball of dough into a large plastic bag and flatten it into a disk roughly 3/4-inch thick. Place the dough in the freezer for 20 minutes to chill.
Rollout and bake: Remove the dough from the freezer and roll it out really thin, remember how thin Thin Mints are? That's how thin you need your dough, about 1/8-inch. You can either roll it out between two sheets of plastic, or dust your counter and rolling pin with a bit of flour and do it that way. Stamp out cookies using a 1 1/2-inch cutter (this time I used one with a fluted edge, I've done hearts and other shapes in the past). Place cookies on a parchment-lined baking sheet and bake for 10 minutes. Remove the cookies from the oven and allow them to cool completely on a baking rack if you've got one.
Make the peppermint coating:
While the cookies are in the oven you can get the coating ready. I use a makeshift double boiler to melt chocolate (a metal pan over a saucepan of gently simmering water), but I know many people who swear by melting chocolate in the microwave. Slowly melt the chocolate, stirring occasionally until it is glossy and smooth. Stir in the peppermint extract. If you think the chocolate needs a bit more peppermint kick, add more extract a drop or two at a time - but don't go overboard.
Finishing the cookies: You are going to coat the cookies one at a time and then gently set them on a parchment-lined baking sheet to set. Drop one cookie into the chocolate and (using a fork) carefully make sure it gets fully coated. Lift the cookie out of the chocolate with the fork and bang the fork on the side of the pan to drain any extra chocolate off the cookie. You are after a thin, even coating of chocolate. Place on the aforementioned prepared baking sheet, and repeat for the rest of the cookies. Place the cookies in the refrigerator or freezer to set. They will set at room temperature, it just takes much longer, and I prefer them straight out of the freezer anyways ;)
Make 3 or 4 dozen cookies.
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