- 1 1/2 cups all-purpose flour
- 2 tablespoons unsweetened cocoa powder
- 1/8 teaspoon baking powder
- 6 ounces unsweetened chocolate (not bittersweet)
- 1 stick (1/2 cup) unsalted butter
- 1 cup sugar
- 2 large eggs
- 1 teaspoon vanilla
- parchment paper for lining baking sheets
- 8 small candy canes (about 2 1/2 ounces total)
- Into a bowl sift together flour, cocoa powder, and baking powder. Chop chocolate and in a small heavy saucepan melt with butter over very low heat, stirring until smooth. Remove pan from heat and stir in sugar. Transfer chocolate mixture to a large bowl and cool 10 minutes. Stir in eggs and vanilla until just combined. Stir in flour mixture until just combined.
- Halve dough and roll out each half between sheets of wax paper into an 11 1/2-inch round (about 3/16 inch thick). Remove top sheet of wax paper from each round and with a 1 1/2-inch round cutter cut rounds, leaving all of dough on wax paper. Cut a 3/4-inch-diameter hole (we used wide end of a pastry tip) in center of half of rounds. (Do not remove any of cut-outs from dough; keep rounds intact on wax paper). Replace sheets of wax paper and stack dough on a baking sheet. Chill dough until firm, at least 4 hours, and up to 3 days.
- Preheat oven to 350°F and line 2 large baking sheets with parchment paper. Finely chop candy canes. Transfer dough rounds, still between sheets of wax paper, to a work surface. Remove top sheet of wax paper from each dough round. Replace wax paper loosely and flip over each wax-paper-enclosed dough round. From each dough round remove and discard sheet of wax paper now on top (this process prevents cookies from sticking to wax paper). Lift cut-out centers and scraps from wax paper and reroll them to make more 1 1/2-inch solid rounds and rings in same manner, chilling until firm. Center rings on top of solid rounds and fill each center with about 1/4 teaspoon chopped candy cane.
- Arrange cookies about 1/2 inch apart on baking sheets. Bake cookies in batches in lower third of oven 8 minutes, or just until candy begins to melt (not liquefy). With a spatula transfer cookies to racks to cool completely. Cookies keep, layered between sheets of wax paper in airtight containers at room temperature, 1 week.