- 2 1/2 cups bittersweet chocolate chips (do not exceed 61% cacao; 15 to 16 ounces), divided
- 1 1/2 cups all purpose flour
- 1/4 cup natural unsweetened cocoa powder
- 1 teaspoon baking powder
- 1 teaspoon instant espresso powder
- 1/2 teaspoon salt
- 1/2 cup (1 stick) unsalted butter, room temperature
- 1 cup sugar
- 1 teaspoon vanilla extract
- 1 teaspoon peppermint extract
- 2 large eggs
- 4 candy canes or 16 red-and-white- striped hard peppermint candies, coarsely crushed
- Preheat oven to 375°F. Line 2 large rimmed baking sheets with parchment paper. Stir 2 cups chocolate chips in medium metal bowl set over saucepan of simmering water until melted and smooth. Measure 2/3 cup melted chocolate; transfer to small metal bowl and reserve for drizzling.
- Whisk flour, cocoa powder, baking powder, espresso powder, and salt in medium bowl. Using electric mixer, beat butter in large bowl until creamy. Add sugar and both extracts; beat until smooth. Add eggs; beat to blend. Beat in melted chocolate from medium bowl. Add dry ingredients; beat just to blend. Stir in remaining 1/2 cup chocolate chips. Measure 1 level tablespoonful dough; roll dough between palms to form ball. Place on prepared baking sheet. 3. Repeat with remaining dough, spacing cookies 1 1/2 inches apart.
- Bake cookies until cracked all over and tester inserted into center comes out with large moist crumbs attached, 8 to 9 minutes. Cool cookies on baking sheet 5 minutes. Transfer cookies on parchment paper to racks to cool completely.
- Rewarm reserved 2/3 cup chocolate over small saucepan of simmering water. Using fork, drizzle chocolate over cookies. Sprinkle crushed candy canes over, arranging some pieces with red parts showing. Chill just until chocolate sets, about 20 minutes. DO AHEAD: Can be made 3 weeks ahead. Store airtight in freezer. Bring to room temperature before serving.