1/2 cup plus 2 teaspoons all-purpose flour
3 tablespoons unsweetened cocoa powder
1 cup plus 1 tablespoon sugar
5 tablespoons unsalted butter, room temperature
1 1/2 teaspoons vanilla extract
Preheat the oven to 350°F. Line 2 rimmed baking sheets with parchment paper or use sil-pat liners. Melt the chocolate in the microwave at 50% power in 30-second intervals or in the top of a double boiler. Let the chocolate cool 10 minutes.
Meanwhile, sift together the flour, cocoa powder, cinnamon, ancho powder, baking powder, and salt into a bowl. Using an electric mixer on medium speed, beat the sugar and butter in another medium bowl until crumbly. Add the eggs, 1 at a time, beating well after each addition. Continue to mix on medium speed until the mixture is light, pale, and creamy, about 5 minutes. Add the melted chocolate and vanilla and beat just until blended. Fold in the dry ingredients, then fold in the chocolate chips.
Drop the cookie dough by 1/4 cupfuls (or use a #20 ice cream scoop) onto prepared baking sheets, spacing 2 inches apart. Bake cookies, 1 baking sheet at a time, until tops are evenly cracked but cookies are not yet firm to touch, about 16 minutes. Let the cookies cool completely on baking sheets before storing. Store in an airtight container up to 3 days.