In a medium bowl, stir together the first five ingredients (flour, sugar, cocoa powder, cocoa-chile blend or chipotle chile pepper, and ground cinnamon).
Using a pastry blender or your fingers, cut in the butter until the mixture resembles fine crumbs and starts to cling together.
Gather the mixture into a ball, kneading gently until it becomes smooth.
On a lightly floured surface, roll out the dough until it's about 1/4 inch thick.
Use a 1.5 to 2-inch fluted round or star-shaped cookie cutter to cut out the dough.
Place the cutouts about 1 inch apart on an ungreased extra-large cookie sheet.
Bake for 15 to 18 minutes or until the centers are firm.
Remove from the oven and let the cookies cool on wire racks.
For the Chocolate Glaze:
In a small bowl, stir together the powdered sugar, unsweetened cocoa powder, and, if desired, the ground cocoa-chile blend or a dash of ground chipotle chile pepper.
Stir in the softened butter.
Stir in enough milk (2 to 3 teaspoons) to reach a drizzling consistency.
Drizzle the glaze over the cooled cookies and let it stand until the glaze is set.
Notes / Tips / Wine Advice:
This recipe makes approximately 24 servings, with one cookie per serving.Storage:To store your Spicy Chocolate Shortbread Cookies, layer them between sheets of waxed paper in an airtight container. You can keep them at room temperature for up to 3 days or freeze them for up to 3 months. Enjoy!