Chocolate-Covered Cherry Shortbread Cookies

Step 1
Preheat the oven to 325 degrees F (165 degrees C).

Step 2
Finely chop 6 ounces baking chocolate and set aside.

Step 3
Combine flour, cold butter, 1/2 cup sugar, and cocoa powder in a large bowl; beat until mixture resembles small crumbs. Stir in chopped chocolate, maraschino cherries, and almond extract until well combined.

Step 4
Pour 2 tablespoons sugar into a shallow bowl. Form cookie dough into 1-inch balls and roll in the sugar until coated. Arrange cookies 1 inch apart on a cookie sheet. Use the bottom of a cup to flatten cookies to 1 1/2-inch rounds.

Step 5
Bake in the preheated oven until edges are firm, about 10 minutes. Let cool on the cookie sheet for 2 minutes. Carefully transfer cookies to waxed paper; let cool completely, at least 1 hour.

Step 6
Heat remaining chocolate in a small pot, stirring occasionally, until melted. Add 1 tablespoon butter and milk; stir until mixture is melted and runs off a spoon with ease. Add another tablespoon of butter and milk if needed.

Step 7
Dip each cookie at least halfway into the melted chocolate mixture. Lay the dipped cookies back on the waxed paper. Let cool and harden for several hours.