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

Finely chop 6 ounces baking chocolate and set aside.

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.

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.

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.

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.

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.