Chocolate-Covered Cherry Cookies
With your electric mixer, beat the butter and 1 cup sugar on medium speed until light and fluffy, about 5 minutes. Beat in the egg and vanilla until well combined.
In a separate bowl, combine the flour, cocoa, baking soda, baking powder and salt. Add the flour mixture by spoonfuls to the batter, mixing just until combined. If the dough seems too dry, add 1-2 tablespoons milk or coffee to bring the dough together.
Roll the cookie dough into 1 1/2 inch balls (about 36 balls) and roll each cookie ball in the 1/4 cup sugar. Using the back of a 1-teaspoon measuring spoon, press an indentation in the center of each cookie. Place cookie balls on a baking sheet and freeze until firm, about an hour.
Preheat the oven to 350 F. In a small saucepan, combine the chocolate chips and sweetened condensed milk; warm over medium-low heat until the chocolate is melted, stirring mixture occasionally until smooth. Stir in 4 tablespoons cherry juice.
Working in batches (keeping cookie balls in the freezer until you're ready to bake them) place the frozen cookie balls 2 inches apart on an ungreased baking sheet. Place a cherry in the indentation of each cookie. Spoon a small amount of frosting (about a teaspoon) over each cherry, letting it drip down to cover the cherry. (Keep frosting covered with plastic wrap in between batches to keep it from drying out.)
Bake cookies for 7 minutes. Remove from oven, cool for 1 minute on the baking sheet, then transfer to a wire rack to cool completely.
If you have any frosting left after baking all the cookies, you can drizzle this over the cookies and add some decorative sprinkles (although the frosting will take much longer to set this way, whereas it comes out of the oven perfectly set).
Alternatively, you can fill the cookies with jam, or top the cherries with a small dab of Nutella.Yields 3 dozen cookies.