1 1/2 c. flour
1/2 c. cocoa powder
1/4 tsp. baking powder
1/4 tsp. baking soda
1/4 tsp. salt
8 Tbl. (1 stick) butter, softened
1 c. sugar
1 large egg
1 1/2 tsp. vanilla extract
1 c. semisweet chocolate chips
1/2 c. sweetened condensed milk
2 (12 oz.) jars maraschino cherries, drained and stemmed, 2 Tbl. juice reserved
Whisk flour, cocoa, baking powder, baking soda, and salt in bowl; set aside. Beat butter and sugar until light and fluffy, about 2 minutes. Beat in egg and vanilla until incorporated. Reduce speed to low, add flour mixture, and mix until dough forms, about 1 minute.
Heat chocolate and milk in saucepan over low heat until chocolate is melted, about 5 minutes (mixture should have the consistency of mayonnaise). Off heat, stir in reserved cherry juice. Cover and keep warm.
Heat oven to 350 degrees. Roll dough into 1-inch balls and place 2 inches apart on baking sheet. Using thumb, make an indentation in the center of each cookie. Place 1 cherry in center of each cookie, then top with 1/4 - 1/2 tsp of warm chocolate mixture (you want it to cover the cherry, but not necessarily running off of the cookie onto the sheet). Bake until cookies are just set, 10-12 minutes.