Stir together flour, cocoa, baking soda, baking powder, and salt in a bowl.
In a stand mixer, cream together butter in sugar until light and fluffy.
Agg egg and vanilla, and beat thoroughlly.
Slowly add flour mixture to butter mixer until well blended. Dough should resemble playdough and slightly sticky. Put bowl in fridge to chill while you make the frosting.
In a saucepan over medium low heat, add sweetened condensed milk, chocolate chips, and 4 tsp cherry juice. Stir until chocolate has melted. Keep on low heat until ready to use.
Remove dough from fridge and roll into 1" balls. Place on a parchment lined cookie sheet. Use thumb to press hole in middle of dough.
Add 1 cherry to each cookie dough hole. Cover with 1 tsp ish of frosting, ensuring that cherry is covered by frosting.
Put in the middle of a 350°F oven for 10 minutes.
Remove from heat and garnish with a festive sprinkle or leave as is.