Preheat the oven to 350 degrees F (180 degrees C).
Beat sugar and butter together in a large bowl with an electric mixer until light and fluffy.
Add egg and vanilla; beat well.
Stir in flour, cocoa powder, salt, baking soda, and baking powder until smooth.
Roll dough into walnut-size balls and place 2 inches apart on ungreased cookie sheets.
Make an indentation with your thumb in the center of each cookie.
Drain cherries and reserve juice. Place a cherry in the indentation of each cookie ball.
Combine chocolate chips with condensed milk in a saucepan over low heat; stir until chocolate is melted.
Stir in 4 teaspoons of cherry juice.
Drizzle or spoon about 1 teaspoon of chocolate cherry mixture over each cherry to cover.
Bake in the preheated oven for 10 minutes.
Cool on the baking sheets briefly before removing to a wire rack to cool completely.
