Preheat oven to 350°F and line at least 2 cookie sheets with parchment paper.
Drain the cherries and reserve the liquid. Cut the cherries in half and set aside. You may have to quarter some of the cherries depending on how many are in the can.
In the bowl of stand mixer fitted with paddle attachment or with a large bowl and hand mixer, cream together the softened butter and granulated sugar until light and fluffy. This will take 2-3 minutes.
Add the eggs, one at a time, beating well after each addition and scraping the sides and bottom of bowl as needed.
Beat in the vanilla extract.
Add the cocoa powder, baking powder, baking soda, salt and all purpose flour. Mix on low speed just until everything is fulling combined. Scrape the bottom of the bowl to ensure everything is completely blended.
Using a small cookie scoop or a level tablespoon, scoop dough and place 2 inches apart on cookie sheets. Roll each scoop into a smooth ball and then make an indent with your thumb or a teaspoon measuring spoon in the center. I like to use the teaspoon because it makes a perfect indent.
Place a halved cherry in each cookie.
In a microwave safe bowl, combine the chocolate chips and sweetened condensed milk. Microwave in 30 second intervals stirring after each one until the chocolate chips are completely melted and smooth.
Stir in 3 tablespoons of the reserved cherry juice to the chocolate sauce.
Dollop about a teaspoon or so of sauce on top of the cherry pieces.
Bake cookies in preheated oven for 8-10 minutes until cookies look set.
Let cookies cool on pan for 10 minutes and then carefully remove to wire rack to cool completely.