Preheat oven to 350 degrees.
Line baking sheets with parchment paper.
In a large bowl, sift together flour, cocoa powder, baking powder, baking soda and salt. Set aside.
With your mixer, cream together butter and sugar until light and fluffy, about 2-3 minutes.
Add in egg and vanilla and mix to combine.
Slowly add in dry mixture and mix until everything is well combined.
Use paper towels to pat the cherries, removing any excess liquid.
If dough feels too sticky - refrigerate for 30 minutes before rolling them into balls.
Use 1 tablespoon of cookie dough and use your hands to roll them into balls. Arrange on baking sheets, about 2 inches apart. Use your thumb to gently create an indentation in the center of the cookie.
Place a Maraschino cherry in the center of each cookie. Bake for 10-12 minutes, or until cookies are just set.
As the cookies are baking, create the chocolate topping. In a large bowl combine 1 cup milk chocolate chips with 1/2 cup sweetened condensed milk and 2 tablespoons cherry juice. Microwave at 50% power for about 1 minute, then stir. Then microwave 20 seconds at a time until the chocolate is melted and well combined, stirring between each interval.
When the cookies are done baking, carefully transfer them to cooling racks to cool for a few minutes.
Place the chocolate mixture in a piping bag, or a Ziplock bag. Snip the corner and pipe the chocolate mixture over the center of each cookie. Allow the chocolate to firm up which will take about 15-20 minutes.
You’ll get 2.5-3 dozen cookies from one batch.