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Drain maraschino cherries, reserving juice. Remove stems from cherries. If using a half cherry, slice cherries in half.
Mix butter with a mixer until soft and smooth
Add sugar and beat for 3-4 minutes until light and fluffy
Stir in eggs
Add cherry juice and vanilla
In a separate bowl, combine flour, cocoa powder, baking powder, baking soda and salt
Add flour mixture to mixing bowl and mix until well combined
Cover and refrigerate for at least 30 minutes
When ready to form cookies, place sweetened condensed milk and chocolate chips in a saucepan on medium low heat.
Stir just until chocolate is melted. Remove from heat and stir in cherry juice.
Using a small cookie scoop (#60) or your hands, form small round balls of dough. Place on an ungreased baking sheet about 1 inch apart. The dough is sticky so you may need to rinse your cookie scoop with cold water a few times while forming cookies.
Place an indentation in the center of each cookie. Add a ½ of a cherry in the indentation.
Top with chocolate frosting mixture fully covering cherry
Bake in a preheated 350°F oven for 10 minutes
Allow cookies to cool for a minute on baking sheet. Then remove and finish cooling on a cooling rack.