Begin with 1/2 cup butter in a mixer.
Add 1 cup sugar.
Add 1 large egg.
Mix butter, sugar, and egg until creamy. Add 1 teaspoon vanilla.
Stir together 1 1/2 cup flour, 1/2 cup cocoa, 1/4 teaspoon salt, 1/4 teaspoon baking powder, and 1/4 teaspoon baking soda.
Add dry ingredients slowly to creamy mixture. Beat until combined.
The dough will be somewhat dry and almost crumbly.
Make 1-inch balls out of dough. Place on cookie sheet. Try baking on silicone pads. Clean-up is a breeze!
Drain one 10-ounce jar of Maraschino cherries. Preserve the juice and set aside for later!
Pat dry cherries until very dry. If cherries are extra-large, cut in half.
Press cherries into center of dough balls. Do not be afraid to press firmly!
In microwave safe bowl, melt 1 cup semi-sweet chocolate chips and 1/2 cup sweetened condensed milk, in increments. Add extra cherry juice to thin to a spreadable consistency (about 3 teaspoons).
Spoon 1 teaspoon of frosting on each unbaked cookie.
Place in oven and bake for 10 to 12 minutes at 350 degrees.
Cookies will spread during baking and frosting will even out.
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