Preheat oven to 350 degrees.
In a large mixing bowl, or the base of a stand mixer, cream the butter and sugar. Add egg and vanilla and mix well.
In a smaller bowl, combine the flour, cocoa, ¼ tsp. of salt, baking powder, and baking soda.
Slowly add the dry mixture to the creamed mixture and mix until fully combined.
Remove cherries from jar and set on a plate lined with a paper towel, reserving 1 ½ tsp. of the juice. Pat cherries dry.
Take about 1 tablespoon of dough, roll it into a ball in your hand and then flatten to about ¼ to ½ inch thick. (You want it to be thick enough that it will not break in the next step).
Place a cherry in the center of the dough circle and wrap the dough completely around the cherry to form a ball.
Place the cookies 2 inches apart on an ungreased cookie sheet.
Bake at 350 degrees for 8-10 minutes until set. Place on a wire rack to cool completely.
For the frosting, heat the chocolate chips and sweetened condensed milk in a small saucepan until the chips are melted. Stir until smooth. Remove from heat and add reserved cherry juice and remaining ¼ tsp. of salt.
Using a spoon, scoop the chocolate mixture on the cookies and spread out to evenly coat the top and sides of the cookies. You will want to work quickly; as the frosting cools it begins to set and becomes harder to work with.
