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Preheat oven to 350°F. Drain cherries, reserving juice. Halve any large cherries. In a medium mixing bowl, beat butter with an electric mixer on medium to high speed for 30 seconds. Add sugar, baking powder, baking soda and salt. Beat until combined, scraping sides of bowl occasionally. Beat in egg and vanilla until combined. Beat in cocoa powder and as much of the flour as you can with the mixer. Stir in any remaining flour.
Shape dough into 1-inch balls. Place balls about 2 inches apart on an ungreased baking sheet. Press your thumb into the center of each ball. Place a cherry in each center.
In a small saucepan, combine chocolate pieces and sweetened condensed milk. Cook and stir over low heat until chocolate melts. Stir in 4 teaspoons of the reserved cherry juice. (If necessary, frosting may be thinned with additional cherry juice.) Spoon 1 teaspoon frosting over each cherry, spreading to cover.
Bake for about 10 minutes or until edges are firm. Cool on pan for 1 minute. Transfer to a wire rack and let cool.