Preheat the oven to 350°F.
In a large bowl, cream the butter and sugar. The mixture will be light and fluffy and well combined. Mix in the egg and vanilla extract until it is smooth.
To the wet ingredients, slowly add the flour, cocoa, baking powder, baking soda, and salt. Beat until combined. The dough will be dry and almost crumbly.
Using a cookie scoop, make 1 tablespoon (size 00) balls out of the dough, roll them in sanding or white granulated sugar, and place them on a parchment-lined cookie sheet.
Drain one 10-ounce jar of Maraschino cherries. Reserve the juice and set it aside for later. Pat cherries until very dry. If cherries are extra-large, cut them in half. Press a cherry into the center of each dough ball. Do not be afraid to press firmly.
Place in the preheated 350°F oven and bake until the cookies are set, 10-12 minutes. Once the cookies are baked, remove them from the oven. Allow the cookies to cool for 5 minutes and then frost while warm.
While the cookies are baking, heat the heavy cream until it begins to simmer. Once it is simmering, pour the cream over the chocolate chips. Allow the cream to melt the chocolate for 3 to 5 minutes. Once the chocolate is melting, slowly stir the mixture until it is smooth. Once the chocolate is smooth, add 1 tbsp of the reserved cherry juice. Note: As the chocolate cools, it will solidify. To soften, simply warm in the microwave for 10 seconds and stir.
Once the ganache has cooled slightly and thickened, spoon 1 to 2 teaspoons of frosting onto the top of each baked warm cookie, covering the cherry. Sprinkle with sugar or decoration, if desired.
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