Preheat oven to 350° F. Line baking sheets with parchment or silpats (see note). Set aside.
In a medium bowl, combine the dry ingredients (flour, cocoa, salt, baking powder, and baking soda). Whisk to combine. Set aside.
In the bowl of a stand mixer, cream the butter and sugar until light and fluffy. Scrape down the sides of the bowl.
Add egg, vanilla extract, and chocolate extract (see note). Mix to combine. If needed, scrape down the sides of the bowl again.
Add dry ingredients and mix until just combined. Using a small cookie scoop (see note), portion the dough into balls. Roll the dough between your palms to form smooth balls, placing them at least 2 inches apart on the prepared cookie sheets.
Create an indentation in the center of each dough ball using your knuckle or thumb (like you would with a thumbprint cookie). Place a single maraschino cherry (see note) in the center of each cookie.
For Frosting:
In a small saucepan, combine chocolate chips, sweetened condensed milk (see note), and cherry juice. Melt over low heat, stirring until smooth. If the frosting is too thick, add additional cherry juice a teaspoon at a time until the appropriate consistency is reached.
You will need to keep the frosting warm to keep it the appropriate consistency while you work. Cover each cherry with about 1 teaspoon of the frosting.
Bake the cookies for about 10 minutes, turning the baking sheets around at the halfway point. Allow cookies to cool on the pan for about ten minutes, then remove to a wire rack to cool completely.Enjoy!
Notes
Note on chocolate extract: I highly recommend this (sometimes overlooked) extract! It lends amazing depth of flavor to chocolate baked goods! If you can't find it in your local grocery store, you can find some [here]. Even better, make yourself some [Homemade Chocolate Extract] for next time!Note on maraschino cherries: Those deep, dark cherries aren't your average maraschino cherry. All natural and insanely delicious, they're pricey, but worth the splurge. You can find them online [here]. I didn't use quite the whole jar in the cookies. I'm sure you can find suitable use for any leftovers. ;)Note on sweetened condensed milk: I know, I know. A recipe calling for a half cup of sweetened condensed milk. If you don't have another recipe you'd like to use the rest in, it freezes well!Note on silpats: I use silpats (like this one [here]) when baking, which makes the cookies brown up a little slower. If you're lining your pans with parchment, your cookies will likely be done a bit sooner.Note on cookie scoop: I use a small cookie scoop to portion out my cookies so they're all uniform in size (and my hands stay a lot cleaner). I really like the one that I use: link [here].