In a large bowl, whisk together the flour, cocoa powder, salt, baking soda, baking powder and espresso powder. Set aside.
In the bowl of a mixer, beat together the butter and sugar until light and fluffy.
Add the egg and vanilla. Beat to combine.
Slowly add the dry ingredients to the butter mixture and stir to combine.
Roll the dough into 1 inch balls and place on a cookie sheet lined with parchment. Press the center of each ball down with your thumb to form a well. Set aside.
In a small saucepan, melt the chocolate until smooth and stir in the sweetened condensed milk. Add the maraschino juice and stir to combine.
Place a cherry in the center of the cookie and spoon 1 tablespoon of the chocolate sauce over the cherry to cover. Repeat with remaining cookies.
Bake the cookies for 10 minutes.
Transfer the cookies to a rack to cool completely to room temperature before moving to an airtight container. Or enjoy immediately.