Preheat the oven to 350°F (180°C) or 160°C if using a fan oven. Line three baking sheets with parchment paper and set aside.
In a medium bowl, whisk together the flour, cocoa powder, baking soda, salt, and baking powder until evenly mixed; set aside.
In a separate large mixing bowl, cream the butter, brown sugar and granulated sugar until smooth, about 2-3 minutes. Add the eggs, maraschino cherry liquid, and vanilla extract and beat on medium speed until fully incorporated.
Add the flour mixture to the butter mixture in 2-3 separate additions, mixing well after each.
Divide the dough into 25 golf ball sized dough balls, then place on the prepared baking sheets 3 inches apart. Gently press a cherry into the center of each cookie, then bake in the preheated oven for 9-11 minutes, or until they are spread and puffed up.
Meanwhile, melt the chocolate chips and the shortening in a microwave safe bowl in 30 second intervals in the microwave until fully melted and smooth, mixing well after each microwave.
Allow the cookies to cool completely before drizzling with the melted chocolate.
Notes
Measuring Flour: Adding too much flour to the dough will make it dry and dense. When measuring flour, spoon it into the measuring cup and level it off with a knife.
Adding Cherries: It can be helpful to use your thumb to create a shallow indent for the cherries to sit. Then you can call these cookies chocolate cherry thumbprints!
The Chocolate Topping: Adding shortening to melted chocolate helps to keep it from hardening too firmly. The chocolate drizzle will stay somewhat soft. If you want the drizzle to be more sturdy, you can leave out the shortening.
Add Decorations: Red or white sprinkles would be beautiful on these cookies, making them festive enough for Christmas or Valentine's Day parties. Be sure to add the sprinkles to the chocolate drizzle before it can harden.
Store At Room Temperature: Because the chocolatey topping is semi-soft, these cookies will store best in a single layer in an airtight container and can be kept at room temperature for up to 3 days. After that, the cookies will start to harden.
Store In the Freezer: It's best to flash-freeze these cookies by freezing them on a cookie tray until they're firm, then transferring the frozen cookies to an airtight container. Keep them in the freezer for up to 3 months. Before serving, remove them from the container and arrange in a single layer on a plate. Allow to thaw at room temperature.