Preheat the oven to 350°F and line a large baking sheet with parchment paper and set aside. If you only have a 9x13-inch baking sheet, you'll want to use two baking sheets.
In a medium bowl, whisk together the flour, cocoa powder, powdered milk, espresso powder, corn starch, salt, and baking soda. Set aside.
1½ cup all-purpose flour, ½ cup unsweetened cocoa powder, 1 teaspoon espresso powder, 2 teaspoons cornstarch, ¾ teaspoon salt, ¼ teaspoon baking soda, 1 tablespoon powdered milk
Partially melt the shortening in a microwave-safe bowl. I melt mine for 45 seconds, you want it to just be pooling a bit but still have a decent amount of stick left.
½ cup vegetable shortening
Add the butter and sugars to a large bowl or stand mixer fitted with a paddle attachment and cream just until smooth.
½ cup light brown sugar, ½ cup granulated sugar
Add in the egg and vanilla extract and beat until fully incorporated.
1 large egg, 1 teaspoon pure vanilla extract
Add half of the dry ingredients to the wet ingredients and beat just until incorporated. Then add the remaining dry ingredients and the milk and mix until thoroughly combined.
2 tablespoons whole milk
Portion the dough into 10 even portions (about 2.3oz. each) and gently press your thumb into the middle of the ball to create a well. Place a cherry cordial in each well and gently use your hands to work the dough up and around the sides and top of the cordial and pinch and roll to seal.
10 Cherry Cordials
Place the cookies on the baking sheet, trying to keep the cordial upright. Place cookie dough at least 2 inches apart on the prepared baking sheet (they don't spread a ton). Bake for 8 to 9 minutes until the edges are just set. The cookies will look slightly underdone; this is normal as they will continue to cook and firm up as they cool.
Allow the cookies to cool on the pan for 15 minutes before transferring them to a wire rack with a spatula to cool completely. These cookies are very soft right after baking and will firm up while they cool.
Once cooled, melt the chocolate melting wafers in the microwave at 30-second intervals, stirring between each one until fully melted. Transfer to a piping or ziploc bag and cut the corner off and drizzle over the tops of the cookies and then top with sprinkles if desired.
¼ cup chocolate melting wafers, 1 tablespoon sprinkles