In a medium saucepan, combine the pitted 1 lbs fresh cherries, 1 tbsp lemon juice, 1 tsp vanilla extract, 1 tbsp bourbon, and 3/4 cup granulated sugar.
1 tsp vanilla extract, 1 lbs fresh cherries, 1 tbsp lemon juice, 1 tbsp bourbon, 3/4 cup granulated sugar
Cook over medium heat, stirring occasionally, until the cherries release their juices and the mixture begins to thicken, about 10-15 minutes.
Once the filling is thickened and syrupy, remove it from the heat and let it cool to room temperature.
Preheat your oven to 350°F (175°C) and line a cupcake tin with paper liners.
In a medium bowl, whisk together the 1 cup cake flour, 1/2 cup cocoa powder, 1 1/2 tsp baking powder, and 1 tsp salt. Set aside.
1 cup cake flour, 1/2 cup cocoa powder, 1 1/2 tsp baking powder, 1 tsp salt
In a large bowl, beat the softened 1/2 cup salted butter and 1 cup granulated sugar together until light and fluffy, about 3-4 minutes.
1/2 cup salted butter, 1 cup granulated sugar
Add the 2 eggs one at a time, beating well after each addition. Mix in the 2 tsp vanilla extract.
2 eggs, 2 tsp vanilla extract
Gradually add the dry ingredients to the butter mixture, alternating with the 3/4 cup whole milk, beginning and ending with the dry ingredients. Mix until just combined.
3/4 cup whole milk
Divide the batter evenly among the cupcake liners, filling each about 2/3 full.
Bake in the preheated oven for 18-22 minutes, or until a toothpick inserted into the center comes out clean.
Let the cupcakes cool in the tin for 5 minutes, then transfer them to a wire rack to cool completely.
In a large bowl, beat the softened 1 cup salted butter until smooth.
1 cup salted butter
Gradually add the 4 cups powdered sugar and 1/2 cup cocoa powder, mixing on low speed until incorporated.
4 cups powdered sugar, 1/2 cup cocoa powder
Add the 1/4 cup heavy cream and 2 tsp vanilla extract, then increase the speed to medium-high and beat until the frosting is light and fluffy. If the frosting is too thick, add a little more cream until you reach the desired consistency.
1/4 cup heavy cream, 1 tsp vanilla extract
Once the cupcakes have cooled completely, use a small paring knife to cut out a small cone-shaped piece from the center of each cupcake.
Fill each cavity with the cooled cherry filling.
Generously frost each cupcake with the prepared chocolate frosting.
Top each cupcake with a chocolate covered cherry.