Preheat the convection oven to 325 degrees F. Line a cupcake pan with 24 cupcake liners.
In a mixing bowl, add the sugar, vanilla and eggs, and mix until combined. With the mixer on low speed, add the milk and oil, and mix until well combined.
In a separate bowl, add the flour, cocoa powder, baking powder, baking soda and salt, and mix together. Add the dry ingredients to the egg mixture and mix on medium speed until the batter is smooth, about 2 minutes. Turn off the mixer and add the hot coffee. Mix on low for 2 minutes more.
Fill the lines three-quarters full with batter and bake for 14 minutes. Once completely cooled, use a paring knife to cut out the center of the cupcake.
To assemble: Using a small ice cream scoop, fill the cupcakes with 1 scoop of the cooled Chocolate Truffle Ganache. Using a piping bag with a 1M tip, generously frost the cupcakes with Whipped Chocolate Buttercream, making sure to cover the filled area.
Chocolate Truffle Ganache:
Add the boiling cream to the chips and stir together until chips are completely melted. Add liqueur, mix well and set aside to cool.
Whipped Chocolate Buttercream:
In an electric mixer, beat the butter on high for 2 minutes. Once the butter is whipped, add the powdered sugar 1 cup a time until well blended. Add the vanilla and mix well. Add the cocoa powder and blend on medium speed until well incorporated. With the mixer on low speed, slowly add the heavy cream. Once the heavy cream is incorporated, turn the mixer on high and whip for 3 to 4 minutes.
This recipe was created by a contestant during a cooking competition. It has not been tested for home use.