Preheat the oven to 325 degrees F. Line cupcake or muffin pans with 24 cupcake liners.
In the bowl of a stand mixer with a paddle attachment, combine the buttermilk, oil, vanilla and eggs. In a separate bowl, sift the granulated sugar, flours, cocoa powder, baking soda, baking powder and salt. Slowly add the dry ingredients into the wet ingredients and mix until just combined.
Mix the hot water and espresso powder in a pitcher, and slowly stir into the mixing bowl. Fill the cupcake liners and bake for 20 minutes, rotating halfway through. Remove from the oven and cool completely before frosting.
Fill the cupcakes with Chocolate Chipotle Truffle Filling. Frost with Chocolate Buttercream.
Heat the cream until simmering over medium heat. Place the semisweet chips in a glass bowl and pour the hot cream onto the chips. Allow to sit for a minimum of 2 minutes. Transfer the chocolate cream mixture to a stand mixer outfitted with the whisk attachment. Add in the chipotle powder. Whisk on medium speed until light and fluffy.
In the bowl of a stand mixer fitted with the paddle attachment, whip the butter and cocoa until incorporated. Slowly add in the powdered sugar, heavy whipping cream and vanilla. Whip until fluffy.
This recipe was created by a contestant during a cooking competition. It has not been tested for home use.