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For the Cupcakes:
For the Frosting:
Preheat your oven to 350 Degrees F and line a muffin pan with paper liners, then spray the top of the pan with cooking spray
Put the vegetable oil and chocolate chips in a heatproof bowl and microwave for 30 seconds, then stir to combine.
Combine the flour, sugar, cocoa, baking powder, baking soda, and salt in a large bowl with a whisk, then add in the chocolate and oil mixture along with the buttermilk, eggs, 1/4 cup bourbon, and vanilla.
Gently stir until just combined, and use a 2 3/4 inch cookie scoop, or a spoon, to fill each cupcake liner 2/3 of the way full. Tap the pan on the counter to release any air bubbles in the batter once it is all distributed.
Bake for 18-20 minutes, until a toothpick inserted into the center comes out clean. Allow to cool completely.
Make the frosting by creaming the butter in a bowl with a hand mixer for 3 minutes, until very light and fluffy. Add the caramel and vanilla and mix for another minute until smooth.
Add the powdered sugar, mix on a low speed to combine, then mix on a high speed for one minute, until light and fluffy.
Pipe or spread the frosting on top of the cooled cupcakes, then top with chocolate shavings or chocolate chips.
Original recipe courtesy of AJ DeDiego
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