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Preheat oven to 350°F. In a small saucepan, add Guinness and bring to a simmer over medium heat. Continue to simmer until the beer reduces to 1/2 cup. Remove from the heat and set aside to cool.
In a large bowl combine flour, cocoa, baking soda, baking powder, and salt, whisk to combine. In the bowl of a stand mixer, fitted with the whisk attachment, place reduced Guinness, olive oil, sugar, eggs, sour cream, and vanilla, whisk until blended and smooth. Begin adding in the dry ingredients, a cup full at a time, until the batter is smooth and blended.
Fill a muffin tin with decorative paper baking cups and fill 3/4 of the way full with batter. Bake cupcakes for 20-30 minutes, until cooked through. Remove them from the oven and set them aside to cool. Once the cupcakes have cooled completely, top with frosting (either spreading or piping the frosting on top of the cupcakes).
Place butter in the bowl of a stand mixer, fitted with the paddle attachment, and beat or cream until smooth. Replace the paddle attachment with the whisk attachment (removing as much butter from the paddle as possible) and begin whisking in the powdered sugar, 1 cup at a time, until combined. Add balsamic, vanilla, cocoa powder, and milk, and continue to whisk until fluffy and smooth.
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