
Preheat oven to 350°F and line a standard 12-cup muffin tin with paper liners.
In a glass measuring cup or small bowl, whisk the hot coffee and cocoa powder together, then cover and let stand for 5 minutes.
In a medium mixing bowl, whisk together the flour, baking powder, baking soda, salt, and cinnamon.
In a large mixing bowl, whisk together the sugar, vegetable oil, and melted butter.
Add in the egg and whisk for twenty seconds, or until very well combined.
Add in the buttermilk, vanilla, and red food coloring and whisk to combine. Then whisk in the vinegar and coffee mixture.
Using a fine-mesh sieve, sift the flour mixture into the batter in three additions, whisking until each addition is incorporated. The batter will be thin.
Using a spring-loaded scoop, divide the batter evenly among prepared muffin cups. Lightly tap the bottom of the muffin pan against the counter several times to release any air bubbles.
Bake until cupcake tops are no longer sticky to the touch and a cake tester or toothpick comes out clean (about 17-20 minutes). It’s normal for the tops to look slightly spongy.
Let cupcakes cool in pan on a wire rack for 10 minutes before removing from the pan to cool completely (about 1 hour).
In the bowl of a stand mixer fitted with the paddle attachment, beat the softened butter and sifted powdered sugar on low. Gradually increase to medium-high to prevent a sugar cloud.
Beat for 3 minutes until smooth. (It may look dry at first, but it will come together like magic!)
Scrape down the bottom and sides of the bowl and paddle, then add the cream cheese and beat on medium-high for 1 minute until fluffy.*
Add the vanilla and beat for 30 seconds until fully incorporated. Scrape down the bowl again as needed.