Preheat oven to 350°F. Line 24 cupcake tins with cupcake liners. Set aside.
In a large bowl, whisk together sugar, cocoa powder, flour, baking soda, baking powder, and salt. In a separate bowl, whisk oil, vanilla, eggs, and buttermilk.
Pour the dry ingredients into the wet, whisking until no lumps remain. Pour in brewed coffee, mixing until just combined.
Use 1/3 cup measuring cup or a large ice cream scoop to divide the batter evenly between the cupcake liners, filling them about 2/3 of the way. Bake for roughly 25 minutes, or until a knife inserted in the center of the cupcake comes out clean. Cool completely on a wire rack before frosting.
To make the frosting, place butter and cream cheese in a standing mixer fitted with a paddle attachment (an electric hand mixer also works). Cream on high speed for 1 minute, then turn speed to low and add in cocoa powder. Mix until combined, then add in powdered sugar, brewed coffee, vanilla extract, and salt. Cream on high speed for 1 minute, until mixture has lightened slightly and is fluffy.
Transfer the frosting to a piping bag fit with desired tip and frost the cooled cupcakes!