Rich and moist chocolate cupcakes topped with decadent chocolate buttercream.
Preheat the oven to 325˚F and line a muffin pan with cupcake liners. Sift together the flour, cocoa powder, baking powder, baking soda, and salt. Place the sifted dry ingredients into the bowl of your stand mixer fitted with the paddle attachment. Add the sugar to the mixture and mix at low speed until blended. Add the vegetable oil and continue to mix until the mixture is crumbly, about 1 minute.
In a separate medium-sized bowl, whisk together the eggs, milk and vanilla extract until blended. With the mixer at low speed, add the egg mixture to the flour mixture and mix for two minutes, scraping down the bowl and paddle as necessary.
Slowly add the boiling water and mix until just blended and the batter is smooth, scraping down the bowl and paddle to ensure uniform consistency. Pour the batter evenly amongst cupcake liners, about ⅔ full each. Bake the cupcakes for 17 minutes, or until a toothpick inserted comes out clean. Let cool thoroughly before frosting.
In a stand mixer fitted with a paddle attachment, whip butter on medium speed until creamy and light in color, about four minutes. Scrape down the bowl and paddle and turn the mixer to low, then add powdered sugar, cocoa powder, milk, salt, and vanilla extract. Increase the speed to high and beat for three minutes.
Let the cupcakes cool thoroughly before frosting with chocolate buttercream. In the images above, I've used Wilton tip 1M to pipe a swirl with the buttercream before adding sprinkles.
Make Ahead Tips: The cupcakes can be made ahead and stored at room temperature, covered with plastic wrap, for up to two days. Alternatively, they can be stored in an airtight container in the freezer for up to two months.
The buttercream recipe can be made ahead and stored in an airtight container in the refrigerator for up to two weeks. When you’re ready to use it, re-whip with your stand mixer.