Prepare the Oven and Pan: Preheat the oven to 350°F and line a cupcake pan with cupcake liners. Set the prepared pan aside.
Combine the Dry Ingredients: In a medium bowl, whisk together the flour, cocoa powder, baking soda, baking powder, and salt until evenly combined.
Blend the Sugar and Oil: Using a stand mixer fitted with the paddle attachment, mix the granulated sugar and vegetable or canola oil for 1 minute, or until well combined.
Add the Wet Ingredients: Add the vanilla extract, eggs, milk, orange zest, and orange juice to the sugar-and-oil mixture. Mix until the ingredients are fully combined.
Finish the Cupcake Batter: Add the dry ingredient mixture to the wet ingredients and mix only until everything has just come together. Do not overmix the batter.
Fill the Cupcake Liners: Portion the batter into the lined cupcake pan, filling each liner about halfway. A large size 20, 3-tablespoon cookie scoop can be used for consistent portions.
Bake the Cupcakes: Bake at 350°F for 12–15 minutes, or until a toothpick inserted into a cupcake comes out with a few moist crumbs. The original recipe baked in about 13 minutes, so avoid overbaking, which can make the cupcakes dry.
Cool the Cupcakes: Remove the pan from the oven and let the cupcakes rest in the pan for 5 minutes. Transfer them to a wire rack and allow them to cool completely before frosting.
Beat the Butter: Place the slightly cold, room-temperature unsalted butter in the stand mixer bowl and beat on medium speed for 1–2 minutes, until smooth.
Build the Buttercream: Add the cocoa powder and powdered sugar gradually, adding the powdered sugar ½ cup at a time and mixing until smooth after each addition.
Add the Orange Flavor: Mix in the vanilla extract, orange juice, and orange zest until the buttercream is smooth and well combined.
Adjust the Consistency: Add a little more orange juice or milk as needed to reach the desired frosting consistency. If the buttercream becomes too thin, add a small amount of additional powdered sugar.
Pipe the Frosting: Transfer the finished buttercream to a piping bag and pipe it onto the completely cooled cupcakes.
Garnish the Cupcakes: If desired, finish each cupcake with a fresh orange slice.