Preheat your oven to 350°F and line a cupcake pan with paper liners.
In a mixing bowl, beat the butter and sugar together on medium-low for 2–3 minutes until smooth.
Add eggs, vanilla, and milk. Mix until fully combined. (It may look a bit lumpy.)
Add flour, baking powder, salt, and cocoa powder. Mix on low until a smooth batter forms.
Divide the batter into the liners, filling each about ⅔ full. Bake for 15 minutes, or until centers are set.
To make the frosting, beat butter, powdered sugar, and cocoa powder on low until incorporated. Increase to medium speed and beat for 2–3 minutes until fluffy. Set aside ¼ cup and tint it red.
Transfer both frostings to piping bags. Use a large round tip for the chocolate frosting. Pipe a big swirl onto each cooled cupcake and dip into chocolate sprinkles.
Arrange six candy corn pieces at the top of each cupcake for tail feathers. Pipe a small tear drop of chocolate frosting in the center for the face.
Add candy eyes, insert a candy corn (tip up) as the beak, and finish with a red frosting dot for the wattle.