Preheat oven to 350 degrees. Line two 12-cup cupcake pans with cupcake liners and set aside.

In a medium mixing bowl, sift together cake mix and pudding and set aside. In the bowl of a stand mixer (or large mixing bowl) using the paddle attachment, beat together eggs, sour cream, and milk at low speed. Add dry ingredients and beat until just combined. Beat in melted butter until just combined. Once all ingredients are incorporated, scrape the sides and bottom of the bowl and turn mixer up to medium and beat once more for 15–20 seconds. Do not overbeat.

Spoon three tablespoons of batter into each cupcake liner and bake on middle oven rack for 16–18 minutes, baking up to 24 cupcakes side by side at a time. (For best results, bake cupcakes one pan at a time.) Once a toothpick comes out clean, remove from oven and allow cupcakes to rest in pan for 2–4 minutes before removing and transferring to a cooling rack. Prepare pan and repeat this step with any remaining batter.

While cupcakes are cooling, prepare frosting and topping. In a small bowl, combine chocolate malt powder and four tablespoons of milk and set aside. In the bowl of a stand mixer (or large mixing bowl) using the paddle attachment, cream butter at medium speed until soft and smooth. Add shortening and vanilla extract and beat until combined. Slowly add in powdered sugar, beating slightly between each addition. Pour in dissolved chocolate malt and beat until combined. Add milk one tablespoon at a time, beating in between additions until at desired consistency. Turn mixer up to medium-high and beat for 1–2 minutes.

To prepare whipped topping, chill a large metal mixing bowl and whisk attachment. Once cold, beat heavy whipping cream on medium-high until stiff peaks have formed. Beat in powdered sugar.

Once cupcakes have completely cooled, pipe chocolate malt buttercream and whipping cream using the two-layer effect. Keep refrigerated, and top with cherries just before serving.