Preheat oven to 325 degrees and line a muffin tin with cupcake liners. Sift flour, baking powder, baking soda, salt and cocoa powder into a large mixing bowl. Add sugar and stir to combine.

Add oil, milk, beaten egg and vanilla to dry ingredients and whisk until completely combined. Carefully stir in boiling water, scraping the sides of bowl until everything is combined. The batter will be thin.

Fill baking cups about ¾ full and bake for 14–16 minutes or until tops are firm and a cake tester comes out clean. Remove cupcakes from oven and cool completely. While cupcakes are cooling, fill a piping bag fitted with a large star tip with whipped topping or whipped cream and refrigerate until ready to use.

When cupcakes are cooled, scoop out a 1" diameter divot in the center of the top of each cupcake. Just make an indentation deep enough to hold about 1 Tbsp of filling. You can use the crumbs from the scooped-out cake to garnish the cupcakes or consider it the chef’s treat.

Pipe a ring of whipped cream around the edge of each cupcake right between the outer edge of the cupcake and the divot in the middle. Spoon enough cherry pie filling into the center of each cupcake to fill just above the level of the icing. Sprinkle with shaved chocolate or reserved cake crumbs and serve or refrigerate until ready to serve.