To get started, preheat your oven to 350°F. Next, either coat the 12-cup muffin pan with cooking spray or line it with paper liners.
In a stand mixer bowl or a large mixing bowl, whisk together sugar, flour, cocoa, baking powder, baking soda, and salt. Incorporate the egg, milk, oil, and vanilla, and beat on medium speed for approximately 2 minutes. Finally, blend in the boiling water. The batter should have a thin consistency. Evenly distribute it among the pan wells, ensuring they are no more than 3/4 full.
After baking for 15-18 minutes, or until a toothpick inserted in the center comes out clean, allow the cupcakes to cool in the tin for 5 minutes. Then, transfer them to a cooling rack to cool completely.
While you're at it, transfer the cream to a clean, spacious mixing bowl or the stand mixer bowl with the whisk attachment. Whip the cream vigorously until soft peaks emerge, which usually takes about 3 minutes. Then, incorporate sugar, vanilla, and kirsch if you choose, and continue to whip until you achieve stiff peaks in 2-3 more minutes. Store the whipped cream in the fridge for cupcake assembly.
Once the cupcakes have cooled, take a paring knife and carefully cut a 1 1/2-inch diameter cone from the top of each cupcake, making sure not to cut through the bottom. Then, fill the center of each cupcake with cherry pie filling.
Use a pastry bag with a round tip to transfer the whipped cream onto the cupcakes. Finish by topping each cupcake with a fresh cherry and chocolate shavings.