Preheat your oven to 350°F.
In a mixing bowl, whisk together the all-purpose flour, granulated sugar, cocoa powder, baking powder, baking soda, and salt.
Incorporate the egg, milk, vegetable oil, and vanilla extract into the dry ingredients. Blend until thoroughly combined.
Carefully stir in the boiling water. The batter will be thin.
Line a 12-cup muffin tin with cupcake liners. Fill each cupcake liner about 2/3 full with the batter.
Bake in the preheated oven for 18 to 20 minutes, or until a toothpick inserted into the center comes out clean.
Remove cupcakes from the oven, cool in the pan for 5 minutes, then transfer to a wire rack to cool completely.
In a large bowl, beat the cold heavy whipping cream and powdered sugar until stiff peaks form.
Take a small knife or cupcake corer to hollow out the center of each cooled cupcake. Next, spoon cherry pie filling into each hollowed center.
Pipe or spoon the whipped cream over each filled cupcake.
Sprinkle chocolate shavings over the whipped cream.