To fill the cupcakes, cut a small core from the center of each one using a knife or cupcake corer.
Pipe or spoon the filling into the hollow centers, then replace the top part of the removed cake. You can trim down the piece before replacing it, as you won’t need the entire core with the filling inside.
To prepare the chocolate ganache topping, place the chocolate chips into a medium-sized heatproof bowl.
Heat the heavy cream just until it starts to boil, then pour it over the chocolate chips. Let it sit for 2 to 3 minutes, then whisk until the mixture is smooth and glossy.
Spread the ganache over the top of each cupcake, covering it completely. If the ganache thickens too much as it cools, you can reheat it briefly—5 to 10 seconds in the microwave should make it spreadable again.
To make the decorative vanilla icing, beat the butter in a mixer bowl until smooth.
Add the powdered sugar and mix until it begins to come together—it may be a bit dry and clumpy at first.
Add in the milk and a splash of vanilla extract, then mix until the icing becomes smooth and pipeable.
Transfer the icing to a piping bag fitted with a small round tip (such as Wilton tip #3) and pipe the classic swirl design across the top of each cupcake.
Keep the cupcakes refrigerated until you’re ready to serve. For the best texture and flavor, let them sit at room temperature for a bit before enjoying. Serve cool, but not cold.