Preheat your oven to 350ºF and line your cupcake tray with paper liners to make cleanup a breeze and ensure your cupcakes come out perfectly shaped.
Crush your Nilla Wafers into fine crumbs using a food processor, or seal them in a zip-top bag and gently crush with a rolling pin.
In a large bowl, combine the Nilla wafer crumbs, cake flour, baking powder, and salt. Whisk everything together to create the light and soft base for your cupcakes.
Beat the melted butter and brown sugar in a separate bowl until the texture is silky and just a bit airy. This gives your cupcakes that rich, caramel-like flavor.
Add the egg, mashed banana, and vanilla to the butter-sugar mixture. Whip it all together until you achieve a smooth, cohesive consistency.
Add the dry mixture to the wet ingredients a little at a time, stirring softly until the batter becomes thick and smooth.
Stir the milk into the mixture until the batter becomes silky and well incorporated.
Scoop about ¼ cup of the batter into each cupcake liner, filling them halfway.
Bake for 20 minutes, or until the tops are golden and spring back when touched. Let them cool on a wire rack.
As the cupcakes cool, mix the instant pudding with cold milk to prepare the banana pudding filling.
Let it thicken for a few minutes, then gently fold in the chopped banana pieces. Now your creamy pudding is ready!
Whisk the powdered sugar and cornstarch in a small saucepan to prepare the foundation for your frosting.
Whisk in ½ cup of heavy cream until the mixture is cohesive, then cook over medium heat, stirring nonstop, until it reaches a thick, pudding-like texture.
Take the mixture off the heat and allow it to cool to room temperature.
Beat the leftover heavy cream and vanilla extract with a mixer until soft, fluffy peaks develop.
Add the thickened cream bit by bit, whipping until the mixture forms stiff, stable peaks. You’ll have the perfect frosting for piping.
Now it’s time to assemble! Use a small pairing knife to carve out a hole in the center of each cooled cupcake, making a little pocket. Fill the hole with the banana pudding mixture.
Pipe the whipped cream frosting generously on top of each cupcake, creating a fluffy swirl of sweetness.
Complete each cupcake by placing a Nilla Wafer on top. This adds that perfect crunch and flavor to tie everything together. Enjoy!