Yield: 30+ cupcakes
For the cupcakes:
2½ cups all-purpose flour
1 tbsp. baking powder
½ tsp. salt
12 tbsp. unsalted butter, at room temperature
2½ cups sugar
1 cup plus 2 tbsp. buttermilk
1 1/3 cups mashed ripe banana
For the filling:
1 lb. strawberries, hulled and diced small
2 tbsp. confectioners' sugar
12 oz. crushed pineapple, drained
For the frosting:
1½ cups heavy cream, chilled
1/3 cup confectioners' sugar, sifted
½ tsp. vanilla extract
For the ganache:
8 oz. bittersweet chocolate, chopped
1 cup heavy cream
1 tbsp. light corn syrup
To make the cupcakes, preheat the oven to 350° F. Line cupcake pans with paper liners. In a medium bowl combine the flour, baking powder and salt; whisk together and set aside. In the bowl of a stand mixer fitted with the paddle attachment cream together the butter and sugar on medium-high speed until light and fluffy, about 2 minutes. Reduce the mixer speed to medium low and add in eggs one at a time, scraping down the sides of the bowl as needed. Mix in 1 the mashed banana until well combined. With the mixer on low speed alternately add the dry ingredients and buttermilk, beginning and ending with the dry ingredients and mixing only until just incorporated.
Divide the batter between the prepared cupcake liners, filling each about 2/3 to ¾ full. Bake until a toothpick inserted in the center comes out clean, about 20-22 minutes. Allow to cool in the pan 5-10 minutes, then transfer the cupcakes to a wire rack to cool completely.
To make the strawberry filling, combine the strawberries and confectioners' sugar in a medium bowl. Toss well, smashing slightly with a fork. Allow the berries to macerate at least 20-30 minutes.
To fill the cupcakes, cut a small cone out of the center of each cupcake with a paring knife or small biscuit cutter. (The excess cake can be discarded.) Add a teaspoon or two of the strawberry filling to the center of each cupcake. Top with a teaspoon or two of the crushed pineapple, filling to the top of the cupcake.
To make the frosting, add the heavy cream to the chilled bowl of an electric mixer fitted with a whisk attachment. Whip on medium-high speed until soft peaks form. Add the powdered sugar and continue to whip until thoroughly combined and stiff peaks form. Be careful not to over-beat! Blend in the vanilla extract.
Add the whipped cream to a pastry bag fitted with a large plain round tip. Pipe a swirl of the whipped cream onto each filled cupcake, covering the filling. Transfer the filled and frosted cupcakes to the refrigerator and chill for at least 30 minutes.
To make the ganache, place the chopped chocolate in a heatproof bowl. Bring the cream to a simmer over medium-high heat. Remove from the heat and pour the hot cream over the chocolate; let stand 1-2 minutes. Whisk together until a thick, smooth ganache forms. Blend in the corn syrup. Let stand at room temperature at least 10 minutes so the ganache is not hot.
To finish the cupcakes, pour a spoonful of the ganache over the whipped cream topping of each cupcake. Garnish with sprinkles and maraschino cherries before the glaze sets. Chill the assembled cupcakes until ready to serve.