Pineapple Cupcakes: Add all cake ingredients into the bowl of a stand mixer or use a mixing bowl and hand mixer.

Line a cupcake/muffin pan with paper liners. Using a 1 tablespoon cookie scoop, add three scoops of batter to each cup.

Bake the cupcakes at 325 degrees for 13-18 minutes until a toothpick inserted comes out clean.

Pineapple Filling: Add crushed pineapple, sugar, and corn starch to a saucepan. Cook over medium heat, stirring constantly, until boiling. Reduce the heat and simmer, while continuing to stir, for 5 minutes. Remove the pineapple filling from the heat, stir in the butter and allow to cool. Reserve ¼ cup of filling to make the frosting.

Pineapple Buttercream: Place the softened butter in the bowl of a stand mixer with the paddle attachment. Whip the butter until light and fluffy.

Mix in vanilla, Jello mix, and reserved pineapple filling. Then add the powdered sugar 1 cup at a time, mixing in between.

Add the milk, one tablespoon at a time, until the desired consistency is reached.

Cupcake Assembly: Use a cupcake corer or a knife to remove the center of each cupcake.

Add the filling to a piping bag with the end snipped off. Pipe the filling into the middle of each cupcake.

Add the frosting to piping bag with a large star tip. Pipe the buttercream on top of the cupcakes in a circular motion to mimic a Dole Whip.