Preheat the oven to 350°F (175°C) and line a muffin pan with 24 cupcake liners.

Cream together 1 cup of softened unsalted butter and 1.5 cups of granulated sugar until light and fluffy.

Add 3 large eggs, 1 cup of milk, and 0.5 cup of pineapple juice, mixing until combined.

In a separate bowl, whisk 2.5 cups of flour, 2 teaspoons of baking powder, 0.5 teaspoon of baking soda, and 0.25 teaspoon of salt.

Gradually combine dry ingredients into the wet mixture, then fold in 1 cup of crushed pineapple.

Fill cupcake liners about ⅔ full and bake for 14-16 minutes or until a toothpick comes out clean.

Let the cupcakes cool completely before filling them.

In a saucepan, combine 1 cup of crushed pineapple, 3 tablespoons of corn starch, and 0.25 cup of sugar.

Cook over medium heat, stirring until the mixture thickens and comes to a gentle boil for about 1 minute.

Remove from heat and chill in the fridge until firm.

Beat 1 cup of softened unsalted butter with 0.25 cup of pineapple juice and 2 teaspoons of vanilla extract.

Gradually mix in 4 cups of confectioners' sugar, adjusting with milk if necessary until fluffy.

Create a hollow in the center of each cooled cupcake and fill with chilled pineapple filling.

Top with the creamy Dole Whip frosting, swirling it on for a beautiful finish.