Preheat Oven and Line Pan:

Heat the oven to 350°F (175°C). Insert 24 paper liners into the muffin pan.

Mix Batter with Pineapple:

In a stand mixer or a large bowl using a hand mixer, beat together the butter and sugar until creamy. Incorporate the eggs, milk, and pineapple juice, blending thoroughly. Sift or whisk the flour, baking powder, baking soda, and salt to remove lumps. Add these dry components to the wet mixture. Fold in the crushed pineapple.

Fill Liners and Bake:

Spoon about 3 tablespoons of batter into each liner, filling them two-thirds full. Bake for 14-16 minutes until the tops bounce back when pressed lightly or a toothpick inserted in the center emerges clean. Let the cupcakes cool completely.

Cook Pineapple Filling:

While the cupcakes are baking, combine all pineapple filling items in a saucepan. Boil for 1 minute, then take off the heat. Refrigerate the filling until chilled.

Make Dole Whip Frosting:

In a stand mixer or a large bowl with a hand mixer, mix together the pineapple juice, butter, and vanilla. Gradually incorporate the confectioners' sugar until smooth. If the mixture is too thin, add more sugar; if too thick, add 1 tablespoon of milk.

Tint Frosting Yellow:

Add a few drops of yellow food coloring or icing gel to achieve a pale pastel yellow.

Fill Cupcakes with Filling:

Fill the cooled cupcakes with the pineapple filling by either carving a small hole in the top or using a piping bag fitted with a filling tip.

Pipe Frosting and Add Topper:

Finish by piping a swirl of Dole Whip frosting onto each cupcake and adding a leaf topper.