01 - Preheat oven to 350°F (175°C). Line a standard muffin tin with 12 cupcake liners.
02 - In a medium mixing bowl, whisk together all-purpose flour, baking powder, and salt until thoroughly blended.
03 - In a large mixing bowl, cream softened butter and granulated sugar with an electric mixer until light and fluffy. Add eggs individually, beating after each addition.
04 - Stir in crushed pineapple, pineapple juice, whole milk, and vanilla extract until mixture is evenly combined.
05 - Gently fold dry ingredients into the wet mixture, stirring just until no streaks remain. Do not overmix.
06 - Evenly distribute the batter among cupcake liners. Bake for 16 to 18 minutes, or until a toothpick inserted in the center emerges clean.
07 - Allow cupcakes to cool in the pan for 5 minutes, then transfer to a wire rack until fully cooled.
08 - For the frosting, beat softened butter and cream cheese together until smooth. Gradually add sifted powdered sugar, mixing on low speed to combine. Incorporate pineapple juice, vanilla, and food coloring if using. Whip on high speed until light and fluffy.
09 - Once cupcakes are completely cooled, frost generously with pineapple whip frosting. Decorate with dried pineapple or maraschino cherries if desired.