Preheat your oven to 350°F (175°C) and line a cupcake pan with paper liners.
In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract.
In a separate bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry mixture to the wet mixture, alternating with the milk, starting and ending with the dry ingredients.
Fold in the crushed pineapple gently until just combined.
Divide the batter evenly among the prepared cupcake liners, filling each about two-thirds full.
Bake for 18-20 minutes, or until a toothpick inserted in the center comes out clean.
Allow the cupcakes to cool in the pan for 5 minutes before transferring them to a wire rack to cool completely.
For the frosting, beat the heavy cream with powdered sugar until stiff peaks form.
Gently fold in crushed pineapple, ensuring it's well-distributed throughout the frosting.
Frost the cooled cupcakes with the pineapple frosting and top with a maraschino cherry, if desired.