Preheat the oven to 350°F (175°C) and line a cupcake pan with liners.
In a large mixing bowl, cream together the butter and sugar until light and fluffy.
Add in the eggs, one at a time, mixing thoroughly after each addition.
Mix in the vanilla extract.
In another bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture, alternating with the crushed pineapple.
Spoon the batter into the prepared cupcake liners, filling each about 2/3 full.
Bake in the preheated oven for 18-20 minutes or until a toothpick inserted into the center comes out clean.
Once baked, allow the cupcakes to cool in the pan for 5 minutes before transferring them to a wire rack.
In a mixing bowl, whip the heavy cream until stiff peaks form.
Gradually add the powdered sugar and pineapple extract, mixing until well combined.
Once the cupcakes are completely cool, frost them generously with the whipped pineapple cream.