Prepare the topping: Start by mixing the melted butter and brown sugar together in a small bowl. Spoon a little bit of this mixture into each cupcake cup, ensuring that the bottoms are evenly coated. This will create the rich, caramelized base that makes the upside-down effect so delicious. Place a pineapple slice or a few tidbits in the center of each cup, followed by a maraschino cherry if desired. The pineapple and cherry will be the stars of the show once the cupcakes are flipped over!
Make the cupcake batter: In a large mixing bowl, cream together the softened butter and sugar until light and fluffy. This should take about 3-4 minutes with an electric mixer. The mixture should turn pale and increase in volume. Add the eggs and vanilla extract, mixing until smooth and fully incorporated.
Stir in the pineapple juice or milk into the wet mixture. The pineapple juice will add a hint of tropical flavor and moisture to the cupcakes. If you prefer a milder flavor, you can substitute milk for the pineapple juice, but the juice will give the cupcakes a more authentic tropical taste.
Combine the dry ingredients: In a separate bowl, whisk together the flour, baking powder, and salt. Slowly add this dry mixture into the wet ingredients, mixing gently until just combined. Be careful not to overmix, as this can lead to dense cupcakes. The batter should be smooth and slightly thick.
Fill the cupcake cups: Scoop the batter evenly over the pineapple layer in each cupcake cup, filling each about ¾ full. This will leave room for the cupcakes to rise as they bake without overflowing. Smooth the tops of the batter to ensure an even bake.
Bake the cupcakes: Place the cupcake tray in a preheated oven at 170°C (350°F). Bake for 18–22 minutes, or until the tops of the cupcakes are golden and firm to the touch. You can test the doneness by inserting a toothpick into the center; it should come out clean when the cupcakes are ready.
