Description

These pineapple upside-down cupcakes are a delightful twist on the classic pineapple upside-down cake, perfect for serving at parties, potlucks, or just as a sweet treat for yourself. With a base of buttery, caramelized pineapple and cherries, and a soft, moist cake on top, these single-serving desserts are both delicious and visually appealing. The cupcakes offer all the tropical flavors of the traditional dessert in a convenient, handheld form.

Ingredients

Scale

For the Topping:

½ cup melted butter
1½ cups brown sugar
24 maraschino cherries
1 (20 oz) can crushed pineapple, well-drained

For the Cake:

1 (18.25 oz) package pineapple cake mix (e.g., Duncan Hines® Pineapple Supreme)
1⅓ cups pineapple juice (reserved from the canned pineapple)
3 large eggs
⅓ cup vegetable oil

For Finishing (Optional):

1 tbsp confectioners’ sugar, for dusting

Instructions

Preheat the oven to 350°F (175°C).
Spray 24 muffin cups with non-stick cooking spray to prevent sticking.
Prepare the topping:
Add 1 teaspoon of melted butter into each muffin cup. Sprinkle 1 tablespoon of brown sugar into each cup, then press a maraschino cherry into the center. Spoon a heaping tablespoon of well-drained crushed pineapple over the cherry and brown sugar, pressing gently to create an even layer.
Mix the cake batter:
In a large mixing bowl, combine the pineapple cake mix, reserved pineapple juice, eggs, and vegetable oil. Mix on low speed for 30 seconds to moisten the ingredients, then increase to medium speed and beat for 2 minutes until smooth.
Fill the muffin cups:
Pour the cake batter into the prepared muffin cups, filling each about two-thirds full to allow room for the cupcakes to rise.
Bake:
Bake in the preheated oven for about 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. Avoid overbaking to ensure the cupcakes remain moist.
Cool and invert:
Allow the cupcakes to cool in the pan for 5 minutes. Run a knife around the edges of each cupcake to loosen them, then carefully invert the muffin tin onto a baking sheet lined with wax paper.
Optional finishing touch:
Dust the tops of the cupcakes with confectioners’ sugar for a sweet, decorative touch before serving.

Notes

Pineapple juice: Be sure to use the juice reserved from the canned pineapple for extra flavor in the cake batter.
Draining the pineapple: Make sure the crushed pineapple is well-drained to prevent the cupcakes from becoming soggy.
Storing: These cupcakes can be stored in an airtight container in the refrigerator for up to 3 days. Reheat in the microwave for 10-15 seconds for a warm treat.
Variations: Feel free to experiment by adding coconut to the batter or topping, or by using different fruits like peaches or mango for a unique twist on the classic recipe.