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Pineapple Upside-Down Cupcakes Recipe

A nostalgic twist on a classic dessert, these Pineapple Upside-Down Cupcakes offer the delightful flavors of caramelized pineapple, sweet maraschino cherries, and a tender cake in a convenient, individual-sized treat. Perfect for any occasion, these cupcakes are as charming as they are delicious.
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Prep Time 20 minutes
Cook Time 20 minutes
Total Time 40 minutes
Course Dessert
Cuisine American
Servings 24 cupcakes
Calories 220 kcal

Ingredients
  

For the Topping:

  • 1/2 cup melted butter
  • 1 1/2 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)
  • 1 1/3 cups pineapple juice reserved from the canned pineapple
  • 3 large eggs
  • 1/3 cup vegetable oil

For Finishing:

  • 1 tbsp confectioners' sugar optional, for dusting

Instructions
 

  • Preheat your oven to 350°F (175°C).
  • Spray 24 muffin cups with cooking spray to prevent sticking.
  • Place 1 teaspoon of melted butter into each muffin cup.
  • Add 1 tablespoon of brown sugar to 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 mixture, pressing down gently to create an even layer.
  • 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 the batter is smooth and well-combined.
  • Pour the cake batter into the prepared muffin cups, filling each cup about 2/3 full to allow room for the cupcakes to rise.
  • Bake in the preheated oven for about 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
  • Be careful not to overbake to ensure the cupcakes stay moist.
  • Allow the cupcakes to cool in the pan for about 5 minutes. This helps the topping set slightly, making it easier to invert.
  • After cooling slightly, run a knife around the edges of each cupcake to loosen, then invert the muffin tin onto a baking sheet lined with wax paper.
  • For an extra touch of sweetness, lightly dust the tops of the cupcakes with confectioners' sugar before serving.

Notes

Customize these cupcakes with gluten-free or vegan ingredients as needed. You can also experiment with different toppings, such as using peach or pear slices instead of pineapple for a unique variation. Enjoy these sweet, nostalgic treats!

Nutrition

Serving: 80gCalories: 220kcal
Keyword caramelized, cupcakes, pineapple, sweet
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