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The Best Pineapple Upside Down Cupcakes Recipe

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3.9 from 9 reviews

These Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, combining moist yellow cake with caramelized brown sugar, maraschino cherries, and juicy pineapple pieces on top. Perfectly portioned as individual cupcakes, they offer a burst of tropical flavor with every bite and are easy to make by substituting pineapple juice for water in the cake mix for enhanced moisture and taste.

  • Total Time: 30 minutes
  • Yield: 24 servings

Ingredients

For the Topping

  • 1/2 cup butter, melted
  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 1 (20 ounce) can crushed pineapple or pineapple tidbits, well drained (reserve juice)

For the Cake Batter

  • 1 (15.25 ounce) package yellow cake mix (plus ingredients called for on the package except water)
  • 1 cup pineapple juice (to substitute water called for on the cake mix package)

For Garnish

  • Powdered sugar for dusting (optional)

Instructions

  1. Preheat Oven and Prepare Pan: Preheat your oven to 350°F (175°C) and line 24 muffin cups with baking cups to ensure easy removal and clean baking.
  2. Prepare Topping Base: Spoon 1 teaspoon of melted butter into the bottom of each muffin cup, then add 1 tablespoon of brown sugar on top of the butter in each cup to create the caramelized topping layer.
  3. Add Cherries and Pineapple: Press a maraschino cherry into the center of the brown sugar in each muffin cup. Then, evenly distribute about 1 tablespoon of well-drained crushed pineapple or approximately 5 pineapple tidbits over each cherry to form the classic upside-down topping.
  4. Mix Cake Batter: Prepare the yellow cake mix as per package directions, substituting the water with the reserved pineapple juice. Using an electric mixer, blend on low speed for about 30 seconds until moistened; then increase to medium speed and mix for 2 minutes until smooth.
  5. Fill Muffin Cups: Spoon the pineapple cake batter into each prepared muffin cup, filling them approximately three-quarters full to allow room for rising.
  6. Bake: Place the muffin tins on the middle rack of the preheated oven and bake for about 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
  7. Cool and Invert: Allow the cupcakes to cool in the pan for about 20 minutes. Carefully unwrap the cupcakes and invert them onto a serving platter so the pineapple, cherry, and sugar topping are on top.
  8. Serve: Dust lightly with powdered sugar if desired, and serve warm or at room temperature for the best flavor and texture.

Notes

  • Be sure to drain the pineapple well to prevent excess moisture which can make the topping soggy.
  • Using pineapple juice instead of water enhances the pineapple flavor throughout the cake.
  • You can substitute maraschino cherries with fresh cherries if desired, but the classic color and flavor come from maraschino cherries.
  • Allow cupcakes to cool slightly before inverting to prevent the topping from sticking.
  • Author: Daisy
  • Prep Time: 10 minutes
  • Cook Time: 20 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Find it online: https://dishiary.com/the-best-pineapple-upside-down-cupcakes-recipe/