Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

24 servings
Pineapple Upside Down Cupcakes - a mini version of your favorite pineapple upside down cake with butter, brown sugar, pineapple, and a cherry on top! This easy recipe starts with a cake mix.

Ingredients

  • cooking spray
  • 1/2 cup butter

    melted

  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 1 can crushed pineapple

    20 ounce

  • 1 package yellow cake mix)

    15.25 ounce

  • 1 1/3 cups pineapple juice)

    (you just need as much pineapple juice as water called for on the cake mix package - see note

  • confectioners' sugar for dusting

Directions

  1. 1

    Preheat oven to 350 degrees and spray 24 muffin cups with cooking spray.

  2. 2

    Line a work surface with parchment or waxed paper.

  3. 3

    Spoon 1 teaspoon melted butter into the bottom of the pan of each sprayed muffin cup.

  4. 4

    Spoon 1 tablespoon brown sugar in each muffin cup.

  5. 5

    Press a maraschino cherry into the center of the brown sugar in each muffin cup.

  6. 6

    Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.

  7. 7

    Mix cake mix according to the package directions, substitute pineapple juice for the water in the recipe. This may vary according to which cake mixture you use. In large bowl with electric mixer on low speed until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.

  8. 8

    Pour pineapple cake batter into the muffin cups, filling them almost to the top.

  9. 9

    Bake in the preheated oven on the middle rack until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.

  10. 10

    Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper to release. Serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners' sugar if desired.

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

30 min24 servings

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About this Recipe

Craving the nostalgic comfort of pineapple upside-down cake, but in a perfectly portioned, easy-to-share format? These Pineapple Upside Down Cupcakes deliver all the classic flavors you love, transforming a beloved dessert into a delightful, individual treat ready in about 30 minutes.

This recipe shines by taking the traditional upside-down cake elements—rich butter, sweet brown sugar, tangy pineapple, and a bright maraschino cherry—and miniaturizing them with remarkable ease. Starting with a yellow cake mix simplifies the baking process, ensuring a consistently moist crumb while still giving you that homemade taste everyone adores.

Expect a moist, tender cupcake crowned with a beautifully caramelized, sticky-sweet topping. Each bite offers a harmonious blend of buttery brown sugar, the vibrant acidity of crushed pineapple, and the signature pop of a maraschino cherry. The pineapple juice incorporated into the cake mix ensures a cohesive tropical flavor throughout, making this an irresistible dessert that feels both fancy and approachable. It's a surprisingly straightforward recipe that yields impressive results, perfect for bakers of any skill level.

While these cupcakes perfectly capture the beloved classic, you can customize them slightly. Feel free to arrange the crushed pineapple to your preference, creating a denser fruit layer if desired, or even adding an extra maraschino cherry for a bolder splash of color and sweetness. The versatility of the yellow cake mix means you can easily achieve your desired cake texture by choosing your favorite brand.

Serve these delightful cupcakes as a charming dessert for parties, potlucks, or simply as a sweet treat to brighten any day. A light dusting of confectioners' sugar adds an elegant finishing touch, enhancing their visual appeal.

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