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Pineapple Upside Down Cupcakes Recipe

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4.2 from 72 reviews

These Pineapple Upside Down Cupcakes are an individual twist on the classic dessert, featuring moist yellow cake topped with caramelized brown sugar, juicy pineapple pieces, and sweet maraschino cherries. Perfect for parties or a delightful treat, they offer a combination of tangy and sweet flavors with a beautiful presentation.

  • Total Time: 40 minutes
  • Yield: 24 cupcakes

Ingredients

Pineapple Topping

  • 1 (20-ounce) can pineapple rings, drained and juice reserved
  • ⅔ cup brown sugar, packed
  • ⅓ cup butter, melted
  • 12 maraschino cherries, cut in half

Cake Batter

  • 1 (15.25-ounce) box yellow cake mix
  • ½ cup vegetable oil
  • 3 eggs
  • Reserved pineapple juice from the can

Instructions

  1. Preheat Oven and Prepare Muffin Tin: Preheat your oven to 350°F (175°C). Spray the wells of a 24-cup muffin tin with cooking spray to prevent sticking and for easy removal of cupcakes.
  2. Prepare Cake Batter: In a large bowl, combine the reserved pineapple juice, yellow cake mix, vegetable oil, and eggs. Mix until all ingredients are well blended and smooth, ensuring an even and moist batter.
  3. Prepare Pineapple Topping: Cut each pineapple ring into four equal pieces. In a separate bowl, mix the melted butter and brown sugar until combined. Add about 1 teaspoon of this butter and brown sugar mixture into the bottom of each muffin well.
  4. Assemble Cupcakes: Place two pineapple pieces in each muffin well over the butter-sugar mixture. Add one half of a maraschino cherry on top of the pineapple pieces, cut side facing upward for an attractive look.
  5. Add Cake Batter: Pour the prepared cake batter into each muffin well, filling to about ¼ inch from the top to allow room for rising during baking.
  6. Bake: Bake the cupcakes in the preheated oven for 20-25 minutes or until the tops are golden brown and a toothpick inserted in the center comes out clean.
  7. Cool and Invert: Remove the cupcakes from the oven and let them cool in the muffin tin for 15 minutes. Then, gently loosen the sides of each cupcake with a knife and carefully invert the muffin tin onto a cooling rack to release the cupcakes, revealing the pineapple and cherry topping.
  8. Serve: Serve these delicious Pineapple Upside Down Cupcakes warm, optionally topped with freshly whipped cream for added indulgence.

Notes

  • Use fresh pineapple juice from the can for optimal flavor and moisture in the cake batter.
  • Make sure to spray the muffin tin wells thoroughly to ensure easy removal of cupcakes.
  • Letting the cupcakes cool for 15 minutes before inverting helps the topping set and prevents breaking.
  • These cupcakes are best enjoyed warm but can be served at room temperature as well.
  • Store leftovers in an airtight container at room temperature for up to 2 days or refrigerate for up to 4 days.
  • Reheat gently before serving to enjoy the soft texture and warm topping.
  • Author: Adeline
  • Prep Time: 15 minutes
  • Cook Time: 20-25 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American