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Pineapple Upside Down Cupcakes Recipe

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3.9 from 13 reviews

These Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, combining moist, buttery cake with a caramelized pineapple and cherry topping. Perfect for parties or a sweet treat, they bake up individually in a muffin pan, making them easy to serve and enjoy.

  • Total Time: 37 minutes
  • Yield: 21 cupcakes

Ingredients

Topping

  • ½ cup butter, melted
  • ½ cup brown sugar, packed
  • 1 can (20 ounces) pineapple slices or chunks with juice, divided
  • 21 maraschino cherries, stemless

Cake Batter

  • 2 cups all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
  • ½ teaspoon baking soda
  • ¼ cup canola oil
  • ¾ cup granulated sugar
  • 2 large eggs, room temperature

Instructions

  1. Preheat Oven: Preheat your oven to 350°F (177°C) to get it ready for baking the cupcakes.
  2. Prepare Pineapple: Separate the pineapple slices or chunks from their juice. Cut the pineapple into small pieces about ½ inch square for easy layering in the cupcake tins.
  3. Prepare Muffin Pan: Spoon 1 teaspoon of melted butter into each muffin cup. Sprinkle about 1 teaspoon of brown sugar over the butter to create the caramelized topping base.
  4. Arrange Toppings: Place 4 pineapple pieces per cup in a flower or cross pattern. Then, place one maraschino cherry in the center of each pineapple arrangement. Set the pan aside once complete.
  5. Mix Dry Ingredients: In a small bowl, whisk together the all-purpose flour, baking powder, salt, and baking soda to evenly distribute the leavening agents.
  6. Combine Wet Ingredients: In a large mixing bowl, whisk the canola oil and granulated sugar together. Then beat in the eggs one at a time until just combined, creating a smooth mixture.
  7. Combine Wet and Dry: Add the dry ingredients to the wet mixture and mix gently with a spatula. When the batter starts to become thick and dry, gradually pour in the reserved pineapple juice while continuing to mix until the batter is wet and thick but smooth.
  8. Fill Muffin Cups: Spoon about 2 tablespoons of the batter over the pineapple and cherry toppings in each muffin cup, filling nearly to the top.
  9. Bake: Place the pan in the preheated oven and bake for 15-17 minutes, or until the cupcake edges are golden brown and a toothpick inserted in the center comes out clean. Note that some butter may seep out during baking.
  10. Cool: Allow the cupcakes to cool in the pan for 30 minutes to set up and prevent breaking.
  11. Remove from Pan: Run a thin, small knife around the edges of each cupcake to loosen it gently from the pan.
  12. Invert and Serve: Carefully flip each cupcake upside-down onto a cooling rack, showcasing the caramelized pineapple and cherry topping. Let cool completely before serving.

Notes

  • Using room temperature eggs helps achieve a smoother batter.
  • Make sure to grease the muffin pan well to easily release the cupcakes upside-down.
  • You can use pineapple chunks if slices are not available—just cut them smaller.
  • Store leftover cupcakes in an airtight container at room temperature for up to 3 days.
  • For a variation, try adding a pinch of cinnamon to the batter for warmth.
  • Author: Daisy
  • Prep Time: 15 minutes
  • Cook Time: 17 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American