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Moist pineapple upside-down cupcakes with caramelized pineapple and maraschino cherries on top.

Pineapple Upside-Down Cupcakes Recipe


  • Author: Ava
  • Total Time: 40 minutes
  • Yield: 12 cupcakes 1x

Description

These pineapple upside-down cupcakes are the perfect bite-sized version of the classic cake. Made with sweet caramelized pineapple, brown sugar, and a moist vanilla cake, they’re easy to bake and absolutely delicious. Perfect for parties, holidays, or a simple dessert at home.


Ingredients

Scale
For the Topping:
  • ¼ cup unsalted butter (melted)
  • ½ cup brown sugar
  • 1 can (20 oz) pineapple slices (cut into chunks)
  • 12 maraschino cherries
For the Cupcakes:
  • 1 ½ cups all-purpose flour
  • ¾ cup granulated sugar
  • 1 ½ tsp baking powder
  • ½ tsp salt
  • ½ cup unsalted butter (softened)
  • 2 large eggs
  • ½ cup pineapple juice (reserved from canned pineapple)
  • 1 tsp vanilla extract

Instructions

  • Preheat oven to 350°F (175°C) and grease a 12-cup muffin tin.
  • Make the topping: Divide melted butter evenly into the muffin cups, sprinkle brown sugar, place pineapple chunks, and add a cherry in the center.
  • Prepare the batter: In a large bowl, whisk together flour, sugar, baking powder, and salt. Add butter, eggs, pineapple juice, and vanilla extract. Mix until smooth.
  • Fill the muffin cups: Spoon batter over the pineapple topping, filling each cup ¾ full.
  • Bake for 20-25 minutes, or until a toothpick inserted in the center comes out clean.
  • Cool & flip: Let cupcakes rest for 5 minutes, then place a tray over the tin and carefully flip them over.
  • Serve warm or at room temperature.

Notes

  • Grease the muffin tin well to prevent sticking.
  • For extra moisture, brush the baked cupcakes with pineapple juice.
  • Let them cool slightly before flipping to keep the topping intact.
  • Prep Time: 15 minutes
  • Cook Time: 25 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Calories: 220 kcal
  • Sugar: 22g
  • Sodium: 120mg
  • Fat: 9g
  • Saturated Fat: 5g
  • Carbohydrates: 32g
  • Protein: 2g
  • Cholesterol: 45mg

Keywords: Mini pineapple upside-down cakes, pineapple cupcakes, caramelized pineapple cupcakes, pineapple cherry cupcakes