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Pineapple upside down cupcakes 2026 01 08 173723 683x1024

Pineapple Upside-Down Cupcakes

Delightful cupcakes featuring a moist vanilla base topped with pineapple chunks and cherries, reminiscent of the classic pineapple upside-down cake.
Prep Time 15 minutes
Cook Time 25 minutes
Total Time 40 minutes
Course Dessert, Snack
Cuisine American
Servings 12 cupcakes
Calories 220 kcal

Ingredients
  

Toppings

  • 6 tablespoons melted butter
  • ¾ cup brown sugar
  • 1 can 20-ounce can of pineapple chunks in pineapple juice (or fresh chopped pineapple)
  • 12 pieces maraschino cherries

Cupcake Batter

  • ½ cup softened unsalted butter Make sure it's at room temperature.
  • ¾ cup granulated sugar
  • 2 pieces eggs
  • 1 teaspoon vanilla extract
  • 1 ½ cups all-purpose flour
  • 1 ½ teaspoons baking powder
  • ¼ teaspoon salt
  • ½ cup buttermilk Can substitute with regular milk mixed with vinegar or lemon juice.

Instructions
 

Toppings

  • Preheat your oven to 350°F (175°C) and line a cupcake pan with cupcake liners.
  • In a small bowl, melt the 6 tablespoons of butter and mix in the brown sugar. Divide this mixture evenly among the bottom of each cupcake liner.
  • Place a few pineapple chunks and a maraschino cherry on top of the brown sugar mixture in each liner.

Cupcake Batter

  • In a large mixing bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy.
  • Beat in the eggs, one at a time, and then add the vanilla extract.
  • In another bowl, mix the all-purpose flour, baking powder, and salt.
  • Gradually add the dry ingredients to the butter mixture, alternating with the buttermilk. Mix until just combined.
  • Spoon the batter over the pineapple topping in each cupcake liner, filling about 2/3 full.
  • Bake for 20-25 minutes or until a toothpick comes out clean from the center.
  • Allow the cupcakes to cool for a few minutes, then carefully turn them upside down onto a serving platter.

Notes

Serve warm or at room temperature. These cupcakes can be topped with whipped cream or vanilla ice cream. Store leftover cupcakes in an airtight container at room temperature for up to two days, or refrigerate for up to a week.
Keyword Cupcakes, Easy Baking, Pineapple dessert, Pineapple Upside-Down Cupcakes, Tropical cupcakes