Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes

Origin and Region:
Pineapple upside-down cake is a classic American dessert that originated in the United States in the early 20th century. While the exact origin is unclear, this sweet treat gained popularity during the mid-20th century and has remained a beloved dessert across the United States ever since. Pineapple upside-down cupcakes are a delightful twist on the traditional cake and are enjoyed by dessert lovers worldwide.

Indulge in the tropical flavors of pineapple upside-down cupcakes, a delightful dessert that combines the sweetness of pineapple with the rich flavor of caramelized brown sugar. These miniature treats are perfect for any occasion, from casual gatherings to elegant parties, and are sure to impress your family and friends. With their moist cake base and caramelized pineapple topping, pineapple upside-down cupcakes are a true crowd-pleaser.


  • 1/4 cup (1/2 stick) unsalted butter
  • 2/3 cup packed light brown sugar
  • 1 can (20 ounces) pineapple slices in juice, drained (reserve juice for batter)
  • Maraschino cherries, drained
  • 1 1/3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/2 cup granulated sugar
  • 1/4 cup vegetable oil
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1/2 cup pineapple juice (reserved from canned pineapple)

Optional Toppings:

  • Whipped cream or vanilla ice cream
  • Additional maraschino cherries for garnish


  • Ensure that the butter is softened at room temperature for easier mixing.
  • Use pineapple slices that are well-drained to prevent excess moisture in the cupcakes.
  • For extra flavor, consider adding a splash of rum to the pineapple topping.
  • Allow the cupcakes to cool in the pan for a few minutes before flipping them onto a serving platter to ensure that the topping stays intact.


  1. Preheat the oven to 350°F (175°C). Line a muffin tin with cupcake liners.
  2. In a small saucepan, melt the butter over medium heat. Stir in the brown sugar until well combined and slightly caramelized, about 2-3 minutes.
  3. Spoon the caramelized mixture evenly into the bottom of each cupcake liner.
  4. Place a pineapple slice in the center of each cupcake liner, pressing gently into the brown sugar mixture. Place a maraschino cherry in the center of each pineapple slice.
  5. In a medium bowl, whisk together the flour, baking powder, and salt.
  6. In a separate bowl, beat together the granulated sugar, vegetable oil, egg, and vanilla extract until smooth.
  7. Gradually add the dry ingredients to the wet ingredients, alternating with the pineapple juice, and mix until just combined.
  8. Divide the batter evenly among the cupcake liners, filling each about 2/3 full.
  9. Bake in the preheated oven for 18-20 minutes, or until a toothpick inserted into the center comes out clean.
  10. Remove from the oven and let the cupcakes cool in the pan for a few minutes.
  11. Carefully invert the cupcakes onto a serving platter or wire rack to cool completely.

Pineapple upside-down cupcakes are a delightful twist on the classic pineapple upside-down cake. These individual-sized treats feature moist and fluffy cake topped with caramelized brown sugar, juicy pineapple slices, and vibrant maraschino cherries. With their irresistible combination of sweet and tangy flavors, pineapple upside-down cupcakes are sure to be a hit at any gathering. Enjoy them warm or at room temperature, topped with whipped cream or vanilla ice cream for an extra special treat.

Nutritional Information:
(Serving Size: 1 cupcake, based on standard recipe yield)

  • Calories: 180 kcal
  • Total Fat: 7g
  • Saturated Fat: 2.5g
  • Cholesterol: 20mg
  • Sodium: 105mg
  • Total Carbohydrates: 28g
  • Dietary Fiber: 1g
  • Sugars: 18g
  • Protein: 2g

(Note: Nutritional information may vary depending on specific ingredients and portion sizes.)

Leave a Comment