Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert. These individual treats feature caramelized pineapple slices and maraschino cherries atop a moist and fluffy vanilla cupcake. Perfect for parties, gatherings, or simply as a sweet indulgence, these cupcakes are sure to impress with their tropical flavor and charming presentation.


For the Pineapple Upside Down Topping:

  • 1/4 cup unsalted butter
  • 1/2 cup brown sugar, packed
  • 6 slices pineapple rings, canned
  • 12 maraschino cherries, drained

For the Cupcake Batter:

  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup milk


  1. Preheat the Oven:
  • Preheat your oven to 350°F (175°C). Line a muffin tin with cupcake liners and set aside.
  1. Prepare the Pineapple Upside Down Topping:
  • In a small saucepan, melt the unsalted butter over medium heat. Stir in the brown sugar until dissolved and the mixture is smooth.
  • Divide the butter and sugar mixture evenly among the muffin cups, filling the bottom of each cup.
  • Place a pineapple ring on top of the butter and sugar mixture in each muffin cup. Place a maraschino cherry in the center of each pineapple ring.
  1. Make the Cupcake Batter:
  • In a medium bowl, whisk together the all-purpose flour, baking powder, and salt. Set aside.
  • 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, mixing well after each addition. Stir in the vanilla extract.
  • Gradually add the dry ingredients to the wet ingredients, alternating with the milk, until a smooth batter forms.
  1. Assemble the Cupcakes:
  • Spoon the cupcake batter evenly over the pineapple slices and cherries in the muffin cups, filling each cup about 2/3 full.
  1. Bake the Cupcakes:
  • Transfer the muffin tin to the preheated oven and bake for 18-20 minutes, or until the cupcakes are golden brown and a toothpick inserted into the center comes out clean.
  1. Cool and Serve:
  • Remove the cupcakes from the oven and allow them to cool in the muffin tin for 5 minutes.
  • Carefully invert the cupcakes onto a wire rack to cool completely before serving.


  • Be sure to use canned pineapple slices that are packed in juice, not syrup.
  • If you prefer a more intense pineapple flavor, you can brush the pineapple slices with pineapple juice before placing them in the muffin cups.
  • These cupcakes are best served the same day they are made, but they can be stored in an airtight container at room temperature for up to 2 days.

Pineapple Upside Down Cupcakes offer all the classic flavors of the traditional dessert in individual, handheld servings. With their caramelized pineapple topping and moist vanilla cake base, these cupcakes are a nostalgic treat that evoke memories of sunny days and tropical getaways. Serve them at your next gathering for a sweet taste of paradise.

Nutritional Information:
(Serving Size: 1 cupcake)

  • Calories: 240 kcal
  • Total Fat: 11g
  • Saturated Fat: 6g
  • Trans Fat: 0g
  • Cholesterol: 55mg
  • Sodium: 150mg
  • Total Carbohydrates: 33g
  • Dietary Fiber: 1g
  • Sugars: 22g
  • Protein: 3g

(Note: Nutritional information is approximate and may vary depending on specific ingredients and serving size.)

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