Pineapple Upside Down Cupcakes Recipe

Get ready for a taste of paradise with these irresistible Pineapple Upside-Down Cupcakes! This family-favorite recipe delivers incredibly moist and delicious cupcakes, bursting with juicy pineapple and a sweet, caramelized topping. Perfect for parties, potlucks, or a special treat, these cupcakes are guaranteed to be a crowd-pleaser. Easy to make and even easier to devour!

Prep Time 20 mins

Cook Time 40 mins

Calories 287.3 kcal

Protein 5g

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The Forktionary Kitchen Team

Adapted from Food.com, then tested & standardized by Forktionary.

Ingredients for Pineapple Upside Down Cupcakes

1/2 cup (113g) softened butter + 1/4 cup (59ml) butter
Milk
Flour
Baking Powder
1/2 teaspoon salt
2 large eggs
Sugar
1 teaspoon vanilla extract
1/2 cup (113g) brown sugar
Maraschino Cherries
Pineapple rings (amount will depend on size of rings and cupcake liners)

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How to Make Pineapple Upside Down Cupcakes

Preheat oven to 350°F (175°C). Line a 12-cup muffin tin with cupcake liners.
In a medium saucepan, combine 1/2 cup (113g) brown sugar, 1/4 cup (59ml) butter, and 1/4 cup (60ml) pineapple juice. Cook over medium heat, stirring constantly, until butter is melted and sugar is dissolved.
Remove from heat and pour 1 tablespoon of the caramel mixture into the bottom of each cupcake liner.
Arrange pineapple rings on top of the caramel in each liner.
In a large bowl, cream together 1/2 cup (113g) softened butter and 1 cup (200g) granulated sugar until light and fluffy.
Beat in 2 large eggs one at a time, then stir in 1 teaspoon vanilla extract.
In a separate bowl, whisk together 1 1/2 cups (190g) all-purpose flour, 1 teaspoon baking soda, and 1/2 teaspoon salt.
Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
Fold in 1 cup (227g) crushed pineapple (drained).
Fill each cupcake liner about 2/3 full with batter.
Bake for 18-20 minutes, or until a toothpick inserted into the center comes out clean.
Let cupcakes cool in the muffin tin for a few minutes before inverting them onto a wire rack to cool completely.
Optional: Drizzle with extra caramel sauce or dust with powdered sugar before serving.