Pineapple Upside-Down Cupcakes Recipe

Indulge in these delightful individual pineapple upside-down cupcakes that perfectly blend the sweetness of pineapple with the moistness of cake. They’re a charming twist on the classic dessert, easy to make and sure to impress!


  • 1/4 cup unsalted butter
  • 2/3 cup packed brown sugar
  • 1 can (20 ounces) pineapple slices, drained
  • Maraschino cherries
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons 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 your oven to 350°F (175°C).
  2. In a saucepan, melt 1/4 cup of butter over low heat. Once melted, stir in the brown sugar until well combined. Remove from heat.
  3. Spoon the butter and sugar mixture evenly into the bottoms of a greased muffin tin, filling each cup about halfway.
  4. Place a pineapple slice into each cup on top of the butter and sugar mixture. If needed, you can cut the slices to fit.
  5. Place a maraschino cherry in the center of each pineapple slice.
  6. In a mixing bowl, whisk together the flour, baking powder, and salt until well combined.
  7. In another bowl, cream together the softened butter and granulated sugar until light and fluffy.
  8. Beat in the eggs, one at a time, then stir in the vanilla extract.
  9. Gradually add the dry ingredients to the wet mixture, alternating with the milk, until the batter is smooth.
  10. Spoon the batter evenly over the pineapple slices in the muffin tin, filling each cup about three-quarters full.
  11. Bake in the preheated oven for 20-25 minutes or until a toothpick inserted into the center of a cupcake comes out clean.
  12. Allow the cupcakes to cool in the tin for about 5 minutes, then carefully invert the tin onto a wire rack to release the cupcakes. Let them cool completely.
  13. Once cooled, serve and enjoy these delightful pineapple upside-down cupcakes!

These cupcakes are perfect for any occasion, from casual gatherings to special celebrations. They’re sure to be a hit with friends and family alike!

Leave a Comment