Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes are a delightful twist on the classic pineapple upside down cake. These individual-sized treats are not only visually appealing but also incredibly delicious. The combination of caramelized pineapple, sweet cake, and a cherry on top is simply irresistible. Whether you are hosting a party or simply craving a sweet treat, these cupcakes are sure to impress. Follow this easy recipe to create your own batch of Pineapple Upside Down Cupcakes.


  • 1 can of pineapple slices
  • 1/4 cup of unsalted butter, melted
  • 1/2 cup of brown sugar
  • Maraschino cherries
  • 1 1/2 cups of all-purpose flour
  • 1 1/2 teaspoons of baking powder
  • 1/4 teaspoon of salt
  • 1/2 cup of unsalted butter, softened
  • 1 cup of granulated sugar
  • 2 large eggs
  • 1 teaspoon of vanilla extract
  • 1/2 cup of milk


Step 1: Prepare the Pineapple Topping

Preheat your oven to 350°F (175°C). Drain the pineapple slices and reserve the juice for later. In a muffin tin, place a teaspoon of melted butter into each cup. Sprinkle brown sugar evenly over the butter. Arrange one pineapple slice on top of the sugar-butter mixture in each cup. Place a cherry in the center of each pineapple slice.

Step 2: Make the Cupcake Batter

In a medium-sized bowl, whisk together the flour, baking powder, and salt. In a separate large bowl, cream together the softened butter and granulated sugar until light and fluffy. Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract. Gradually add the dry ingredients to the butter mixture, alternating with the reserved pineapple juice and milk. Mix until just combined.

Step 3: Assemble and Bake

Spoon the cupcake batter over the pineapple slices in the muffin tin, filling each cup about 2/3 full. Smooth the tops with the back of a spoon. Place the tin in the preheated oven and bake for 18-20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.

Step 4: Cool and Serve

Remove the cupcakes from the oven and let them cool in the tin for 5 minutes. Carefully invert the tin onto a wire rack, allowing the cupcakes to release onto the rack. Gently lift the tin off the cupcakes. If any pineapple slices stick to the tin, simply place them back on top of the cupcakes. Allow the cupcakes to cool completely before serving.

These Pineapple Upside Down Cupcakes are best enjoyed fresh, but they can be stored in an airtight container for up to three days. Serve them as a delightful dessert or enjoy them with a cup of tea or coffee. The combination of sweet pineapple, caramelized sugar, and moist cake is sure to satisfy your cravings. So, gather your ingredients and get ready to indulge in these irresistible treats!

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