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Dessert / Pineapple Upside Down Cupcakes: A Delicious Twist on a Classic Dessert

Pineapple Upside Down Cupcakes: A Delicious Twist on a Classic Dessert

May 9, 2025 by JannaDessert

Pineapple upside down cupcakes are a delightful twist on the classic dessert that brings a tropical flair to any occasion. As a child, I remember the first time I tasted this sweet treat; the combination of caramelized pineapple and fluffy cake was simply irresistible. This recipe not only pays homage to the traditional pineapple upside down cake, which has roots dating back to the early 20th century, but it also offers a convenient, individual-sized version that is perfect for sharing or enjoying on your own.

People love pineapple upside down cupcakes for their vibrant flavors and unique presentation. The moist cake pairs beautifully with the juicy, sweet pineapple, creating a delightful contrast in both taste and texture. Plus, these cupcakes are incredibly easy to make, making them a go-to dessert for gatherings, potlucks, or simply a sweet treat at home. Join me as we dive into this delicious recipe that is sure to become a favorite in your household!

Pineapple upside down cupcakes this Recipe

Ingredients:

  • 1 cup all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup buttermilk
  • 1 can (20 oz) sliced pineapple in juice, drained
  • 1/2 cup maraschino cherries
  • 1/4 cup brown sugar
  • 1/4 cup unsalted butter, melted (for the topping)

Preparing the Topping

1. Start by preheating your oven to 350°F (175°C). This is crucial for ensuring that your cupcakes bake evenly and come out perfectly fluffy. 2. In a small bowl, combine the melted butter and brown sugar. Mix them together until they form a smooth paste. This will be the base for your pineapple topping. 3. Next, take a 12-cup muffin tin and grease it lightly with non-stick spray or additional melted butter. This will help prevent the cupcakes from sticking. 4. Spoon about a teaspoon of the brown sugar mixture into the bottom of each muffin cup. This will create a sweet caramel layer that will be the base of your pineapple upside-down cupcakes. 5. Now, place a slice of pineapple on top of the brown sugar mixture in each cup. If you have smaller pieces, you can cut them to fit. Don’t forget to add a maraschino cherry in the center of each pineapple slice for that classic upside-down look!

Preparing the Batter

6. In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. This step is important as it ensures that your dry ingredients are evenly distributed. 7. In a large mixing bowl, cream together the softened butter and granulated sugar using an electric mixer on medium speed. Beat them until the mixture is light and fluffy, which should take about 3-4 minutes. 8. Add the eggs, one at a time, mixing well after each addition. Then, stir in the vanilla extract. This will add a lovely flavor to your cupcakes. 9. Now, it’s time to incorporate the dry ingredients. Gradually add the flour mixture to the butter mixture, alternating with the buttermilk. Start and end with the flour mixture. Mix until just combined; be careful not to overmix, as this can lead to dense cupcakes. 10. Once the batter is smooth and well combined, it’s ready to be poured into the muffin tin.

Filling the Muffin Tin

11. Using a spoon or an ice cream scoop, carefully fill each muffin cup with the batter. Aim to fill each cup about 2/3 full to allow room for the cupcakes to rise. 12. Gently tap the muffin tin on the counter to remove any air bubbles and ensure the batter settles evenly.

Baking the Cupcakes

13. Place the muffin tin in the preheated oven and bake for 18-22 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. Keep an eye on them, as oven temperatures can vary. 14. Once baked, remove the muffin tin from the oven and let it cool for about 5 minutes. This will make it easier to remove the cupcakes without breaking them.

Removing and Serving the Cupcakes

15. After the cupcakes have cooled slightly, carefully run a knife around the edges of each muffin cup to loosen them. 16. Place a wire rack over the muffin tin and flip it upside down. Gently tap the bottom of the tin to release the cupcakes. If any pineapple or cherry pieces stick to the tin, simply place them back on top of the cupcakes. 17. Allow the cupcakes to cool completely on the wire rack. This will help them set and make them easier to handle.

Enjoying Your Pineapple Upside Down Cupcakes

18. Once the cupcakes are completely cool, they are ready to be served! You can enjoy them as they are, or you can add a dollop of whipped cream or a scoop of vanilla ice cream on top for an extra treat. 19. These cupcakes are perfect for any occasion, whether it’s a birthday party, a summer barbecue, or just a sweet treat for yourself. The combination of the sweet pineapple, the rich buttery cake, and the cherry on Pineapple upside down cupcakes

Conclusion:

In conclusion, these pineapple upside down cupcakes are an absolute must-try for anyone looking to add a delightful twist to their dessert repertoire. The combination of sweet, caramelized pineapple and fluffy vanilla cake creates a flavor explosion that is both nostalgic and refreshing. Plus, the individual cupcake format makes them perfect for sharing at parties, picnics, or simply enjoying at home with family. If you want to get creative, consider adding a splash of coconut milk to the batter for a tropical flair, or swap out the pineapple for other fruits like peaches or cherries for a fun variation. You can also top them with a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent treat. I encourage you to give this recipe a try and experience the joy of baking these delightful cupcakes. Once you do, I’d love to hear about your experience! Share your thoughts, any variations you tried, or even a picture of your delicious creations. Let’s spread the love for these pineapple upside down cupcakes together! Happy baking! Print
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Pineapple Upside Down Cupcakes: A Delicious Twist on a Classic Dessert


  • Author: Maria
  • Total Time: 35-40 minutes
  • Yield: 12 cupcakes 1x
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Description

Enjoy these Pineapple Upside Down Cupcakes, featuring a moist buttery cake topped with caramelized pineapple and cherries. Perfect for any occasion, these delightful treats are sure to impress your guests!


Ingredients

Scale
  • 1 cup all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup buttermilk
  • 1 can (20 oz) sliced pineapple in juice, drained
  • 1/2 cup maraschino cherries
  • 1/4 cup brown sugar
  • 1/4 cup unsalted butter, melted (for the topping)

Instructions

  1. Preheat your oven to 350°F (175°C).
  2. In a small bowl, combine the melted butter and brown sugar until smooth. This will be your topping base.
  3. Grease a 12-cup muffin tin with non-stick spray or melted butter.
  4. Spoon about a teaspoon of the brown sugar mixture into the bottom of each muffin cup.
  5. Place a slice of pineapple on top of the brown sugar mixture in each cup, adding a maraschino cherry in the center of each pineapple slice.
  6. In a medium bowl, whisk together the flour, baking powder, baking soda, and salt.
  7. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy (about 3-4 minutes).
  8. Add the eggs one at a time, mixing well after each addition, then stir in the vanilla extract.
  9. Gradually add the flour mixture to the butter mixture, alternating with the buttermilk, starting and ending with the flour mixture. Mix until just combined.
  10. Fill each muffin cup about 2/3 full with the batter.
  11. Gently tap the muffin tin on the counter to remove air bubbles.
  12. Bake for 18-22 minutes, or until a toothpick inserted into the center comes out clean.
  13. Remove the muffin tin from the oven and let it cool for about 5 minutes.
  14. Run a knife around the edges of each muffin cup to loosen the cupcakes.
  15. Place a wire rack over the muffin tin and flip it upside down to release the cupcakes.
  16. Allow the cupcakes to cool completely on the wire rack.
  17. Serve as is, or top with whipped cream or vanilla ice cream for an extra treat.

Notes

  • Ensure the butter is softened for easy creaming with sugar.
  • Be careful not to overmix the batter to keep the cupcakes light and fluffy.
  • These cupcakes can be stored in an airtight container for up to 3 days.
  • Prep Time: 15 minutes
  • Cook Time: 22 minutes

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