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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 12, 2025 by BriannaDessert

Pineapple upside down cupcakes are a delightful twist on the classic dessert that brings a tropical flair to any occasion. Imagine biting into a moist, fluffy cupcake topped with caramelized pineapple and a cherry, creating a perfect balance of sweetness and tang. This recipe has its roots in the beloved pineapple upside down cake, which gained popularity in the mid-20th century, becoming a staple at family gatherings and celebrations. What I love most about pineapple upside down cupcakes is their individual serving size, making them not only convenient but also a fun treat to share with friends and family. The combination of the rich buttery flavor and the juicy pineapple creates a taste sensation that is simply irresistible. Whether you’re hosting a party or just looking to satisfy your sweet tooth, these cupcakes are sure to impress!

Pineapple upside down cupcakes

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
  • Cooking spray or additional butter for greasing

Preparing the Topping

1. Start by preheating your oven to 350°F (175°C). This ensures that your cupcakes bake evenly and come out perfectly fluffy. 2. In a small bowl, combine the brown sugar and a tablespoon of the pineapple juice from the can. Mix until the sugar is slightly dissolved. This will create a sweet syrup that will be the base for your pineapple topping. 3. Grease a standard muffin tin with cooking spray or butter. Make sure to coat each cup generously to prevent sticking. 4. Spoon about a teaspoon of the brown sugar mixture into the bottom of each muffin cup. This will create a delicious caramelized layer once the cupcakes are baked. 5. Place a slice of pineapple on top of the brown sugar mixture in each cup. If the slices are too large, feel free to cut them in half. 6. Add a maraschino cherry in the center of each pineapple slice. This adds a pop of color and a sweet surprise in every bite.

Preparing the Batter

7. In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. This helps to evenly distribute the leavening agents throughout the flour. 8. In a large mixing bowl, cream together the softened butter and granulated sugar using an electric mixer on medium speed. Beat until the mixture is light and fluffy, about 3-4 minutes. 9. 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. 10. Gradually add the dry ingredients to the wet mixture, alternating with the buttermilk. Start with a third of the flour mixture, then half of the buttermilk, and continue alternating until everything is combined. Be careful not to overmix; a few lumps are perfectly fine. 11. Once the batter is smooth, use a spatula to scrape down the sides of the bowl to ensure everything is well incorporated.

Filling the Muffin Tin

12. 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 rising. 13. Gently tap the muffin tin on the counter to remove any air bubbles and to help the batter settle evenly.

Baking the Cupcakes

14. 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 baking times can vary based on your oven. 15. Once baked, remove the muffin tin from the oven and let it cool for about 5 minutes. This allows the cupcakes to set slightly and makes them easier to remove.

Removing and Serving the Cupcakes

16. To remove the cupcakes, run a knife around the edges of each muffin cup to loosen them. Then, carefully invert the muffin tin onto a wire rack or a large plate. Give it a gentle tap to release the cupcakes. 17. If any of the pineapple or cherry topping sticks to the muffin tin, simply lift it out and place it back on top of the cupcake. 18. Allow the cupcakes to cool completely before serving. This will help the flavors meld together and make them even more delicious.

Storing the Cupcakes

19. If you have any leftovers (which is rare because they’re so good!), store the cupcakes in an airtight container at room temperature for up to 3 days. You can also refrigerate them for up to a week, but they are best enjoyed fresh. 20. For longer storage, consider freezing the cupcakes. Place them in a single layer on a baking sheet until frozen solid, then transfer them to a freezer-safe container. They can be frozen for up to 3

Pineapple upside down cupcakes

Conclusion:

In summary, 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. For serving suggestions, consider pairing these cupcakes with a scoop of vanilla ice cream or a dollop of whipped cream for an extra indulgent treat. You can also experiment with variations by adding a splash of coconut milk to the batter for a tropical flair or incorporating chopped nuts for added texture. The possibilities are endless! I encourage you to give this recipe a try and experience the joy of baking these delightful pineapple upside down cupcakes. Once you do, I would love to hear about your experience! Share your thoughts, any tweaks you made, or even a photo of your delicious creations. Let’s spread the love for this scrumptious dessert together!

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

Print Recipe

Enjoy these Pineapple Upside-Down Cupcakes, featuring a luscious caramelized pineapple and cherry topping on a light vanilla cupcake. Perfect for any celebration, they combine tropical flavors with an eye-catching presentation that will delight your guests.

  • Author: Dottie
  • Prep Time: 15 minutes
  • Cook Time: 22 minutes
  • Total Time: 37 minutes
  • Yield: 12 cupcakes 1x

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
  • Cooking spray or additional butter for greasing

Instructions

  1. Preheat your oven to 350°F (175°C).
  2. In a small bowl, combine the brown sugar and a tablespoon of the pineapple juice. Mix until slightly dissolved.
  3. Grease a standard muffin tin with cooking spray or 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.
  6. Add a maraschino cherry in the center of each pineapple slice.
  7. In a medium bowl, whisk together the flour, baking powder, baking soda, and salt.
  8. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy (about 3-4 minutes).
  9. Add the eggs one at a time, mixing well after each addition, then stir in the vanilla extract.
  10. Gradually add the dry ingredients to the wet mixture, alternating with the buttermilk, until combined. Do not overmix.
  11. Scrape down the sides of the bowl to ensure everything is well incorporated.
  12. Fill each muffin cup about 2/3 full with the batter.
  13. Gently tap the muffin tin on the counter to remove air bubbles.
  14. Bake for 18-22 minutes, or until a toothpick inserted into the center comes out clean.
  15. Remove from the oven and let cool for about 5 minutes.
  16. Run a knife around the edges of each muffin cup to loosen them, then invert the muffin tin onto a wire rack or plate.
  17. If any topping sticks, simply lift it out and place it back on top of the cupcake.
  18. Allow the cupcakes to cool completely before serving.
  19. Store leftovers in an airtight container at room temperature for up to 3 days or refrigerate for up to a week.
  20. For longer storage, freeze the cupcakes in a single layer until solid, then transfer to a freezer-safe container for up to 3 months.

Notes

  • Ensure the butter is softened for easy creaming with the sugar.
  • You can adjust the amount of pineapple and cherries based on your preference.
  • These cupcakes are best enjoyed fresh but can be stored or frozen for later enjoyment.

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