Pineapple Upside-Down Cupcakes


Sumptuous Pineapple Upside-Down Cupcakes

Get ready to elevate your baking game with our delectable Pineapple Upside-Down Cupcakes recipe! These delightful treats combine the tropical sweetness of pineapple with the irresistible allure of moist, fluffy cupcakes. Each bite is a symphony of flavors, from the caramelized brown sugar topping to the juicy burst of maraschino cherry in the center. Whether you’re hosting a party, celebrating a special occasion, or simply craving a taste of paradise, these cupcakes are sure to impress.



Pineapple Upside-Down Cake is a classic dessert that has been delighting taste buds for generations. With our innovative twist on this timeless treat, we’ve transformed it into individual cupcakes that are as adorable as they are delicious. Perfect for any occasion, these Pineapple Upside-Down Cupcakes are guaranteed to be a hit with friends and family alike.



  • 1 can (20 oz) sliced pineapple, drained
  • 1 box yellow cake mix
  • 3 eggs
  • 1 1/2 cups milk
  • 1/3 cup butter, melted
  • 2/3 cup packed brown sugar
  • 24 maraschino cherries


  1. Preheat Oven: Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners.
  2. Prepare Pineapple Topping: In a small bowl, mix together the melted butter and brown sugar until well combined. Spoon a tablespoon of the mixture into each cupcake liner, spreading it evenly to coat the bottom.
  3. Add Pineapple Slices: Place a pineapple slice on top of the brown sugar mixture in each cupcake liner. If needed, you can cut the slices to fit.
  4. Place Cherries: Place a maraschino cherry in the center of each pineapple slice, gently pressing it down.
  5. Prepare Cake Batter: In a large mixing bowl, combine the cake mix, eggs, and milk according to the package instructions. Mix until smooth and well combined.
  6. Fill Cupcake Liners: Pour the cake batter over the pineapple slices and cherries in each cupcake liner, filling them about 2/3 full.
  7. Bake: Bake in the preheated oven for 18-20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
  8. Cool and Serve: Allow the cupcakes to cool in the muffin tin for a few minutes, then transfer them to a wire rack to cool completely. Once cooled, gently remove the cupcake liners and serve.

Cook Notes and Variations:

  • Fresh Pineapple: If you prefer, you can use fresh pineapple instead of canned. Simply slice the pineapple into rings and remove the core before placing them in the cupcake liners.
  • Mini Cupcakes: For bite-sized treats, use a mini muffin tin and adjust the baking time accordingly.
  • Nutty Addition: Add a sprinkle of chopped pecans or walnuts to the brown sugar mixture for extra crunch and flavor.

Frequently Asked Questions (FAQs):

Q: Can I use a different type of cake mix? A: Yes, feel free to experiment with different cake mixes such as vanilla, pineapple, or even coconut for a tropical twist.


Q: Can I make these cupcakes ahead of time? A: Absolutely! These cupcakes can be made in advance and stored in an airtight container at room temperature for up to three days. Alternatively, you can freeze them for longer storage and thaw them before serving.


Q: Can I use fresh cherries instead of maraschino cherries? A: While maraschino cherries are traditional for Pineapple Upside-Down Cake, you can certainly use fresh cherries if you prefer. Just be sure to pit them before placing them on top of the pineapple slices.


Q: How do I prevent the cupcakes from sticking to the liners? A: To prevent sticking, make sure the cupcakes are completely cooled before removing them from the liners. You can also lightly grease the liners with cooking spray before adding the brown sugar mixture.

Keto and Low-Carb Versions:

For those following a keto or low-carb lifestyle, here’s how to adapt this recipe:

  • Almond Flour Batter: Replace the yellow cake mix with a combination of almond flour, eggs, and a low-carb sweetener such as erythritol.
  • Sugar-Free Sweetener: Use a sugar-free sweetener in place of the brown sugar, and opt for fresh pineapple or pineapple in natural juice instead of canned fruit.

By making these simple substitutions, you can enjoy a keto-friendly version of Pineapple Upside-Down Cupcakes without sacrificing flavor or texture.

Indulge in a taste of paradise with our irresistible Pineapple Upside-Down Cupcakes. With their tropical flavors and charming presentation, these cupcakes are sure to be a hit at any gathering or celebration. Whether you’re baking for a crowd or simply treating yourself to a sweet indulgence, these cupcakes are guaranteed to bring a smile to your face. So why wait? Whip up a batch today and savor the deliciousness of these delightful treats!