Pineapple Upside Down Cupcakes


🍍 Pineapple Upside Down Cupcakes: A Tropical Twist on a Classic Favorite

Dive into a whimsical world of sweetness and flavor with these Pineapple Upside Down Cupcakes! A delightful twist on the traditional Pineapple Upside Down Cake, this recipe transforms the classic dessert into adorable, single-serving cupcakes that are perfect for any occasion. Whether it’s a sunny brunch, a cozy family gathering, or just a sweet craving, these cupcakes are sure to bring a burst of tropical joy to your table.

In each little cake, you’ll discover the magic of caramelized brown sugar, the cheerful brightness of maraschino cherries, and the tangy zest of crushed pineapple, all nestled beneath a moist, fluffy pillow of pineapple-infused cake. It’s like a mini vacation in every bite!

So, preheat your ovens and get ready to indulge in these charming and irresistible Pineapple Upside Down Cupcakes. They’re not just desserts; they’re tiny, edible celebrations of joy!


  1. For the Topping:
    • ½ cup sweet cream butter, melted
    • 1 ½ cups light brown sugar
    • 24 maraschino cherries
    • 20 oz can crushed pineapple
  2. For the Cake:
    • 1 package (18.25 oz) pineapple cake mix
    • 3 large eggs
    • 1 ½ cups pineapple juice
    • ½ cup canola oil
  3. For Garnish:
    • 1 Tbsp powdered sugar


  1. Preheat and Prep:
    • Position your oven rack in the middle.
    • Preheat the oven to 350°F (175°C).
    • Prepare muffin cups with nonstick baking spray.
  2. Create the Topping:
    • In each muffin cup, add 1 teaspoon of melted butter.
    • Top the melted butter with 1 tablespoon of light brown sugar.
    • Place one maraschino cherry in the center of each cup.
    • Add a heaping tablespoon of crushed pineapple on top of the cherry, pressing down with the back of a spoon.
  3. Make the Cake Batter:
    • In a mixer bowl, combine the pineapple cake mix, eggs, pineapple juice, and canola oil.
    • Start mixing on low until just moistened (about 30 seconds).
    • Increase to medium speed and mix for 2 minutes.
  4. Assemble and Bake:
    • Scoop the batter into each muffin well, filling just below the top.
    • Bake for 20 minutes. Check doneness with a toothpick; it should come out clean.
    • Let the cupcakes cool for 5 minutes, then flip them onto a cooling rack.
  5. Serve:
    • The cherry should now be beautifully presented on top.
    • Dust with powdered sugar before serving.


  • Even Distribution: Ensure even distribution of the topping ingredients in each muffin cup for a consistent look and taste.
  • Don’t Overfill: Be careful not to overfill the muffin wells with batter to avoid spill-over during baking.
  • Cooling Time: Allow adequate cooling time before flipping to prevent the cupcakes from falling apart.

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