Pineapple Upside-Down Cupcakes: Bite-Sized Tropical Delights

Transport yourself to a tropical paradise with our irresistible Pineapple Upside-Down Cupcakes. These delectable treats capture the essence of a classic pineapple upside-down cake, but in adorable individual servings. Each moist and flavorful cupcake is crowned with caramelized pineapple rings and a maraschino cherry, creating a feast for both the eyes and the taste buds. Get ready to embark on a sweet and tangy adventure with every bite!


  • 1 can Pineapple Rings (20 oz), drained
  • 1/4 cup Unsalted Butter, melted
  • 1/2 cup Brown Sugar, packed
  • 12 Maraschino Cherries
  • 1 1/2 cups All-Purpose Flour
  • 1 1/2 teaspoons Baking Powder
  • 1/4 teaspoon Salt
  • 1/2 cup Unsalted Butter, softened
  • 1 cup Granulated Sugar
  • 2 large Eggs
  • 1 teaspoon Vanilla Extract
  • 1/2 cup Pineapple Juice (reserved from the canned pineapple rings)
  • 1/4 cup Milk

Let’s Unveil the Tropical Delights:

  1. Preheat your oven to 350 degrees Fahrenheit (175 degrees Celsius). Prepare a muffin tin by greasing the cavities or lining them with cupcake liners for easy removal.
  2. Now, it’s time to create the luscious caramelized pineapple topping. Take the melted unsalted butter and evenly distribute it among the prepared muffin tin cavities. Sprinkle the brown sugar over the melted butter, ensuring each cavity gets a sweet coating.
  3. Place a pineapple ring on top of the butter and brown sugar mixture in each cavity. Press them gently to create a snug fit. In the center of each pineapple ring, nestle a maraschino cherry, adding a pop of vibrant color and tangy sweetness.
  4. It’s time to prepare the cupcake batter. In a mixing bowl, whisk together the all-purpose flour, baking powder, and salt. Set this dry mixture aside for now.
  5. In another bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy. This will create a base for the cupcake batter that is both rich and smooth.
  6. Add the eggs, one at a time, to the creamed butter and sugar mixture, ensuring each egg is fully incorporated before adding the next. Stir in the vanilla extract, infusing the batter with its delightful aroma.
  7. Now, it’s time to add a tropical twist to the cupcake batter. Combine the reserved pineapple juice (from the canned pineapple rings) with the milk, creating a burst of pineapple flavor. Gradually add this pineapple juice mixture to the creamed butter and sugar mixture, alternating with the dry mixture (flour, baking powder, and salt). Begin and end with the dry mixture, ensuring everything is well combined after each addition.
  8. With the cupcake batter prepared, carefully spoon it over the pineapple rings and cherries in the muffin tin cavities. Fill each cavity approximately three-quarters full, allowing room for the cupcakes to rise and create a fluffy texture.
  9. Place the muffin tin in the preheated oven and bake for about 20-25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. Be sure not to overbake, as we want these little tropical delights to remain moist and tender.
  10. Once the cupcakes are baked to perfection, remove them from the oven and let them cool in the muffin tin for a few minutes. Then, carefully transfer each cupcake to a wire rack to cool completely. As they cool, the tantalizing aroma of caramelized pineapple will fill your kitchen, making it impossible to resist a taste.
  11. Finally, the moment you’ve been waiting for—indulge in the tropical delight of Pineapple Upside-Down Cupcakes. With their caramelized pineapple topping and tender crumb, each bite will transport you to a sunny island getaway.

These Pineapple Upside-Down Cupcakes are perfect for any occasion, whether it’s a summertime gathering, a tropical-themed party, or simply a sweet treat to brighten your day. Share them with friends and loved ones, and watch as their faces light up with delight. Get ready to savor the tropical flavors and create unforgettable memories with these bite-sized delights. Enjoy!

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