Pineapple Upside-Down Cupcakes



Embrace the essence of tropical sweetness with our meticulously crafted Pineapple Upside-Down Cupcakes. This recipe transforms the classic pineapple upside-down cake into irresistible cupcakes, combining moist sponge, tangy pineapple, and the sweet burst of maraschino cherries. Ideal for celebrations, family gatherings, or as a delightful treat, these cupcakes are not only a feast for the taste buds but also a vibrant spectacle that promises to elevate any dessert table.


To begin, gather the following high-quality ingredients to ensure your cupcakes are both delicious and visually stunning:

  • 1 can (20 oz) of sliced pineapple, thoroughly drained to preserve the concentrated flavor.
  • 1 box of premium yellow cake mix for a perfectly moist base.
  • 3 large eggs, ensuring the batter has the right consistency and richness.
  • 1 1/2 cups of milk to add moisture and lightness to the cake mix.
  • 1/3 cup of butter, melted, to blend smoothly into the batter for a rich, buttery flavor.
  • 2/3 cup of packed brown sugar, creating a caramelized foundation that complements the pineapple.
  • 24 maraschino cherries, adding a sweet and colorful touch to each cupcake.

How To Make Pineapple Upside-Down Cupcakes

Preparation Stage:

  1. Preheat your oven to 350°F (175°C) to ensure an even baking environment for the cupcakes.
  2. Spray 24 regular-sized muffin cups with non-stick cooking spray to prevent the cupcakes from sticking and to ensure a smooth release after baking.

Crafting the Base:

  1. Carefully cut each pineapple slice into 3 pieces. This step ensures that each cupcake will have an even distribution of pineapple, offering a perfect balance of tartness and sweetness.
  2. In a large mixing bowl, combine the yellow cake mix, milk, and eggs. Start mixing at low speed for 30 seconds to incorporate the ingredients gently, then increase to medium speed for 2 minutes. This method ensures the batter achieves the desired smoothness and airiness.

Creating the Caramelized Layer:

  1. In a smaller bowl, mix the melted butter with the brown sugar until well combined. This mixture will create a delectable caramelized layer at the bottom of each cupcake, enriching the overall flavor profile.
  2. Place 1 teaspoon of the butter and brown sugar mixture into each muffin cup. This precise amount guarantees a perfect caramelization without overwhelming the cake.
  3. Top the butter mixture with 2 pieces of pineapple and a maraschino cherry in the center. This arrangement not only infuses the cupcakes with flavor but also creates a stunning visual when inverted.

Baking to Perfection:

  1. Distribute the cake batter evenly among the prepared muffin cups, ensuring each is filled just right to allow for proper rising without overflowing.
  2. Bake in the preheated oven for 20 to 25 minutes. The exact timing ensures the cupcakes are cooked perfectly – moist on the inside with a slightly golden top.
  3. After baking, allow the cupcakes to cool for 5 minutes. This brief cooling period makes the inversion process smoother, maintaining the cupcakes’ structural integrity and aesthetic appeal.

The Grand Reveal:

  1. Carefully run a knife around the edges of the cupcakes to loosen them from the pan. This precision ensures that the caramelized bottom, now the top, remains intact and beautifully presented.
  2. Invert the cupcakes onto a cookie sheet or serving platter. This moment of transformation showcases the caramelized pineapple and cherry topping in all its glory, promising a delightful contrast of textures and flavors.

Serving Suggestions

Serve these Pineapple Upside-Down Cupcakes warm, accompanied by sweet whipped cream or vanilla ice cream. The warmth of the cupcakes melts the cream slightly, creating an irresistible combination of flavors and textures that promise to enchant your guests.


Our Pineapple Upside-Down Cupcakes recipe offers a modern twist on a classic dessert, combining the comfort of a sponge cake with the exotic flair of pineapple and cherries. Each step in this recipe is designed to ensure that the cupcakes you create are not only delicious but also visually appealing, making them the perfect addition to any event or a special treat for your loved ones.