How to Make Pineapple Upside-Down Cupcakes from Scratch

Experience the charm of a classic dessert reimagined into bite-sized delights with these Pineapple Upside-Down Cupcakes. Combining the tropical sweetness of pineapple with the rich, caramelized flavor of brown sugar, these cupcakes invert the traditional presentation of a beloved cake into individual portions that are perfect for sharing. Each cupcake offers a moist, flavorful base topped with a perfectly placed pineapple ring and a cherry, capturing the essence of the original dessert in a fun and convenient format. Whether you’re hosting a party, looking for a unique treat to bake, or simply craving something sweet and fruity, these cupcakes are sure to impress.




Why You’ll Love Pineapple Upside-Down Cupcakes:

  • Individual Portions: Easy to serve and enjoy without the need for slicing.
  • Tropical Flavors: The pineapple and cherry topping adds a bright, fruity taste that’s perfect for any season.
  • Visually Appealing: Each cupcake is a mini masterpiece, with a caramelized pineapple and cherry presentation that looks as good as it tastes.
  • Simple and Fun to Make: A delightful baking project that’s both easy to prepare and rewarding to complete.

Ingredients Notes For Pineapple Upside-Down Cupcakes:

  • Pineapple Rings: Canned pineapple rings work best for consistent size and sweetness. You can also use fresh pineapple if preferred.
  • Maraschino Cherries: Adds a pop of color and sweet flavor to each cupcake.
  • Brown Sugar: Creates a rich, caramel-like layer that complements the pineapple.
  • Cake Batter: A simple vanilla or yellow cake batter serves as the base. You can use a boxed mix for convenience or your favorite homemade recipe.
  • Butter: Used to grease the muffin tins and mix with the brown sugar for the topping.

Recipe Steps:

  1. Preheat and Prepare: Preheat your oven to the temperature specified by your cake batter recipe. Grease the muffin tins with butter, then sprinkle brown sugar into each cup.
  2. Arrange Toppings: Place a pineapple ring in each muffin cup, trimming if necessary to fit. Add a maraschino cherry in the center of each pineapple ring.
  3. Add Batter: Prepare the cake batter according to your recipe or the boxed mix instructions. Pour the batter over the pineapple and cherries, filling each muffin cup about ¾ full.
  4. Bake: Bake according to the cake batter instructions, until the cupcakes are golden and a toothpick inserted into the center comes out clean.
  5. Invert and Serve: Let the cupcakes cool in the pan for a few minutes, then carefully invert them onto a serving tray. Serve warm or at room temperature.

Storage Options:

  • Room Temperature: Store the cupcakes in an airtight container at room temperature for up to 2 days.
  • Refrigerate: For longer storage, keep them in the refrigerator for up to 5 days. Allow to come to room temperature before serving.



How to Make Pineapple Upside-Down Cupcakes from Scratch

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Author: Maria


For the Topping (which will be at the bottom):

  • 1/4 cup unsalted butter melted
  • 2/3 cup brown sugar packed
  • 1 can 20 ounces pineapple slices in juice, drained and juice reserved
  • Maraschino cherries

For the Cupcake Batter:

  • 1 and 1/3 cups all-purpose flour
  • 2/3 cup granulated sugar
  • 2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter softened
  • 1/2 cup reserved pineapple juice
  • 2 eggs
  • 1 teaspoon vanilla extract


Preheat Oven and Prepare Muffin Tins:

  • Preheat your oven to 350°F (175°C). Grease a 12-cup muffin tin or line it with cupcake liners.

Prepare Pineapple and Topping:

  • Cut the pineapple slices into small pieces that will fit into the bottom of each muffin cup. Mix the melted butter and brown sugar together, and place a teaspoon of this mixture into the bottom of each muffin cup. Place a piece of pineapple on top of the sugar mixture in each cup, and add a maraschino cherry in the center of the pineapple.

Make the Cupcake Batter:

  • In a large bowl, whisk together the flour, granulated sugar, baking powder, and salt. Add the softened butter, pineapple juice, eggs, and vanilla extract. Beat with an electric mixer on medium speed until the batter is smooth and well combined.

Assemble Cupcakes:

  • Spoon the batter over the pineapple pieces in the muffin cups, filling each about 3/4 full.


  • Bake for 20-25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.

Cool and Invert:

  • Let the cupcakes cool in the pan for 5 minutes, then carefully invert them onto a wire rack to cool completely. If any pineapple pieces stick to the pan, gently place them back on the cupcakes.


  • Serve the pineapple upside-down cupcakes at room temperature or slightly warmed.

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