Pineapple Upside Down Cupcakes: A Retro Favorite in Mini Form | July 23, 2025

There’s something undeniably charming about classic desserts—and none quite as delightful as the Pineapple Upside Down Cake. But what if you could take that nostalgic treat and turn it into something even more fun, shareable, and irresistibly cute?

Enter: Pineapple Upside Down Cupcakes — all the tropical sweetness and buttery caramel flavor of the original, baked into individual, handheld cakes that are as pretty as they are delicious.

Whether you’re hosting a summer gathering, throwing a retro-themed party, or just want something special for dessert, these cupcakes will steal the show.

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🌞 Why You’ll Love These Cupcakes

• Perfectly Portioned: Individual servings mean no messy slicing.

• Sweet & Tangy: The combination of brown sugar, pineapple, and cherry is a timeless flavor bomb.

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• Beautiful Presentation: Flip them over and you’ve got a glossy pineapple topping with a pop of color from the cherry.

• Quick to Make: Uses simple ingredients, and you can even start with a boxed cake mix for ease.

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🧁 Ingredients

For the Topping:

• ¼ cup unsalted butter (melted)

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• ½ cup packed brown sugar

• 1 can (20 oz) pineapple slices in juice, drained and cut into small pieces or halves

• Maraschino cherries (1 per cupcake)

For the Cupcake Batter (Easy Method):

• 1 box yellow cake mix

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• 3 large eggs

• ½ cup vegetable oil

• 1 cup pineapple juice (from the can)

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👩‍🍳 How to Make Pineapple Upside Down Cupcakes