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Pineapple upside-down cupcakes adorned with pineapple slices and cherries rest elegantly on a white surface.
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5 from 2 votes

Pineapple Upside Down Cupcakes

Indulge in these easy pineapple upside down cupcakes. Perfectly sweet and wonderfully moist, they're a must-try for your next dessert.
Prep Time15 minutes
Cook Time20 minutes
Total Time35 minutes
Course: Baked Goods, Dessert
Cuisine: American
Keyword: cherry, Cupcakes, pineapple
Servings: 24 cupcakes

Ingredients

Optional Toppings:

Instructions

  • Preheat the oven to 350°F.
  • Generously spray each well of the cupcake pan with cooking spray or use shortening or oil.
  • Cut each slice of pineapple into eight pieces each slice. This is easiest if you cut each slice in half, then cut those halves in half, and then finally each quarter is cut in half.
  • In a mixing bowl, combine the cake mix, eggs, oil, and 1 cup of pineapple juice and mix well to combine.
  • Pour 1 teaspoon of the melted butter into each well of the cupcake pan, then sprinkle 2 teaspoons of the brown sugar into each well. Spread the brown sugar around the bottom of the cupcake well.
  • Press 3 pieces of cut pineapple slices and one stemless cherry in the center. The pineapple pieces might press out slightly.
  • Scoop 3 tablespoons of the batter into each cupcake well until full.
  • Gently tap the cupcake pan on the counter to release any air bubbles.
  • Bake on the center rack for 18 to 20 minutes or until a toothpick inserted in the center comes out clean. If baking 2 trays at a time, rotate the cupcakes 10 minutes into the baking so each one bakes evenly.
  • Let it cool for 10 minutes, then carefully turn them out onto a parchment-lined baking sheet.
  • Allow the cupcakes to cool to room temperature, then serve dusted with powdered sugar or paired with fresh whipped cream.

Notes

Pineapple juice: Dole Sliced pineapple in juice had the full cup of pineapple juice needed for this recipe.  If a different brand is used, you may need to add enough water to the reserved juice to bring the volume to 1 cup.
Cupcake rising: The cupcakes are filled almost to the top of each cupcake, which is natural.  There may be a slight rise during the baking process, but once cooked and resting for 10 minutes out of the oven (before inverting out onto a tray), the cupcakes will re-settle down slightly. 
Topping options: Fresh whipped cream and/or a stemmed maraschino cherry would make a great topping. You could also dust each cupcake with some powdered sugar.

Nutrition

Calories: 170kcal | Carbohydrates: 39g | Protein: 2g | Fat: 1g | Saturated Fat: 1g | Polyunsaturated Fat: 0.2g | Monounsaturated Fat: 0.4g | Trans Fat: 0.1g | Cholesterol: 21mg | Sodium: 174mg | Potassium: 86mg | Fiber: 1g | Sugar: 29g | Vitamin A: 52IU | Vitamin C: 3mg | Calcium: 73mg | Iron: 1mg

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