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A pineapple upside down cupcake with whipped cream and a cherry on top, a fork bite taken out of the front of it.
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Pineapple Upside Down Cupcakes

These fun and personal-sized Pineapple Upside Down Cupcakes are a mini version of your favorite cake in cupcake form! Buttery pineapple cake mix, sweet brown sugar drizzle, pineapple pieces, and finished with a cherry on top.
Course Dessert
Cuisine American
Keyword pineapple upside down cupcakes
Prep Time 10 minutes
Cook Time 25 minutes
Total Time 35 minutes
Servings 24
Calories 240kcal
Author Jessica - Together as Family

Equipment

Ingredients

  • 2 cans (20 oz each) crushed pineapple (drained, juice reserved)
  • 1 box (15.25 oz) yellow cake mix
  • 3 large eggs
  • 1/2 cup vegetable oil
  • 10 tablespoons butter melted
  • 1 cup packed light brown sugar
  • 1 jar (10 oz) maraschino cherries
  • whipped cream (optional garnish)

Instructions

  • Preheat the oven to 350℉. Prepare two 12-cup standard muffin/cupcake tins by spraying each of the muffin cups with nonstick cooking spray. Set aside. 
  • Drain the canned crushed pineapple making sure to place a bowl below the strainer to catch the liquid. Reserve 1 cup of the strained pineapple juice for the cake batter. Set the pineapple juice and drained crushed pineapple aside.
    2 cans (20 oz each) crushed pineapple
  • In a large bowl, add the yellow cake mix, 1 cup reserved pineapple juice, large eggs, and vegetable oil. Using an electric mixer or stand mixer, beat the ingredients on low speed until combined, then increase the speed to medium for 2 minutes. 
    1 box (15.25 oz) yellow cake mix, 3 large eggs, 1/2 cup vegetable oil
  • In a small bowl, combine the melted butter and light brown sugar. 
    10 tablespoons butter, 1 cup packed light brown sugar
  • Assemble Each Pineapple Upside Down Cupcake :
    - Add 1 whole maraschino cherry to the center of each muffin cup.
    - Then spoon 1 teaspoon of the brown sugar butter mixture over top the cherry, ensuring it covers the bottom of the muffin cup.
    - Next, spoon 1 tablespoon of the drained crushed pineapple (set aside from earlier) over the brown sugar mixture avoiding the top of the cherry.
    - Gently spoon or pipe the yellow cake batter over each muffin cup filling to about 1/4-inch from the top of the muffin cup.
    1 jar (10 oz) maraschino cherries
  • Place the cupcakes in the oven and bake for 20-25 minutes or until a toothpick inserted into the cake part comes out clean. 
  • Cool for 5 minutes on a wire cooling rack, then gently remove the cupcakes by inverting the pan using the cooling rack as a backstop. Garnish each one with fresh whipped cream (homemade, Cool Whip, or store-bought spray cream) and extra cherry if wanted.
    whipped cream
  • Serve the pineapple upside down cakes warm. Enjoy!

Notes

  • Use plenty of cooking spray in each cupcake tin to ensure the cupcakes come out smoothly. 
  • Leave enough space in each muffin cup for the cake batter to expand. Be careful not to overfill or else the cake batter will spill over. Leave about 1/4-inch of space between the top of the cake batter and the top of the muffin cup. 
  • When draining the crushed pineapple make sure you place a bowl underneath the strainer to catch the pineapple juice! You will need it for the yellow cake mix mixture to give it that fresh pineapple flavor.
  • Use a yellow cake mix, golden butter cake mix, or buttery yellow cake mix. 

Nutrition

Calories: 240kcal | Carbohydrates: 36g | Protein: 2g | Fat: 10g | Saturated Fat: 4g | Polyunsaturated Fat: 3g | Monounsaturated Fat: 3g | Trans Fat: 0.3g | Cholesterol: 36mg | Sodium: 181mg | Potassium: 92mg | Fiber: 1g | Sugar: 28g | Vitamin A: 208IU | Vitamin C: 4mg | Calcium: 64mg | Iron: 1mg