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+ servings
A batch of pineapple upside down cupcakes topped with whipped cream and cherries

Pineapple Upside Down Cupcakes

Course Dessert
Cuisine American
Pineapple upside down cupcake bring the traditional taste you know and love into fun bite size servings.
Prep Time 20 minutes
Cook Time 20 minutes
Total Time 40 minutes
Servings 24 cupcakes

Equipment

  • 1 Cupcake Pan

Ingredients

  • 1/2 cup melted butter salted or unsalted
  • 1 1/2 cups light brown sugar
  • 24 maraschino cherries
  • 20 ounces can crushed pineapple drained
  • 15.25 ounce box pineapple cake mix* any box between 15-18 ounces will work
  • 1 1/3 cups pineapple juice
  • 1/3 cups canola oil
  • 3 eggs
  • optional toppings such as powdered sugar, additional cherries, and/or whipped cream, as desired

Instructions

  • Preheat oven to 375 degrees F. Prepare cupcake pan by spraying with non-stick cooking spray.
  • Spoon approximately 1 teaspoon of melted butter into the bottom of the wells of the cupcake pan. To the melted butter, add 1 tablespoon of brown sugar to each well in the pan. Place one maraschino cherry on top of the brown sugar in each well. Gently press into the brown sugar and butter mixture. On top of that, add a tablespoon of crushed pineapple to each well, and then gently press down on the mixture, to compact it in each well, with the back of a spoon. Set aside.
  • In a large bowl, combine cake mix, pineapple juice, oil and egg, and beat with an electric mixer on low speed for approximately 2 minutes.
  • Scoop or pour batter into each of the muffin cups, on top of the prepared fillings. Fill to the top of the well, but do not overfill.
  • Bake for approximately 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. Remove from oven and allow to cool for 10 minutes.
  • After cooling for 10 minutes, gently invert pan, turning cupcakes out. This can be done onto a cooling rack, silicone sheet, parchment paper or a sheet pan. A sheet pan is easiest as you can put it directly onto the cupcake pan, making it easy to invert.

Notes

*Pineapple Cake Mix - If you can't find pineapple cake mix, you can always use a yellow cake mix. If desired you could add some pineapple extract to it, but the pineapple juice will help give it a pineapple flavor, just not as intense as a pineapple cake mix would. 
Standard pineapple cake mixes can range in size from 15-18 ounces. Any size in there will work fine.

Nutrition

Calories: 218kcal | Carbohydrates: 36g | Protein: 2g | Fat: 8g | Saturated Fat: 3g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 3g | Trans Fat: 0.2g | Cholesterol: 31mg | Sodium: 168mg | Potassium: 86mg | Fiber: 1g | Sugar: 28g | Vitamin A: 163IU | Vitamin C: 4mg | Calcium: 63mg | Iron: 1mg
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