Pineapple Upside-Down Cupcakes

Pineapple Upside Down Cupcakes

 The Spruce / Kristina Vanni

Prep: 20 mins
Cook: 35 mins
Total: 55 mins
Servings: 12 servings
Yield: 12 cupcakes
Nutrition Facts (per serving)
591 Calories
29g Fat
80g Carbs
5g Protein
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Nutrition Facts
Servings: 12
Amount per serving
Calories 591
% Daily Value*
Total Fat 29g 37%
Saturated Fat 7g 37%
Cholesterol 73mg 24%
Sodium 191mg 8%
Total Carbohydrate 80g 29%
Dietary Fiber 1g 5%
Total Sugars 58g
Protein 5g
Vitamin C 6mg 31%
Calcium 66mg 5%
Iron 2mg 10%
Potassium 180mg 4%
*The % Daily Value (DV) tells you how much a nutrient in a food serving contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.
(Nutrition information is calculated using an ingredient database and should be considered an estimate.)

We all know and love the classic pineapple upside-down cake. It's easy to make, but always gets a wow from your guests when presented at dessert time. This recipe takes everything about the iconic dessert and packages it into portable individually sized cupcakes.

The key to this recipe is using a jumbo-sized muffin tin to make the cupcakes. (Besides, who doesn't want a bigger cupcake?) The jumbo muffin tin is just the right size for a single pineapple ring slice to fit in the bottom. Then, when it's flipped over you have a perfectly shaped pineapple upside-down cupcake. In order to make sure the decadent brown sugar syrup doesn't stick to the bottom of the muffin tin, it's important to line the bottom of each well with a piece of waxed paper or parchment paper. That way, when the cupcakes are inverted, they effortlessly slide out of the pan and the paper can be easily pulled away to reveal the maraschino cherry-filled pineapple ring.

Ingredients

  • 3 (8-ounce) cans pineapple slices in 100% pineapple juice

  • 6 tablespoons unsalted butter, cubed

  • 1 cup firmly packed light brown sugar

  • 12 maraschino cherries, well drained

  • 3 large eggs, room temperature

  • 2 cups sugar

  • 1 cup canola oil

  • 1 cup sour cream

  • 1 teaspoon vanilla extract

  • 1 teaspoon rum extract

  • 2 1/2 cups all-purpose flour

  • 1/2 teaspoon baking powder

  • 1/2 teaspoon baking soda

  • 1/2 teaspoon kosher salt

Steps to Make It

  1. Gather the ingredients.

    Pineapple Upside Down Cupcakes
     The Spruce / Kristina Vanni
  2. Preheat oven to 350 F. Line bottom of 12 greased jumbo muffin cups with parchment paper or waxed paper. Grease paper and set aside.

  3. Drain pineapple slices and reserve 2 tablespoons of juice. 

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  4. In a small saucepan, melt butter over low heat. Stir in brown sugar and reserved pineapple juice. Cook and stir over medium heat until sugar is dissolved. Remove from heat. 

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  5. Spoon 1 tablespoonful of the brown sugar mixture into each muffin cup. Place a pineapple ring into each cup and insert a maraschino cherry into center of each pineapple ring. 

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  6. In a large bowl, beat eggs and sugar until thickened and lemon colored. 

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  7. Beat in oil, sour cream, vanilla extract, and rum extract until smooth. 

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  8. In another large bowl, combine flour, baking powder, baking soda, and salt. 

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  9. Add flour mixture to egg mixture and mix well.

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  10. Fill prepared muffin cups two-thirds full. Bake for 28 to 32 minutes or until a toothpick inserted in the center comes out clean. 

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  11. Cool for 5 minutes before inverting onto wire racks to cool completely. 

    (If using a 6 cup jumbo muffin pan, repeat with remaining ingredients.)

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  12. Enjoy on their own, or serve with a dollop of whipped cream or a scoop of vanilla ice cream.