Pineapple Upside-Down Cupcakes

Pineapple Upside Down Cupcakes

 The Spruce / Kristina Vanni

  • Total: 55 mins
  • Prep: 20 mins
  • Cook: 35 mins
  • Servings: 12 servings
  • Yields: 12 cupcakes

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 room temperature large eggs
  • 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 salt

Steps to Make It

  1. Gather the ingredients. Preheat the oven to 350 F. Line the bottom of 12 greased jumbo muffin cups with parchment paper or waxed paper. Grease the paper and set aside.

    Pineapple Upside Down Cupcakes
     The Spruce / Kristina Vanni
  2. Drain the pineapple slices and reserve 2 tablespoons of the juice. 

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

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  4. 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 the center of each pineapple ring. 

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

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

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

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

    Pineapple Upside Down Cupcakes
    The Spruce / Kristina Vanni
  9. Fill the 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
  10. 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
  11. Enjoy on its own, or serve with a dollop of whipped cream or a scoop of vanilla ice cream.