Pineapple Upside-Down Cupcakes

Prep: 20 mins

Cook: 35 mins

Total: 55 mins

Servings: 12 servings

Yield: 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 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.

   

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. 

   

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. 

   

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. 

   

6. In a large bowl, beat eggs and sugar until thickened and lemon colored. 

   

7. Beat in oil, sour cream, vanilla extract, and rum extract until smooth. 

   

8. In another large bowl, combine flour, baking powder, baking soda, and salt. 

   

9. Add flour mixture to egg mixture and mix well.

   

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. 

    

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.)

    

12. Enjoy on their own, or serve with a dollop of whipped cream or a scoop of vanilla ice cream.