Pineapple Upside Down Cupcakes

These Pineapple Upside down Cupcakes have a tender yellow cupcake that is baked with a pineapple ring and an easy caramel sauce. The cupcake is turned upside down to serve, making the perfect single sized cake.

Course Dessert

Cuisine American

Prep Time 15

Cook Time 25

Total Time 40

Servings servings

Calories 610kcal

Author Deborah Harroun

Ingredients

2 1/2 cup all-purpose flour
1 teaspoon baking powder
1/2 teaspoon baking soda
1/2 teaspoon salt
2 large eggs
2 large egg yolks
2 cups sugar
1 cup neutral flavored oil such as vegetable or canola
2 teaspoons vanilla extract
1 cup sour cream
6 tablespoons unsalted butter
2 tablespoons light corn syrup
1 cup packed light brown sugar
12 pineapple slices*
12 maraschino cherries stems removed
Fresh whipped cream for serving, optional

Instructions

Preheat the oven to 350ºF. Line the bottom of 12 jumbo muffin tins** with parchment paper or wax paper. Spray the tins with nonstick cooking spray.
In a bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.
2 1/2 cup all-purpose flour, 1 teaspoon baking powder, 1/2 teaspoon baking soda, 1/2 teaspoon salt
In the bowl of a stand mixer, or in another large bowl, beat the eggs, egg yolks, and the sugar together until light and fluffy, 2-3 minutes. Scrape down the sides of the bowl, then add in the oil and the vanilla and continue to beat until combined. Add the sour cream and and mix until no streaks of white remain. Add the flour mixture and mix just until combined.
2 large eggs, 2 large egg yolks, 2 cups sugar, 1 cup neutral flavored oil, 2 teaspoons vanilla extract, 1 cup sour cream
In a saucepan, melt the butter with the corn syrup and the brown sugar. Cook over medium heat, stirring often, until the mixture is smooth and the sugar is dissolved. Remove from the heat.
6 tablespoons unsalted butter, 2 tablespoons light corn syrup, 1 cup packed light brown sugar
Carefully divide the caramel mixture between the 12 cups. Be careful not to touch it, as it is very hot. Each cup will need a heaping tablespoon of the caramel. (I used a small spring loaded cookie scoop.) Place a pineapple ring on top of the caramel in each cup, then place a cherry in the center of each pineapple.
12 pineapple slices*, 12 maraschino cherries
Divide the cupcake batter evenly between the 12 cups. The batter should nearly reach the top of the cup.
Bake in the preheated oven until a toothpick inserted in the middle of the cupcake comes out clean or with just a few moist crumbs. When testing, make sure you don’t push the toothpick all the way down to the pineapple.
When done, remove from the oven and let the cupcakes sit for 5 minutes. Carefully run a knife around the edges of the cupcakes, then carefully flip the pan over onto a serving platter to remove the cupcakes.
Serve with freshly whipped cream, if desired.
Fresh whipped cream

Notes

slightly adapted from cupcakes!

*If using canned pineapple, you will need 1 20-oz can and 1 8-oz can of pineapple in its own juice. You can also use fresh pineapple. If using fresh pineapple, try to dry it off before using as it usually has more moisture.

**Most jumbo muffin tins only have 6 cups. If you only have one pan, you’ll have to bake the cupcakes in 2 batches. This will work best if baked all at the same time, though.

Nutrition information provided as an estimate only. Various brands and products can change the counts. Any nutritional information should be used as a general guide. Nutritional information does not include whipped cream.

Nutrition