Pineapple Upside Down Cupcakes

These Pineapple Upside Down Cupcakes bake in a jumbo muffin tin with caramelized pineapple and a cherry on top, a fun, individual twist on the classic cake.

Course Dessert

Cuisine American

Keyword Pineapple Upside Down Cupcakes

Prep Time 15

Cook Time 30

Servings servings

Calories 524kcal

Author Jason Decker

Ingredients

For the cake:

2 ¾ cup cake flour
2 teaspoons baking powder
½ teaspoon fine sea salt
1 cup unsalted butter softened
1 cup granulated sugar
¾ cup light brown sugar packed
4 large eggs room temp
½ cup crushed pineapple
1 tablespoon vanilla extract
¾ cup buttermilk room temp

Instructions

Preheat the oven to 350°F. Spray 12 sections of a jumbo muffin tin with baking cooking spray, set aside.
Add the butter and brown sugar to a small saucepan. Whisk constantly until the sugar is melted 3-5 minutes.
4 tablespoons unsalted butter, ¾ cup light brown sugar
Evenly divide the sauce among the 12 sections of the jumbo muffin tin.
Add a pineapple ring on top of the sauce and place a cherry in the center, repeat with the remaining muffin tin sections. Set aside.
12 pineapple rings, 12 maraschino cherries without stems
In a large bowl, stir together the cake flour, baking powder, and salt, set aside.
2 ¾ cup cake flour, 2 teaspoons baking powder, ½ teaspoon fine sea salt
In the body of a stand mixer with the paddle attachment add the butter, sugar, and brown sugar. Cream together for 3 minutes until light and fluffy.
1 cup unsalted butter, 1 cup granulated sugar, ¾ cup light brown sugar
Add the eggs one at a time, making sure the first one is mixed in before adding the next.
4 large eggs
Stir in the pineapple and vanilla.
½ cup crushed pineapple, 1 tablespoon vanilla extract
Add half of the flour mixture and mix it in.
Add half of the buttermilk and mix it in. Repeat one more time until fully combined. Scrape down the sides as needed.
¾ cup buttermilk
Divide the batter among the 12 sections of the muffin tin. Bake for 20-25 minutes until golden brown and a toothpick inserted into the center comes out clean.
Take the cakes out of the oven and let them sit in the tin on the countertop for 10 minutes. Place a sheet tray on top of the tin and carefully flip the tray over with the muffin tin on top. Wait 5 minutes, then lift the muffin tin off the cakes.
Let cool and serve warm or room temperature.

Notes

Don’t Overfill: Leave a little room at the top of the muffin cups so your batter doesn’t spill over.
Use a Butter Knife: If the cakes won’t budge after flipping, run a butter knife around the edges to loosen them, but be gentle—no one wants a split pineapple ring!
Check for Golden Brown: You’ll know they’re done when the tops (which become the bottoms) are lightly golden brown. A toothpick in the center of the cake should come out clean.
Cool Before Flipping: Let them rest for about 10 minutes. Flipping too soon can cause hot syrup to run everywhere—ouch!
Divide Batter Evenly: If you want each cake the same size, use a measuring cup or scoop so you don’t guess and end up with tall or short ones.
Experiment: This is a classic dessert, but add your flair. Whether it’s fresh pineapple slices or a drizzle of chocolate, it’s your time to shine!

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