Best Pineapple Upside Down Cake

This easy Pineapple Upside Down Cake bakes up perfectly every time with sweet caramelized pineapple and maraschino cherries on a moist and buttery cake with slightly crispy edges from the cast iron skillet.

Course Dessert

Cuisine American

Keyword how to make pineaplple upside down cake, pineapple cake, pineapple upside down cake recipe, upside down pineapple cake

Prep Time 20

Cook Time 40

Servings servings

Calories 349kcal

Author Beth Pierce

Ingredients

Cake
1 ½ cups cake flour
1 teaspoon baking powder
¼ teaspoon baking soda
¼ teaspoon salt
½ cup unsalted butter softened to room temperature
¾ cup granulated sugar
2 large eggs room temperature
1 teaspoon vanilla extract
2 tablespoons milk
½ cup pineapple juice from the can of pineapple

Topping

¼ cup unsalted butter
⅔ cup packed light brown sugar
1 20-ounce can pineapple rings (reserve ½ cup pineapple juice)
19 maraschino cherries

Instructions

Preheat the oven to 350 degrees. Grease a 10 or 11-inch cast iron skillet with vegetable shortening.
In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set it aside for a few minutes.
Using a stand mixer or a handheld mixer on medium speed, cream the butter and sugar together for about 2 minutes. Reduce the speed to low and add the eggs one at a time, mixing just until incorporated. Mix in the vanilla extract.
Add the flour mixture in several intervals alternating with the pineapple juice and the milk. Mix just until combined scraping down the bowl and beater as needed.
Meanwhile, melt the butter in a 10 or 11-inch cast iron skillet in the oven. It only takes about 5 minutes, so keep an eye on it. Sprinkle in the brown sugar as evenly as possible. Top with a single layer of pineapple slices and fill in the spaces with maraschino cherries.
Gently pour the cake batter over the top and bake the cake in the oven for 30 minutes. Then tent the pan loosely with aluminum foil. Bake for another 10-15 minutes until a toothpick inserted in the center comes out clean.
Cool the cake in the pan for 10 minutes. Then carefully invert onto a serving plate. Let the cake cool for 2-3 hours before slicing and serving.

Notes

If you do not have a cast iron skillet, you can make this recipe in a 9 or 10-inch cake pan as long as it is 2 inches deep.
You can use all-purpose flour, but cake flour produces a more tender crumb.
Get the canned pineapple in juice, not the one in syrup.
Arrange the pineapple slices and pitted maraschino cherries as pictured above.
Blot and dry the maraschino cherries with paper towels to keep them from bleeding through the cake.
Carefully invert the cake onto a serving plate after 10 minutes. This is the perfect time to flip it, so stick with it. If you go too soon, the cake might fall apart, and if you wait much longer, it will stick.
Cool the cake for 2-3 hours before slicing it with a sharp knife to ensure the slices do not fall apart.
Cover and store this cake in the refrigerator for up to 3 days or freeze for up to 3 months.

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