Pineapple Upside Down Cake

This pineapple upside down cake has a tender, velvety crumb with a buttery, vanilla flavor, and is topped with pretty pineapple rings and maraschino cherries.

Course Dessert

Cuisine American

Keyword cast-iron skillet cakes, pineapple cake recipes, upside down cakes

Prep Time 20

Cook Time 35

Total Time 55

Servings slices

Calories 786kcal

Author Kathleen

Ingredients

Topping:

1 cup brown sugar, firmly packed
6 tablespoons butter
1/2 teaspoon vanilla extract
1 (20-ounce) can pineapple slices, drained
15-20 maraschino cherries, stems removed

Cake:

1 cup cake flour
1 cup all-purpose flour
1 teaspoon baking powder
1 teaspoon baking soda
1/4 teaspoon salt
1/2 cup butter, softened
1 cup sugar
2 large eggs at room temperature
1 cup buttermilk, well shaken, at room temperature
2 teaspoons vanilla extract

US Customary - Metric

Instructions

Make Topping:

In a 9-inch cast iron pan set over medium heat, melt 6 tablespoons of butter. Add 1 cup of the brown sugar and whisk for about 2 minutes, or until the sugar dissolves and the syrup boils and bubbles. Add vanilla (1/2 teaspoon) after removing it from the heat.
Pat the pineapple (1 can) very dry between several thicknesses of paper towel and carefully arrange it evenly on the sugar mixture. (Remember skillet is still hot!)
Add the cherries (15-20) to the inside of the pineapple rings then wherever there’s a gap.
Adjust oven rack to center position. Preheat the oven to 375°F (191°C).

Make Cake:

In a medium, mixing bowl, whisk together both flours (1 cup cake flour + 1 cup all-purpose flour), baking powder (1 teaspoon), baking soda (1 teaspoon), and salt (1/4 teaspoon); set aside.
In a large mixing bowl, using a hand-held electric mixer, cream together butter (1/2 cup) and sugar (1 cup) on medium speed until light and fluffy, about 3 minutes.
Add eggs (2) one at a time, beating just until the yolk disappears.
Add the flour mixture and buttermilk (1 cup) alternately, beginning and ending with the flour mixture, with the mixer on low, beating just until combined. Stir in the vanilla (2 teaspoons).
Gently spoon the batter evenly over the pineapple slices. Bake in preheated oven until golden brown and a toothpick inserted into the center of the cake comes out clean, 35 to 40 minutes.
Cool the cake in the skillet on a wire rack for 4 minutes only.
Remove the cake from the oven and cool on a wire rack for 4 minutes. Run a butter knife around the edge of the skillet and, wearing oven mitts and working quickly, invert the cake onto a cake plate, keeping the plate and skillet firmly pressed together.
Carefully lift the skillet off the cake and replace any fruit stuck to the bottom of the skillet, if necessary. Serve warm or at room temperature.

Notes

Cast Iron Skillet: The cast iron skillet is perfect to make this type of cake. This recipe starts on the stovetop and then is baked in the oven. Cast iron absorbs heat and holds it, so it’s perfect when you use both types of cooking and baking sources.
Cake Pan: Yes, you can this cake in a 9-inch cake pan. Make the brown sugar topping in a saucepan, following the instructions above
Pineapple Chunks: If you’d prefer, or simply happen to have a can of pineapple chunks or tidbits, feel free to use them instead. Follow the instructions for drying the pineapple rings and do so for the chunks.
Dry The Fruit: drain the pineapples very well.

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