Pineapple Upside Down Cake

By Laurel Perry

Published May 13, 2024

This old-fashioned pineapple upside down cake recipe consists of a moist fluffy cake topped with baked-in rings of tart pineapple and sweet maraschino cherries. I love how simple this cake is to make. It was such a fun party trick the first time I made it to invert the cake in front of everyone for a show-stopping surprise.

A pineapple upside down cake on a plate. - 5

I’ve always wanted to make a pineapple upside down cake, but I was so intimidated the first time I tried. I’ve heard horror stories about the cake sticking to the pan and coming out a total mess! I was so impressed that mine turned out great on the first try, and I’m confident that yours will too– it’s all in the timing!

What’s in This Pineapple Upside Down Cake Recipe?

Butter: Unsalted butter prevents the cake from sticking to the tin and helps make the cake tender and moist.
Sugar: Brown sugar sweetens the topping, while granulated sugar sweetens the cake.
Pineapple: Canned pineapple rings make a beautiful topping, and the reserved juices from the can add moisture and flavor to the cake.
Cherries: Maraschino cherries add a pop of color and sweetness to the topping.
Flour: All-purpose flour gives the cake structure.
Baking Powder: Helps the cake rise in the oven.
Eggs: Add richness and additional moisture to the cake.
Sour Cream: Our favorite secret ingredient that makes this cake so moist and tender.
Vanilla: Pure vanilla extract enhances the sweetness of the cake.

A slice of pineapple upside down cake on a plate. - 6

Tips for Success

Measure the flour using the spoon-and-level method to avoid a dense, dry cake.
Take care not to overmix the batter, which overdevelops gluten and leads to a dense, gummy cake.
If the batter becomes too runny due to warm ingredients, refrigerate it for a short time to firm it up before pouring over the pineapple layer.
Check the cake for doneness by inserting a toothpick into the center. It should come out with a few moist crumbs, but not wet. Overbaking can result in a dry cake.
Do not try to invert the cake before it has cooled for 15-20 minutes. This cooking time helps the cake release from the pan

How to Store and Reheat

Store leftover pineapple upside down cake wrapped well in plastic wrap at room temperature for up to 2 days or in the refrigerator for up to 4 days. Enjoy at room temperature or gently warmed in the microwave.

Freeze pineapple upside down cake whole or cut into individual slices tightly wrapped in 2 layers of plastic wrap and 1 layer of aluminum foil for up to 3 months. Let thaw overnight in the refrigerator before enjoying.

A slice of pineapple upside down cake on a plate. - 7

Ingredients1x2x3x

For the Topping

▢ ⅓ cup unsalted butter 75 grams, melted (⅔ stick)
▢ ½ cup brown sugar 107 grams
▢ 20 ounces sliced pineapple 567 grams, drained and juice reserved (1 large can)
▢ 13 maraschino cherries stems removed

For the Cake

▢ 1½ cups all-purpose flour 195 grams
▢ 1½ teaspoons baking powder 6 grams
▢ ¼ teaspoon kosher salt
▢ ½ cup unsalted butter 113 grams, room temperature (1 stick)
▢ ¾ cup granulated sugar 150 grams
▢ 2 large eggs 100 grams, room temperature
▢ ¼ cup sour cream 57 grams, room temperature
▢ ¼ cup reserved pineapple juice 57 grams, from the can above
▢ 1 teaspoon pure vanilla extract 4 grams

Video

Instructions

Preheat oven to 350°F.
For the topping, pour the melted butter into a 9-inch round cake pan. Use a pastry brush or folded paper towel to spread it around into one even layer. Sprinkle the brown sugar evenly over the melted butter. ⅓ cup unsalted butter, ½ cup brown sugar
Arrange the pineapple slices over the butter/sugar mixture. Place a maraschino cherry in the middle of each pineapple ring. 20 ounces sliced pineapple, 13 maraschino cherries
In a large bowl, whisk the flour, baking powder, and salt together. 1½ cups all-purpose flour, 1½ teaspoons baking powder, ¼ teaspoon kosher salt
In the bowl of a stand mixer fitted with the paddle attachment, beat the butter and granulated sugar together until light and fluffy, about 2 minutes. ½ cup unsalted butter, ¾ cup granulated sugar
Add in the eggs one at a time, beating each egg until combined. Scrape down the sides as needed. 2 large eggs
Mix in the sour cream, pineapple juice, and vanilla extract, scraping down the bowl as needed. ¼ cup sour cream, ¼ cup reserved pineapple juice, 1 teaspoon pure vanilla extract
Add in the dry ingredients and mix until just combined.
Gently pour the batter into the pan and spread it into an even layer.
Bake for 30 minutes, then cover loosely with aluminum foil and bake for another 15 minutes.
Cool the cake on a wire rack for 15-20 minutes before inverting onto your serving plate.

Equipment

Kitchen Scale (optional)
9-inch Round Cake Pan
Stand Mixer

Becky’s Tips

You can use whole milk in place of the sour cream and/or pineapple juice.
This cake is best enjoyed warm. The topping will be gooey, and the flavors will be at their peak.

Nutrition information is automatically calculated, so should only be used as an approximation.

How to Make Pineapple Upside Down Cake Step by Step

Prep the Pan: Preheat the oven to 350°F. Pour ⅓ cup of melted unsalted butter into a 9-inch round cake pan. Use a pastry brush or folded paper towel to spread it around into one even layer. Sprinkle ½ cup of brown sugar evenly over the melted butter.

A dish with brown sugar and cinnamon in it. - 8

Make the Topping: Arrange the pineapple slices over the butter/sugar mixture. Place a maraschino cherry in the middle of each pineapple ring.

Pineapples in a pan with cherries on top. - 9

Whisk the Dry: In a large bowl, whisk 1½ cups of all-purpose flour, 1½ teaspoons of baking powder, and ¼ teaspoon of kosher salt together.

Flour in a glass bowl on a marble table. - 10

Cream the Butter and Sugar: In the bowl of a stand mixer fitted with the paddle attachment, beat ½ cup of unsalted butter and ¾ cup of granulated sugar together until light and fluffy, about 2 minutes.

Add the Wet: Add in 2 large eggs one at a time, beating each egg until combined. Scrape down the sides as needed. Mix in ¼ cup of sour cream, ¼ cup of reserved pineapple juice, and 1 teaspoon of pure vanilla extract, scraping down the bowl as needed.

Mix the Dry and Wet: Add in the dry ingredients and mix until just combined.

Spread the Batter: Gently pour the batter into the pan and spread it into an even layer.

Bake and Cool: Bake for 30 minutes, then cover loosely with aluminum foil and bake for another 15 minutes. Cool the cake on a wire rack for 15-20 minutes before inverting it onto your serving plate.

A pineapple upside down cake with cherries on top. - 15

Pineapple was a very trendy ingredient in the mid-1920s after a successful ad campaign from the Dole Pineapple Company. The reveal from flipping the cake out of the pan made it a show-stopping dessert for elegant dinner parties.

This cake fares best in a nonstick 9-inch cake pan. The nonstick coating combined with the melted butter helps prevent the pineapple topping from sticking to the pan.

When properly made, this cake does not need parchment paper. But if it’s your first attempt and you’re feeling nervous, you can absolutely use it.

Make sure to drain the pineapple juice from the canned pineapple before lining the pan. You can also pat the pineapple slices and cherries dry with a paper towel to remove excess moisture.

In order for your cake to come out cleanly, you must be patient and wait the full 15-20 minutes before flipping it. It needs to cool slightly in order for the topping to firm up enough to slide cleanly out of the pan. You can also run a butter knife around the edges of the pan before flipping to release any stuck bits.

You can leave this cake out for up to 2 days. However, keep in mind that moist cakes tend to mold quickly, especially in hot or humid climates, so you may want to refrigerate it immediately in the warmer months.

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A pineapple upside down cake on a plate. - 16

Pineapple Upside Down Cake Recipe

Equipment

Kitchen Scale (optional)
9-inch Round Cake Pan
Stand Mixer