With its caramelized pineapple and brown sugar topping, maraschino cherries, and moist vanilla cake, it’s hard to resist the retro-classic, Pineapple Upside Down Cake. This easy dessert is perfect for any occasion or gathering, but it’s so good you may just make it for no reason at all!
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A favorite retro dessert
Whenever I take a bite of Pineapple Upside Down Cake, I’m reminded of a time when things were a little simpler. Before cell phones, the internet, and other distractions existed. My mom would make this 1920s-style inverted dessert often when I was a kid, and I always loved it!
The sweet caramelized brown sugar, pineapple, and cherry topping is the perfect complement to the moist and delicious pineapple-infused vanilla cake.
Much like pound cake, this is one of those desserts that’s perfect for when “company is coming over”, but I do make it more often than that…just because.
Recipe Ingredients
All ingredients for this recipe are shown in the pic below and special notes are made in this bulleted list to assist you.
- Pineapple. As much as I love fresh fruit for many recipes such as my lemon blueberry ricotta cake and peach blueberry crisp, pineapple upside-down cake calls for canned pineapple rings for the topping, and juice for the cake.
- Cherries. Any variety of maraschino cherries or amarena cherries works for this recipe.
- Sugar. Light or dark brown sugar is used for the topping, while granulated sugar is used for the cake.
- Flour. I’m using cake flour as it yields a lighter, fluffier pineapple upside down cake, but you can use all-purpose flour if that’s what you have.
See the recipe card for full information on ingredients and quantities.
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How to make easy pineapple upside down cake
Each number corresponds to the numbered written steps below.
- Pour the melted butter into a deep 9-inch pie dish and grease the sides with the butter.
- Sprinkle the brown sugar all over the butter, then lay the pineapple slices into the plate in a uniform pattern without overlapping. You may need to cut the remaining pieces to fill any empty spots around the edges. Place a cherry into each pineapple ring hole, including any half slices.
- In a small bowl, combine the cake flour, baking powder, and salt.
- In a large bowl, use a hand mixer to cream the butter and sugar.
- Add the eggs, one at a time, then add the vanilla and pineapple juice.
- Fold a portion of the dry ingredients and milk into the wet until all the milk, wet, and dry ingredients are combined. Be sure not to overmix.
- Pour the cake batter into the pie dish, covering the pineapple and cherries.
- Bake in a 350°F oven for 20 minutes then loosely cover with foil and continue to bake for an additional 25-30 minutes or until a toothpick inserted in the center comes out mostly clean.
- Place the pie dish on a wire rack to cool for 10 minutes, then carefully (use gloves as the dish will still be hot), invert the cake onto a plate.
- Remove the pie plate from the top of the cake. Allow the cake to cool a bit more, then serve and enjoy!
Top tips
- Prepare the pie dish. Be sure to take the time to butter the sides of the pie dish. This step is important to ensure the pineapple upside down cake is easy to remove once flipped.
- Blot the pineapple rings. Blotting the pineapple slices with paper towels will help prevent the pineapple topping from being overly moist and heavy.
- Room temperature ingredients. Starting with room temperature eggs, milk, pineapple juice, and butter will help ensure the cake ingredients blend together better.
More old-school desserts
If you’re looking for more desserts that harken back to a simpler time, give these recipes a try.
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Easy Pineapple Upside Down Cake
Ingredients
For the topping
- 1/4 cup unsalted butter melted
- 1/2 packed cup light or dark brown sugar
- 9 slices canned pineapple rings patted dry to remove excess moisture
- maraschino cherries
For the cake
- 1 1/2 cups cake flour can also use all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/2 teaspoon fine sea salt
- 1/2 cup unsalted butter room temperature
- 3/4 cup granulated sugar
- 2 large eggs room temperature
- 2 teaspoons vanilla extract
- 1/4 cup pineapple juice from can, room temperature
- 1/4 cup milk room temperature
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Instructions
- Preheat oven to 350°F
- Pour the melted butter into a deep 9" pie dish. Grease the plate sides with the butter as well. Sprinkle the brown sugar all over the butter. Place the pineapple slices into the plate in a uniform pattern without overlapping. Cut the remaining pieces to fill the empty spots around the sides of the pie dish. Place a cherry into each pineapple hole including the half slices.
- In a small bowl combine the cake flour, baking powder, and salt.
- In a large bowl, with a hand mixer, cream the butter and sugar. Mix in the eggs, one at a time. Mix in the vanilla and pineapple juice.
- Using a spatula fold a portion of the dry ingredients and milk into the wet ingredients until all of the milk, wet, and dry ingredients are combined. Make sure to not overmix.
- Pour the cake batter into the pie dish. Bake for 20 minutes then loosely cover with foil and continue to bake for an additional 25-30 minutes or until a toothpick pulls out mostly clean.
- Place the pie dish on a wire rack to cool for 10 minutes then carefully (the dish will still be hot) invert/flip the cake onto a plate. Enjoy!
Notes
- Servings. Makes 8 large or 10-12 smaller slices.
- Pineapples. 7 whole rings and pieces of about 2 more rings will be needed. Make sure to pat the pieces dry with paper towels to remove the moisture.
- Flour. Cake flour is recommended for a lighter and fluffier cake, but all-purpose flour will work well too.
- Sticking and flipping. Buttering the pie dish sides and flipping after 10 minutes will ensure the cake won’t stick. The pie dish will still be quite hot after 10 minutes, so make sure to wear gloves.
- Oven. This recipe was written for a conventional oven. For convection ovens, reduce the temperature by 25 degrees and begin checking for doneness at the 75% mark.
- Leftovers. Pineapple upside down cake can be stored covered in the refrigerator for up to 5 days.
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.
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I’m a pineapple upside down cake lover.
I cut extra pineapple rings in half to cover the outside ring of cake.
Also, I fill in the gaps with more cherries.
A true hit with all!
And it also works well with a white cake.
Checking on cooking time – 45 minutes for a one layer cake? Is this correct?
Yes. It’s baked for 20 minutes, then covered with foil for the remaining time until a toothpick comes out clean.
i can honestly say you have the most relateable recipes-very nostalgic-and the ingredients aren’t something that’s are impossible to find-actually are what is in most people’s pantries and refrigerators-tu
We’re happy you feel that way, Lois!
Can o use a Dutch oven instead of the pie dish?
Hi Kerry, it would be very difficult to invert a Dutch oven to get the cake out. We wouldn’t recommend doing that.
Can’t wait to try it looks so easy