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Pineapple Upside Down Cake

This retro pineapple upside down cake tastes like a million bucks, and it’s SO easy to make. It’s a moist and tender vanilla cake topped with buttery cherry-filled pineapple rings, bursting with bright fruity flavor!

Easy Pineapple Upside Down Cake Recipe

This pineapple upside-down cake is so flippin’ good! Pun totally intended. It’s a moist, fluffy vanilla cake topped with a layer of gooey caramelized pineapples and dotted with maraschino cherries underneath a buttery brown sugar glaze. It’s easy to make, requiring your basic pantry ingredients, but the flavors and texture are next-level delicious.

This cake is baked – you guessed it – upside down. These retro cakes originated in the 1920s, and this classic recipe is a delicious throwback that’s perfect for the holidays and beyond. 

Why You’ll Love This Upside Down Cake Recipe

  • Classic. Like a strawberry pretzel dessert, a perfect pineapple upside down cake is wonderfully vintage. I don’t know about you, but I love cracking out a good old-timey dessert every now and again.
  • Sweet fruit flavors. This cake recipe is topped with fresh pineapple, juicy maraschino cherries, and a decadent brown sugar glaze. All the flavors come together in a sweet dessert that’s delicious as is and even better topped with whipped cream or ice cream!
  • Easy to make. An upside-down cake might look fancy, but it’s actually so simple to make. This recipe walks you through creating a moist and tender vanilla cake with the signature pineapple topping.
The ingredients for a pineapple upside down cake.

How to Make a Pineapple Upside Down Cake

Just like any retro dessert, this pineapple upside down cake uses simple ingredients. Together, they create a gorgeous cake with a buttery, caramelized top! Below is an overview of how to make this cake. Be sure to scroll to the recipe card for the full ingredient amounts and recipe directions.

Ingredients for the Cake

  • Butter and Brown Sugar: Melted butter caramelizes with brown sugar and pineapple juice to create a rich, sticky glaze over the pineapple topping.
  • Pineapple: You’ll need pineapple juice for the glaze, and fresh pineapple, sliced into rings for topping the cake.
  • Maraschino Cherries: These are sweet preserved cherries in syrup. I don’t recommend substituting maraschino cherries with fresh cherries, as it takes away from the classic flavor of the cake.
  • Flour
  • Baking Powder and Salt
  • Sugar
  • Eggs and Vanilla: Eggs give the cake structure, while vanilla deepens the flavors.


  1. Prepare the brown sugar glaze. Begin by brushing a bit of butter over the inside of a 9” cake pan. Next, you’ll combine a ½ stick of melted butter with brown sugar and pineapple juice and pour the mixture into the bottom of the pan.
  2. Add the pineapple rings. Arrange the pineapple rings over top of the brown sugar mixture, and place a cherry in the middle of each ring. 
  3. Make the cake batter. In a new bowl, whisk together the dry ingredients for the cake. Next, separate the yolks from the egg whites. Beat the egg whites until fluffed, and beat the yolks until smooth. Stir additional pineapple juice, vanilla, and the remaining melted butter into the yolks, then add this into the bowl with the dry ingredients. Finally, fold the egg whites into the batter.
  4. Assemble and bake. Pour the cake batter over the topping in the cake pan, and bake at 400ºF for 30 minutes. The cake will need to cool in the pan for 10 minutes before you can flip it out.
Close-up overhead view of a pineapple upside-down cake on a plate.

How to Flip an Upside Down Cake

The main things to keep in mind when inverting your pineapple upside-down cake are 1) use a plate that’s wider than the cake pan and 2) use oven mitts if your cake pan is still hot when you go to flip it. Here’s how to invert this cake:

  1. Let the cake cool for about 10-15 minutes. This allows the topping and the cake to set up enough to flip. Afterward, run a knife around the edge of the cake to loosen any sticky edges.
  2. Cover the cake pan with an upside-down plate or cake platter – so that the surface of the plate is facing downward against the cake. Then, grip both sides of the plate and cake pan firmly.
  3. Quickly and carefully flip the cake so that the plate is now on the bottom and the cake is facing upwards, pineapple-side-up. Slowly remove the cake pan, and voila! Dig into your cake while it’s still warm.
Slice of pineapple upside down cake on a stoneware plate, next to a fork and a swirl of whipped cream topped with a cherry.

Tips and Recipe Variations

One of the things I love most about these vintage desserts is that they keep the fuss to a minimum. Keep these tips in mind for the perfect pineapple upside-down cake:

  • You can make this recipe with canned pineapple. Canned pineapple rings are the retro choice, and they’re perfect to use if you’re pressed for time. If you’re using canned, I recommend that you drain and pat dry the pineapple slices before adding them to the pan. This way, the top of your cake won’t turn out soggy.
  • Not a fan of maraschino cherries? Try replacing the cherries with pecans or another type of nut.
  • Don’t overmix the cake batter. A pineapple upside down cake is naturally more dense than your average vanilla cake because something needs to hold up all that juicy fruit. However, the cake shouldn’t be overly dense or dry. Make sure that you don’t overmix the batter – this can yield a tough, dry cake.
  • Don’t overbake. Like overmixing, overbaking is another reason your pineapple upside down cake may turn out dry and crumbly. Not all ovens bake the same, too, so make sure that you keep an eye on the cake while it bakes. 
  • To tell if your cake is done baking, insert a toothpick into the center. If the toothpick comes out clean, the cake is done.
  • For another variation made with yogurt, try my pineapple upside down yogurt cake. It’s ultra-moist and made as a sheet cake so it’s great for sharing.
Close-up shot of pineapple upside down cake on a plate next to a swirl of whipped cream topped with a cherry.

Why Is the Top of My Cake Soggy?

While this cake is best served warm when the top is still a little moist, there’s a difference between moist and soggy. If the top of your cake is overly gooey, it could be because you used canned pineapple and didn’t blot away the excess syrup first. Too much moisture in the topping can result in a soggy cake. Also, make sure to serve your cake soon after it’s baked since this is when it has the best texture.

How Do I Keep the Cake From Sticking to the Pan?

The caramelized sugar and butter usually do an excellent job of preventing this cake from sticking. If you notice that the edges of the cake are sticking to the sides of the pan before you flip it, run a knife around the edges to loosen them a bit. If one or two of your pineapple rings get stuck to the bottom of the pan, it’s no biggie. Simply peel them off afterward and place them back on the cake.

A slice of pineapple upside down cake on a stoneware plate garnished with a swirl of whipped cream topped with a cherry.

Serving Suggestions

This cake is perfectly served with a tall glass of milk or a cozy cup of coffee or tea. If you’re looking for some more tasty ways to serve a slice of pineapple upside-down cake, try these ideas:

  • Toppings. Top the cake slices with a swirl of fluffy whipped cream and a maraschino cherry. You can even sprinkle over crushed pecans, walnuts, or chocolate shavings. 
  • Sauces. Drizzle slices of upside down cake with homemade strawberry sauce, or try this boozy chocolate sauce recipe spiked with rum.
  • Ice Cream. Vanilla ice cream is classic, or you can amp up the fruity flavors with a scoop of homemade no churn mango ice cream or my 2-ingredient homemade ice cream with fresh berries. 
  • Brunch. Pineapple upside down cake is a perfect bright addition to a brunch table. Serve it alongside breakfast favorites like buttermilk pancakes and French toast or as a sweet finish to a savory breakfast casserole
Close up of a pineapple upside down cake with a slice missing.

How to Store

  • Fridge. This cake is best when served warm and fresh due to the moisture in the fruit topping. If you have leftovers, wrap them tightly in plastic wrap or place the cake in an airtight container to store in the fridge for up to 3 days. The texture won’t be quite the same, but the flavors of the cake will still be delicious.
  • Freezer. For longer-term storage, double-wrap the cake tightly in plastic wrap and store it in the freezer for up to 2 months. Defrost the cake in the fridge before serving. 


More Easy Cake Recipes

Close-up of a pineapple upside down cake on a plate.

Pineapple Upside Down Cake

Katerina | Diethood
This retro pineapple upside-down cake is a moist, tender vanilla cake topped with buttery pineapple rings and maraschino cherries. It's easy to make, and it's so delicious!
No ratings yet
Servings : 10 Servings
Prep Time 15 minutes
Cook Time 35 minutes
Total Time 50 minutes


For the Topping
  • 12 tablespoons butter, (1-1/2 sticks), melted, divided
  • ¾ cup packed light brown sugar
  • ¾ cup unsweetened pineapple juice, divided
  • 1 fresh pineapple, peeled, cored, and sliced into rings
  • maraschino cherries
For the Cake
  • cups all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
  • ½ cup granulated sugar
  • 3 large eggs, yolks and whites separated
  • ½ teaspoon pure vanilla extract


  • Preheat oven to 400ºF.
For the Topping
  • Melt 8 tablespoons (1 whole stick) of butter in one bowl. In a separate bowl, melt 4 tablespoons of butter (or 1/2 of a stick). Brush some of the melted butter on the inside of a 9-inch cake pan.
  • Mix the 1/2 stick of melted butter (4 tablespoons) with the brown sugar. Whisk in 1/4 cup of the pineapple juice. Pour the brown sugar mixture into the bottom of the prepared cake pan.
  • Arrange the pineapple rings on top of the brown sugar mixture. Place a cherry in the center of each pineapple ring and as many cherries as desired in the gaps between the rings. Set the pan aside.
For the Cake
  • Stir together the flour, salt, white sugar, and baking powder.
  • Separate the eggs, the whites in one bowl, and the yolks in another. Beat the whites until stiff.
  • Beat the egg yolks until smooth and lemony yellow. Stir in the remaining pineapple juice, vanilla, and remaining melted butter. Add this mixture to the flour mixture, then gently fold in the egg whites.
  • Pour the batter over the top of the brown sugar and pineapple rings layer.
  • Bake for 25 to 30 minutes, or until a toothpick inserted in the center of the cake comes out clean.
  • Remove from the oven and let the cake cool in the pan for 10 to 15 minutes before flipping it.
  • Flip the cake by covering the pan tightly with a serving dish and invert so that the pineapple side faces up.
  • Cut and serve.


  • Opt for canned pineapple rings for a quick, vintage touch. Drain and dry them to avoid a soggy cake top.
  • Not keen on maraschino cherries? Substitute with pecans or another nut.
  • Be cautious not to overmix the batter. It should be dense to support the fruit but not tough.
  • Avoid overbaking; ovens vary. Monitor the cake as it cooks.
  • Check doneness by inserting a toothpick in the center. It’s ready if the toothpick emerges clean.
  • To remove the cake from the pan: Cool the cake for 10 to 15 minutes, then use a knife to free any edges. Place a plate or platter face-down atop the cake pan, holding both securely. Invert so the cake sits pineapple-side-up on the plate. Lift off the pan and enjoy.


Serving: 1 Slice | Calories: 364 kcal | Carbohydrates: 55 g | Protein: 4 g | Fat: 15 g | Saturated Fat: 9 g | Cholesterol: 85 mg | Sodium: 262 mg | Potassium: 266 mg | Fiber: 1 g | Sugar: 36 g | Vitamin A: 545 IU | Vitamin C: 45 mg | Calcium: 77 mg | Iron: 1.6 mg | Net Carbs: 54 g

Nutritional info is an estimate and provided as courtesy. Values may vary according to the ingredients and tools used. Please use your preferred nutritional calculator for more detailed info.

Course: Dessert
Cuisine: American
Keyword: easy pineapple upside down cake, pineapple upside down cake
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