This Homemade Pineapple Upside-Down Cake features a caramelized pineapple topping and an incredibly buttery, moist cake. 

A finished pineapple upside down cake resting on a plate with a jar of cherries in the background.

It’s been one of my goals this year to update and re-share some classic recipes for you to have on hand for when you need them. Today’s recipe is one I’ve always loved and I think you’ll love too – this easy pineapple upside-down cake.

One of the things that I love about this recipe is that it’s made completely from scratch. But don’t worry, it’s still incredibly easy to make! You can make the topping in the microwave and use canned pineapple slices and maraschino cherries.

The cake batter is also incredibly simple to throw together and uses everyday basic ingredients. It’s so incredibly buttery and moist, it beats anything you can make using a box mix. I think this cake could even convert someone who thinks they don’t like pineapple upside-down cake into loving it.

A round cake pan lined with pineapple slices, cherries, and the caramelized sugar topping.

How To Make Pineapple Upside-Down Cake

There are two components to making this pineapple upside-down cake, the topping and the cake batter. Let’s discuss how to prepare each one!

How To Make The Topping

To make the topping for this cake you’ll melt some butter, then stir in some brown sugar, and spread it around into a 9-inch cake pan. If you want to make this step a bit easier, feel free to use the microwave to melt your butter.

Since I prefer to keep this recipe simple I use canned pineapple slices and a small jar of maraschino cherries. Just be sure to reserve the pineapple juice from the can because you’ll be using some of it in the cake, which I will explain later.

You can arrange the pineapple slices and maraschino cherries however you like in the pan. A 20-ounce can of sliced pineapple will usually have 10 slices, so I like to arrange seven on the bottom of the pan and slice the other 3 in half and place them along the sides. Then, place the cherries where ever they will fit. Once the topping is ready, set it aside and prepare the cake batter. 

A glass mixing bowl holding cake batter that has been mixed up.

How To Make The Cake

To make the cake, you will start out by whisking together your dry ingredients – some all-purpose flour, baking powder, and salt. When measuring your flour it’s important to use the spoon and level method, otherwise, you can end up with a dense cake. Once the dry ingredients are well combined, set them aside and mix up the wet ingredients.

For the wet ingredients, you’ll start by creaming together some unsalted butter, granulated sugar, and brown sugar for 4 to 5 minutes or until the mixture is light in color and fluffy. This step is crucial because it incorporates more air into your cake batter which results in a lighter, fluffier cake.

Next, mix in your eggs one at a time until they’re fully incorporated into the creamed butter and sugar. Then, mix in the pure vanilla extract and sour cream. At this point your batter may look a little bit curdled, but this is okay! 

Once the wet ingredients are well combined, whisk together the remaining milk and pineapple juice. You can just use 1/2 cup of milk in this step, but I found incorporating a little bit of pineapple juice will infuse the cake with more pineapple flavor. Then, just alternate mixing in the dry ingredients with the milk + pineapple mixture. 

A pineapple upside down cake on a plate with one slice taken out to show the texture of the cake.

Carefully pour the batter over the topping in your cake pan and spread it around into one even layer. The cake will take about 45 to 55 minutes in the oven, you will know it’s done when a toothpick inserted into the center comes out clean. I recommend letting it cool slightly, then flipping the cake out of the pan. 

FAQ’s

Can you freeze pineapple upside-down cake?

Yes, you can freeze it! You can either wrap individual slices or the whole cake tightly with plastic wrap, store it in a freezer bag or container, and freeze for up to 3 months. I recommend thawing it overnight in the refrigerator and letting it come to room temperature before serving.

How do you store it?

You may store this cake in an airtight container at room temperature for 2 to 3 days. While it’s not necessary to refrigerate this cake, I do recommend storing it in the refrigerator if you need to store it 1 to 2 days longer. 

Can I use fresh pineapple?

Yes, it’s fine to use fresh pineapple in this cake. You can juice the pineapple as well to get 1/4 cup of pineapple juice or simply replace the pineapple juice with 1/4 cup of milk.

When do you flip the cake?

Once the cake comes out of the oven, let it cool for 10 minutes in the pan, then flip it and remove it from the pan.

A single piece of cake on a plate with a bite taken out of it.

Baking Tips

  • Make sure all of your ingredients, including the butter, eggs, sour cream, and milk, are all at room temperature before getting started. This will help ensure that they mix together properly.
  • When measuring your flour, make sure to spoon it into your measuring cup and level it off with the back of a knife.
  • If the cake begins to brown too much in the oven before it’s done baking, loosely cover it with aluminum foil until it’s fully baked.
  • Want to make a mini version? Try my mini pineapple-upside down cakes.

More Cake Recipes To Try!

Video Tutorial

A whole pineapple upside down cake on a plate with a jar of cherries in the background.

Pineapple Upside-Down Cake

4.93 from 27 ratings
Prep Time: 30 minutes
Cook Time: 50 minutes
Total Time: 1 hour 20 minutes
This homemade Pineapple Upside-Down Cake features a caramelized pineapple topping and an incredibly buttery, moist cake.
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Ingredients

Servings: 8 slices

For the topping:

  • ¼ cup (60 grams) unsalted butter melted
  • ½ cup (100 grams) light brown sugar packed
  • 1 20-ounce can pineapple slices reserve juice for the cake
  • 20 maraschino cherries

For the cake:

  • 1 and ½ cups 190 grams all-purpose flour, spooned & leveled
  • 1 and 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup (115 grams) unsalted butter softened to room temperature
  • 1/2 cup (100 grams) granulated sugar
  • 1/4 cup (50 grams) brown sugar
  • 2 large eggs at room temperature
  • 1 teaspoon pure vanilla extract
  • 1/4 cup (60 grams) sour cream at room temperature
  • 1/4 cup (60 ml) whole milk at room temperature
  • 1/4 cup (60 ml) pineapple juice

Instructions
 

  • Preheat the oven to 350°F (177°C). Spray a 9-inch cake pan with nonstick cooking spray and set aside.

To make the topping:

  • In a small mixing bowl, whisk together the melted butter and brown sugar until fully combined. Pour into the prepared cake pan and spread it around into one even layer. Arrange the pineapple slices on top, cut any extra slices in half and place along the sides of the pan, then place the maraschino cherries in and around the pineapple slices. Set aside.

To make the cake:

  • In a large mixing bowl, whisk together the flour, baking powder, and salt. Set aside.
  • In the bowl of a stand mixer fitted with the paddle attachment, or in a large mixing bowl using a handheld mixer, cream the butter, granulated sugar, and brown sugar together until light and fluffy (about 4-5 minutes). Mix in the eggs, one at a time, until fully combined. Then, mix in the vanilla extract and sour cream until well combined, making sure to stop and scrape down the sides of the bowl as needed.
  • Whisk together the pineapple juice and milk.
  • With the mixer on low speed, mix in the dry ingredients in three additions, alternating with the milk and pineapple juice.
  • Pour the batter into the cake pan on top of the pineapple slices and cherries and spread it around into one even layer.
  • Bake for 45 to 55 minutes or until a wooden toothpick inserted into the center of the cake comes out clean. If needed, tent with aluminum foil for the last 10 to 15 minutes of baking to prevent excess browning.
  • Remove the cake from the oven and allow to cool for about 10 minutes in the pan, then invert onto a wire rack and remove from the pan to finish cooling.

Notes

Store cake in an airtight container at room temperature for 2 to 3 days. While it's not necessary to refrigerate this cake, I do recommend storing it in the refrigerator if you need to store it 1 to 2 days longer.
Freezing Instructions: Wrap individual slices or the whole cake tightly with plastic wrap, store it in a freezer bag or container, and freeze for up to 3 months. Thaw overnight in the refrigerator and bring to room temperature before serving.
Milk: I prefer to use whole milk for a richer taste and texture. However, you may replace it with 2%, 1%, skim, or almond milk.
Sour Cream: Full-fat sour cream is best, but low-fat is okay too. You may also replace the sour cream with an equal amount of plain Greek yogurt.
Pineapple Juice: If you don't have any pineapple juice on hand, you can replace it with an equal amount of milk.
 
Cuisine: American
Course: Dessert
Author: Danielle
Did you make this recipe?Mention @livewellbakeoften on Instagram or tag #livewellbakeoften.