Homemade Pineapple Upside Down Cake is a classic dessert with a buttery, moist cake, signature caramelized pineapple, and cherry-studded topping.

If you are looking for more classic fruit desserts, I think you’ll love my easy peach cobbler, strawberry shortcake, and chocolate-covered strawberries.

Few cakes are as nostalgic and classic as the pineapple upside-down cake. A timeless cake crowned with caramelized topping and pineapple rings studded with bright cherries in the center.

Each delicious bite takes me back to my childhood and watching Mama magically flip the pineapple upside-down cake onto her cake plate without even a smidgen of the cake sticking to the skillet.

There’s really nothing like it.

How to Make the Best Pineapple Upside-Down Cake Recipe

Ingredients

Be sure to see the recipe card below for the full listing of ingredients, instructions, notes, and estimated nutritional information.

For the topping

• Butter – you’ll use melted butter to coat the cake pan or skillet to prevent the cake from sticking and to help create the signature caramelized topping.
• Brown sugar –  the brown sugar melts into the melted butter to form the caramelized topping of the cake.
• Pineapple slices – The most iconic part of the cake that gives it sweetness and its name! I like to place the pineapple rings around the top of the cake, but if you like you can also include slices of the pineapple rings up the sides of the cake pan or skillet to decorate the sides of the cake as well. Be sure to use pineapple slices that are canned in juice and not syrup as the syrup is too sweet. Reserve the canned juices to use in the cake batter.
• Maraschino cherries – bright, red cherries are an iconic part of the cake topping. They are generally pressed into the center of each pineapple ring. If you prefer, you can also include them in other open areas of the cake topping around the pineapple rings.

For the cake

• Flour – this cake uses all-purpose flour. I measure my flour using the spoon and level method to ensure I add the appropriate amount of flour for the cake batter.
• Baking powder – works to help the cake rise as it bakes. You’ll want to be sure to use fresh baking powder to make sure the cake rises appropriately. Read how to test your baking powder for freshness.
• Baking soda – since this cake uses buttermilk, you’ll also want to use a little baking soda in the recipe. If you’d used all baking soda, it would neutralize all of the buttermilk’s acid. By primarily using baking powder with a little baking soda, we preserve the tanginess of the buttermilk in the recipe.
• Kosher salt – a little kosher salt helps to balance and enhance the flavor of the cake.
• sugar
• Buttermilk – I turn to buttermilk for my pineapple upside-down cake. If you don’t have buttermilk, you can easily make your own using my buttermilk substitutes listing.
• Butter – I use melted in the cake batter. It makes the cake moist, tender, and incredibly delicious.
• Pineapple juice – add some of the reserved pineapple juice from the pineapple slices to give the cake a delicious pineapple flavor.
• Eggs – you’ll need large eggs at room temperature.
• Vanilla extract – use a good quality vanilla extract. I love to use my homemade recipe. It enhances the flavor of the cake.
• Pineapple slices – I love to chop and stir any leftover pineapple slices from the can into the cake batter. It gives little bites of pineapple throughout the cake, which is so delicious.

Step-by-Step Instructions

• Prep. Preheat the oven to 350º F.

Make the topping:

Make the topping. Pour 1/4 cup melted butter into the cake pan. Swirl the pan until the bottom and the inside sides of the cake pan are well-coated with the butter to prevent the cake from sticking. Sprinkle the brown sugar evenly over the melted butter. Arrange the pineapple slices on top of the brown sugar. Place the maraschino cherries in the center of each of the pineapple rings. Add more as you prefer.

Make the cake:

Whisk the flour, baking powder, baking soda, salt, and sugar in a large mixing bowl. Set aside.

Whisk together the buttermilk, remaining 1/4 cup of melted butter, pineapple juice, eggs, and vanilla extract in a separate bowl or large measuring cup.

Whisk into the flour mixture until well combined. Stir in the leftover chopped pineapple.

Pour the cake batter over the pineapple and cherry topping. Spread the cake batter in the pan with an offset spatula or the back of a spoon.

Place in the oven and bake for approximately 45 minutes to 1 hour or until a toothpick or skewer inserted in the center comes out clean. You can follow my tips for how to tell when your cake is done.

Remove the cake from the oven and allow to stand for about 5-10 minutes before transferring to a cake stand.

Run a butter knife or offset spatula around the edges of the cake in the cake pan to make sure the cake has released from the pan. Place the cake stand on top of the cake pan and then carefully turn the cake out onto the cake stand.

Storage Tips

To store. While you can store this cake at room temperature for a day or so, I recommend storing the cake covered in the refrigerator for up to 5 days. To serve, allow to reach room temperature before serving. 

To make ahead. Prepare the cake according to the recipe instructions. Cool the cake completely and cover the cake plate. Store in the refrigerator for up to 5 days. 

To freeze. Cool the cake completely and wrap it or individual slices tightly with plastic wrap topped with foil. Store in a freezer-safe container in the freezer for up to 3 months. To serve, allow to thaw overnight in the refrigerator. Then, remove from the refrigerator and allow to reach room temperature before serving.

Frequently Asked Questions

Here’s my Pineapple Upside Down Cake recipe. I think you’ll love it!

Enjoy!
Robyn xo

This cake recipe was originally published 2011. Updated August 2023 with new step-by-step photographs and clearer instructions.