This Old Fashioned Pineapple Upside Down Cake recipe is easy to make and sure to become a family favorite. It’s made with a simple yellow cake base topped with pineapples and maraschino cherries that are all glazed in a delicious butter and brown sugar caramel.
Best Pineapple Upside Down Cake
Some food trends come and go, but an Old Fashioned Pineapple Upside Down Cake is one of those classic desserts that will never go out of style. It gets its name because it’s built upside down, starting with the butter and brown sugar caramel layer, then the pineapple cherry topping and finally the cake batter on top. As it bakes, the caramel seeps throughout the entire thing, creating the most deliciously moist and tender cake.
When it comes out of the oven, let the cake cool for just a few minutes before holding your breath and inverting onto a pretty serving plate for the big reveal. In our opinion, this is the absolute best Pineapple Caramel Upside Down Cake - dense, moist, sweet, stunning and super easy.
If you like this recipe, you may also want to try our Old Fashioned Pineapple Cake made with crushed pineapples in the batter and topped with a thick and creamy caramel.
Upside Down Pineapple Cake Ingredients
- Butter - you can use salted or unsalted butter for the caramel topping, depending on your own preference.
- Brown Sugar - I prefer dark brown sugar because it makes a deeper caramel, but light brown sugar works great too.
- Pineapple Rings - you’ll need one 20-oz can or around 10 sliced rings of fresh pineapple. You can also use pineapple chunks - it all works!
- Maraschino Cherries - I like to slice these in half so that they are about the same width as the pineapples.
Yellow Cake Batter
- Sugar - this cake batter uses regular white granulated sugar.
- Butter - your butter needs to be room temperature so that it will cream properly with the sugar.
- Eggs - it’s best if your eggs are room temperature when you add them to the batter so that they don’t cause the butter to seize up. You can run them under warm water for a minute, or leave them out for about 30 minutes before mixing.
- Milk - whole milk is best.
- Pineapple Juice - you can use the juice reserved from your can of pineapples. If you used fresh, just purchase a small can of pineapple juice.
- Vanilla Extract - pure vanilla extract tastes best.
- Flour - this recipe calls for all-purpose flour, although cake flour works great too.
- Baking Powder - this helps the cake rise a bit and keeps it soft.
- Salt - sea salt works great.
How to Make Pineapple Upside Down Cake With Yellow Cake Mix
- Make the caramel layer. In a medium saucepan, melt the butter, and add the brown sugar. Whisk together, then bring to a boil. Boil for about 30 seconds, whisking constantly, then pour into the bottom of a greased 12-14” round cake pan.
- Arrange pineapple and maraschino cherries. Arrange the pineapple slices in the bottom of the cake pan and add a cherry into the center of each pineapple, or as desired.
- Make the yellow cake batter. In the bowl of a stand mixer, cream together the butter and sugar until fluffy using the paddle attachment. Add the eggs one at a time, scraping down the bowl as needed. Add the milk, pineapple juice, and vanilla extract and mix until combined. In a large bowl, whisk together the flour, baking powder, and salt then add the flour mixture to the wet ingredients. Mix just until all ingredients are combined.
- Bake. Pour the cake batter into the prepared baking dish over the caramel and pineapples and bake for 35-40 minutes, or until the top is golden and a toothpick inserted into the center comes out clean.
- Cool then invert. Remove from the oven, let cool for about 10 minutes, then place a cake stand or serving tray over the cake. Carefully run a sharp knife around the edge of the cake pan, then using hot pads, turn the cake upside down and remove the pan.
- Serve. Let the cake cool for another 10 minutes before slicing. Serve warm or cool with whipped topping. Enjoy!
Frequently Asked Questions
Sure! If you choose to use fresh pineapples, you’ll want to cut them into approximately ½” rings. A 20-oz can has about 10 rings, so you can use that for an estimate of how much you will need.
This is a common problem since there is so much liquid inside of pineapples. The best way to avoid this is to blot the pineapples with paper towels just before adding in the cake batter. You’ll also want to make sure that the cake is fully cooked in the middle, which you can do by inserting a toothpick into the center to see if it comes out clean.
This is a terrible feeling - you spend all of this time baking a cake and then it sticks! The best ways to avoid this are to grease your pan before adding anything into it, and making sure that your cake is still quite how when you flip it over. If you let it cool too long, the caramel on top will begin to set up and stick to the pan.
If you don't have a large round cake pan, you could also bake this in a 9"x13" baking dish. The cake will be a bit thinner, so the baking time will be slightly less. Just keep an eye on it and test by sticking a toothpick into the center to check if it comes out clean.
Upside Down Pineapple Cake Tips
- You can skip making homemade yellow cake mix and use a box of cake mix. If so, use the pineapple juice to substitute for the water when making the yellow cake mix.
- Let the cake cool for a couple of minutes after baking before turning it.
- If a small part of your cake sticks to the bottom of the pan when turning, just scrape it off as best you can and add it back to the cake.
- Serve warm with whipped topping or vanilla ice cream.
Storing and Freezing
- Refrigerator: store leftover slices of cake covered or in an airtight container for up to 3 days in the refrigerator. Before eating, we recommend letting it come to room temperature for at least 30 minutes.
- Freezer: you can freeze slices, too, for up to 2 months. To thaw, pull them out to room temperature for about 1 hour.
Pineapple Upside Down Cake Recipe
- ¼ cup Butter
- ⅔ cup Dark Brown Sugar
- 1 20-ounce can Pineapple Rings reserve ½ cup juice
- 8-10 Maraschino cherries whole or sliced in half
Yellow Cake Batter
- 1 ½ cups Sugar
- ½ cup Butter room temperature
- 3 large Eggs
- ½ cup Milk
- ½ cup Pineapple Juice reserved from canned pineapple
- 1 teaspoon Vanilla Extract
- 2 cups All-Purpose Flour
- 3 ½ teaspoons Baking Powder
- 1 teaspoon Salt
- Preheat oven to 350 degrees.
- Grease a 12-14" round baking pan and set aside.
- In a medium saucepan, melt the butter, and add the brown sugar. Whisk together, then bring to a boil. Boil for about 30 seconds, whisking constantly, then pour into the bottom of your greased cake pan.
- Arrange the pineapple slices and cherries in the bottom of the cake pan as desired.
Yellow Cake Batter
- In the bowl of a stand mixer, cream together the butter and sugar until fluffy using the paddle attachment. Add the eggs one at a time, scraping down the bowl as needed. Add the milk, pineapple juice, and vanilla extract and mix until combined.
- In a large mixing bowl, whisk together the flour, baking powder, and salt then add to the wet ingredients. Mix just until all ingredients are combined.
- Pour the cake batter into the prepared baking dish with the caramel and pineapples and bake for 35-40 minutes, or until the top is golden and a toothpick inserted into the center comes out clean.
- Remove from the oven, let cool for about 10 minutes, then place a cake stand or serving tray over the cake. Carefully run a sharp knife around the edge of the cake pan, then using hot pads, turn the cake upside down and remove the pan.
- Let the cake cool for another 10 minutes before slicing. Serve warm or cool with whipped topping. Enjoy!
More Of the Best Classic Cake Recipes to Try
- Carrot Cake
- Funfetti Bundt Cake
- Lemon Blueberry Buttermilk Cake
- Coconut Zucchini Cake with Caramel Glaze
- Gingerbread Cake
- Lemon Poppy Seed Bundt Cake
- Pumpkin Cake with Cream Cheese Frosting
- Banana Cake
- More Easy Cake Recipes
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This Pineapple Upside Down Cake is a classic dessert that will never go out of style. It's got a simple yellow cake base topped with pineapples and cherries that are all glazed in a delicious butter and brown butter caramel.