Moist Pineapple Upside Down Cake
This Pineapple Upside Down Cake is a timeless dessert that’s as beautiful as it is delicious. With caramelized pineapple rings, sweet maraschino cherries, and a soft, buttery cake, every slice is packed with classic flavor. The brown sugar topping creates a rich caramel glaze as the cake bakes, and once flipped, reveals a stunning golden fruit topping that’s perfect for family gatherings, potlucks, holidays, or simply enjoying with a cup of coffee. This easy homemade version delivers all the nostalgic charm of the traditional recipe with a moist, tender crumb that keeps everyone coming back for another slice.
How to Make Pineapple Upside Down Cake
Start by preheating your oven to 350°F (175°C/Gas Mark 4). While the oven is heating, prepare the signature pineapple topping. Pour the melted butter into the bottom of a pie dish, making sure it evenly covers the surface. Sprinkle the brown sugar over the butter and spread it into an even layer. Arrange the pineapple slices neatly across the bottom of the dish, then place the maraschino cherries in the spaces between the pineapple rings. For a beautiful presentation, cut three pineapple slices in half and arrange them around the sides of the pan. Once the topping is assembled, place the dish in the refrigerator while you prepare the cake batter.
In a medium bowl, whisk together the flour, baking powder, baking soda, and salt until well combined. In a separate large mixing bowl, cream the softened butter and granulated sugar together until light and fluffy, scraping down the sides of the bowl as needed. Add the eggs, vanilla extract, and milk, then continue beating for several minutes until smooth and fully incorporated.
Gradually add the dry ingredients to the wet ingredients and mix until a thick batter forms. Pour in the pineapple juice and stir just until combined, being careful not to overmix. Remove the prepared pineapple topping from the refrigerator and gently spread the cake batter over the fruit layer.
Bake for 45–50 minutes, or until a knife inserted into the center comes out clean or with just a few crumbs attached. Allow the cake to cool in the pan for about 20 minutes before carefully inverting it onto a serving plate or cake stand. Don’t worry if some of the caramelized topping drips down the sides—that’s part of its charm. Let the cake cool completely before slicing and serving. Serve with a dollop of whipped cream or creamy vanilla ice cream!
For another comforting homemade dessert, try this classic bread pudding with cinnamon and vanilla.
Storage
Store leftover Pineapple Upside Down Cake covered in the refrigerator for up to 5 days. The fruit topping helps keep the cake moist and flavorful.
Freeze individual slices or the entire cake for up to 3 months. Wrap tightly in plastic wrap followed by aluminum foil or place in an airtight freezer-safe container.
Thaw overnight in the refrigerator if frozen. Enjoy chilled, bring to room temperature, or warm individual slices in the microwave for 15–20 seconds before serving.
Ingredients
Pineapple Topping
Unsalted Butter: forms the base of the caramelized topping. As it melts and combines with the brown sugar, it creates a rich, buttery sauce that coats the pineapple and gives the cake its signature golden finish.
Brown Sugar: adds sweetness and deep caramel flavor to the topping. During baking, it melts into the butter, creating a delicious glaze that soaks into the pineapple and enhances the overall richness of the cake.
Pineapple Slices: are the star of this classic dessert. They become tender and caramelized as the cake bakes, adding a sweet, juicy, tropical flavor to every slice.
Maraschino Cherries: add a pop of color and sweetness to the topping. Their bright red hue creates the traditional pineapple upside down cake appearance and makes the finished cake especially beautiful.
Vanilla Cake
All-Purpose Flour: provides the structure for the cake. It creates a soft yet sturdy crumb that supports the fruit topping while remaining tender and moist.
Baking Powder: helps the cake rise as it bakes, creating a light and fluffy texture.
Baking Soda: works alongside the baking powder to provide additional lift and contribute to the cake’s tender crumb.
Salt: A small amount of salt enhances the sweetness of the cake and balances the flavors throughout the batter.
Unsalted Butter: Butter adds richness, moisture, and flavor to the cake. It also helps create a soft, tender texture when creamed with the sugar.
Granulated Sugar: sweetens the cake and contributes to its light texture. When creamed with butter, it helps incorporate air into the batter for a fluffy result.
Eggs: provide structure, moisture, and richness. They help bind the ingredients together and contribute to the cake’s soft, delicate texture.
Vanilla Extract: adds warm, sweet flavor that complements both the pineapple topping and the buttery cake.
Whole Milk: adds moisture and richness to the batter, helping create a soft and tender crumb.
Pineapple Juice: enhances the tropical flavor of the cake and adds extra moisture. It ties the vanilla cake and pineapple topping together for a perfectly balanced dessert.
Try my other delicious cake recipes!
- Pumpkin Cake with Cream Cheese Icing
- Lemon Loaf Cake
- Carrot Cake with Cream Cheese Frosting
- Strawberry Pound Cake Recipe
- No-Bake Cherry Cheesecake
Pineapple Upside Down Cake Recipe
Ingredients
Topping
- 1/4 c. unsalted butter
- 1/2 c. brown sugar
- 10 pineapple slices
- maraschino cherries
Vanilla Cake
- 1 1/2 c. all-purpose flour
- 1 tsp. baking powder
- 1/2 tsp. baking soda
- 1/2 tsp. salt
- 1/2 c. unsalted butter
- 3/4 c. granulated sugar
- 2 eggs
- 1 tsp. vanilla extract
- 1/4 c. whole milk
- 1/4 c. pineapple juice
Instructions
- Preheat the oven to 350℉/175℃/Gas Mark 4.
Pineapple Topping
- Pour the 1/4 c. unsalted, melted butter into the bottom of the pie dish. Sprinkle the brown sugar over top of the melted butter and evenly spread on the bottom of the dish. Arrange the pineapple slices evenly on the bottom of the dish and place the cherries in between the pineapple slices. Halve 3 pineapple slices and place them around the sides of the pan. Place the pan into the fridge while preparing the cake batter.
Vanilla Cake Batter
- In a medium bowl, whisk the all-purpose flour, baking powder, baking soda, and salt together. Set aside.
- In a large bowl, cream the softened butter with the granulated sugar. Scrape the sides of the bowl as needed. Add the eggs, vanilla extract, and whole milk. Continue to beat on medium speed for another 3-4 minutes.
- Add the dry ingredients to the wet ingredients and continue to beat on medium speed until a thick batter is formed. Add the pineapple juice to the mixture and beat until just incorporated. Do not overmix.
- Remove the prepared topping from the fridge and pour the vanilla cake batter on top of the pineapple topping. Place into the oven and bake for 45-50 minutes or until a knife inserted into the centre of the cake comes out clean or only has a few crumbs on it.
- Remove the cake from the oven and let it cool in the pie dish for 20 minutes. Invert the cake onto a cake stand or serving plate. Some of the topping will run down the sides, which is ok! Let it completely cool before serving and enjoy!
Notes
Author: Sarah Young
Frequently Asked Questions
Can I use canned pineapple for pineapple upside down cake?
Yes! Canned pineapple rings are the traditional choice and work perfectly for this recipe. Be sure to drain them well before using.
Can I use fresh pineapple instead?
Absolutely. Fresh pineapple can be sliced into rings and used in place of canned pineapple, although canned pineapple often provides a more consistent texture and sweetness.
Why is my cake sticking to the pan?
Allow the cake to cool for about 10–15 minutes before inverting. Waiting too long can cause the caramel topping to harden and stick.
Can I make pineapple upside down cake ahead of time?
Yes. This cake can be baked a day in advance and stored covered at room temperature or in the refrigerator until ready to serve.
Do I have to use maraschino cherries?
No. While cherries are traditional, you can leave them out or substitute with pecans, walnuts, or additional pineapple pieces.
Can I use a boxed cake mix?
Yes. A vanilla or yellow cake mix can be used if you’re looking for a quicker version of the recipe.
How do I know when the cake is done baking?
Insert a toothpick into the center of the cake. If it comes out clean or with a few moist crumbs, the cake is ready.
Can I make this cake in a cast iron skillet?
Yes. A cast iron skillet is a classic choice for pineapple upside down cake and helps create a beautifully caramelized topping.
Should pineapple upside down cake be refrigerated?
Because of the fruit topping, refrigeration is recommended if the cake will be stored for more than a day.
Why is my topping runny?
Excess moisture from the pineapple can thin the topping. Be sure to drain canned pineapple thoroughly before arranging it in the pan.
What can I serve with pineapple upside down cake?
This cake is delicious served on its own or topped with whipped cream, vanilla ice cream, or a dollop of freshly whipped cream for an extra-special dessert.