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Hi Bold Bakers!
WHY YOU’LL LOVE THIS RECIPE: This best pineapple upside-down cake is a perfect mix of classic and next-level deliciousness.
- Quick Prep: Ready in under an hour, with just 20 minutes of prep time.
- Rich Flavor: Caramelized pineapple and cherries on top of a soft, buttery cake.
- Minimal Cleanup: Requires only a few pans and bowls—perfect for easy baking.
- Versatility: Enjoy it year-round for any occasion, from casual gatherings to special celebrations.
I think I grew up at the perfect time when pineapple upside-down cakes were at their peak. The cake base is a simple Madeira mix, a staple in Irish baking. As kids, we made this cake often in our house, and it’s a great recipe to make with children. Plus, you can easily mix it up using an electric hand mixer in no time. A little baker’s tip: you can prepare and assemble the cake up to a day in advance and keep it in the fridge before baking—making it a perfect choice for easy entertaining!
Bold Bakers Loved This!
“I made this leaving out the almond extract because of nut allergies. I also used deep muffin containers instead so that they came out as individual servings. It worked out very well with a pineapple ring & cherry topping each one.” — Liz
“THIS LEVEL UP PINEAPPLE UPSIDE DOWN CAKE IS AMAZING! I MADE IT LAST WEEK AND MY FAMILY FELL IN LOVE! THANK YOU.” — Lin
“I made this cake and it was delicious! I did cut down on the amount of sugar though. I have another one in the oven now as I’m making it for my brother in law’s birthday. I have doubled up the ingredients to make it extra large.” — Joelle
IMPORTANT NOTE: This recipe was improved and updated on 3/25/2025, to include NEW step-by-step photography, explanations and substitutes of key ingredients, make-ahead and storage instructions, answers to the most frequently asked questions, and Pro Chef Tips.
Table of Contents
- What is a Pineapple Upside-Down Cake?
- Tools You Need
- Key Ingredients and Substitutes
- How to Make a Pineapple Upside-Down Cake
- Gemma’s Pro Chef Tips
- Make-Ahead and Storage Instructions
- FAQs
- More Best Cake Recipes
What is a Pineapple Upside-Down Cake?
A pineapple upside-down cake is a classic dessert that bakes with its topping on the bottom, creating a beautiful, caramelized fruit layer once flipped.
- Caramelized Topping: Brown sugar and butter are melted together, then pineapple rings and maraschino cherries are layered on top.
- Baking Magic: As the cake bakes, the pineapple caramelizes and soaks into the soft, yellow cake below.
- Irresistible Texture: Once flipped, the pineapple and cherries stay on top, giving the cake a moist and flavorful finish.
- Perfect for Sharing: Ideal for a small crowd, it pairs beautifully with tea or coffee.
Tools You Need
- Mixing bowls
- Measuring spoons
- Measuring cups
- Glass measuring jug
- Mixing bowls
- 9×13-inch (23×33 cm) cake pan
- Parchment paper
- Whisk
Key Ingredients and Substitutes
Butter
- Adds moisture, richness, and flavor to both the topping and the cake batter. Either salted butter or unsalted butter will work.
- Substitute: Margarine for a dairy-free version.
Brown Sugar
- Provides sweetness and creates a caramelized topping that adds flavor and moisture to the cake.
- Substitute: White sugar mixed with a small amount of molasses.
Pineapple Rings
- Pineapple is high in vitamin C and a good source of fiber. It offers a mix of simple and complex carbohydrates, making it a satisfying snack in moderation.
- Canned pineapple rings provide the signature topping and taste of the cake.
- Substitute: Other fruits like peaches, pears, or apricots, though pineapple gives the most classic result.
Maraschino Cherries
- Adds a sweet and tart burst of flavor and a vibrant pop of color to the cake.
- Substitute: Fresh cherries, glacé cherries, or even a berry-like raspberry for a twist.
All-Purpose Flour
- Provides structure to the cake.
- Substitute: Cake flour (for a lighter texture), gluten-free all-purpose flour (for a gluten-free version), or almond baking mix.
Baking Powder
- Acts as a leavening agent to help the cake rise and become light and fluffy.
Granulated Sugar
- Sweetens the cake and helps with browning.
- Substitute: Coconut sugar, maple syrup (use less liquid in the batter), or honey.
Eggs
- Binds the ingredients together, adds moisture, and helps with leavening.
- Substitute: Flax eggs (1 tablespoon ground flaxseed mixed with 3 tbsp water for each egg) or applesauce (¼ cup/2floz/60ml for each egg).
Whole Milk
- Adds moisture and richness to the batter.
- Substitute: Buttermilk (for a tangy flavor), coconut milk, or any plant-based milk (almond, oat, soy).
Almond Extract
- Adds a nutty, aromatic flavor to the cake.
How to Make a Pineapple Upside Down Cake
To Make The Caramel
- Prep: Preheat the oven to 350°F (180°C) and generously butter a 9 x 13-inch (23 x 33 cm) baking pan. Set aside.
- In a small saucepan over medium-low heat, combine butter and brown sugar and simmer until the sugar is dissolved in about 2-3 minutes. Pour into the prepared baking pan.
- Drain the pineapple rings and reserve ½ cup (4floz/120ml) of juice. Arrange as many rings 4 x 3 or as you can fit in a single layer in the pan on top of the butter and brown sugar mixture.
- Place a maraschino cherry in the center of each pineapple ring.
To Make The Cake
- Mix dry ingredients: In a medium mixing bowl, combine the flour, baking powder and salt, mix well and set aside.
- Cream butter and sugar: Using a stand electric mixer (or electric hand mixer) cream together the butter with both sugars on high speed until light and fluffy, around 3 minutes.
- Add eggs: Whisk in one egg at a time until fully incorporated.
- Then mix in the flour mixture until it comes together and resembles bread crumbs.
- Add wet ingredients: Slowly stream in milk, reserved pineapple juice and almond extract. Mix until just combined and the batter is light and fluffy.
- Carefully spread the batter over the pineapple slices and then bake for 35-40 minutes, until a toothpick inserted into the center comes out clean.
- Let the cake cool for 10 minutes in the pan before inverting onto a serving platter.
Full RECIPE (PRINTABLE) BELOW!
Gemma’s Pro Chef Tips for The Best Pineapple Upside Down Cake Recipe
- Use Fresh Pineapple: Elevate with fresh fruit: You can use fresh pineapple for this recipe. Peel, core, and slice it to 1/2 inch thick. If you do this, replace the reserved can juice with ½ cup (4floz/120ml) of pineapple or orange juice in the cake batter.
- Fresh Cherries: Upgrade with homemade glacé cherries: If you have fresh cherries, make homemade glacé cherries instead of using store-bought maraschino cherries for a more authentic flavor.
- Perfect Inversion: Let it rest for easy flipping. Be sure to invert the cake while it is still warm, but not hot out of the oven. Let it rest for 10 minutes before flipping to prevent it from sticking or breaking.
- Coconut Whipped Cream: Add a creamy, dairy-free topping. This cake is delicious served with coconut whipped cream. Refrigerate a can of full-fat coconut milk, scoop out the solids, discard the liquid, and whip until soft peaks form.
- Pineapple Rum Twist: Infuse with tropical flavor. Make a pineapple rum upside-down cake by stirring 2 tablespoons of rum into the butter and brown sugar mixture before pouring it into the pan.
Make Ahead and Storage Instructions
Make-Ahead:
- You can assemble the pineapple upside-down cake up to 1 day before baking. Simply prepare the topping, layer the pineapples and cherries, and spread the batter over them. Cover the pan tightly with plastic wrap and refrigerate.
- When ready to bake, remove from the refrigerator and bake as directed. This is perfect for easy entertaining!
Storage:
- The cake is best enjoyed the day it’s made for optimal flavor and moisture. However, if you have leftovers:
- Store in an airtight container at room temperature for up to 2 days.
- For longer storage, refrigerate the cake for up to 4 days. Before serving, you can reheat slices in the microwave for a few seconds to refresh the cake.
FAQ
Yes, you can use fresh pineapple! Just peel, core, and slice it into 1/2-inch thick rings. Substitute 1/2 cup (4floz/120ml) of pineapple or orange juice in the batter instead of the reserved canned juice.
To prevent sticking, make sure to generously butter your pan and let the cake rest for 10 minutes after baking before inverting. This helps the cake release without breaking.
Yes! You can prepare the cake the day before. Assemble it and store it in the fridge, then bake it when ready to serve. This is great for easy entertaining!
Absolutely! While pineapple and cherries are classic, you can experiment with other fruits like peaches or even berries for a twist. Just make sure they’re cut into similar sizes for even baking.
Coconut whipped cream, vanilla ice cream, or even a dollop of whipped cream make excellent accompaniments. You can also drizzle it with a little caramel sauce for extra sweetness.
Get more of my Best Cake Recipes:
- Best-Ever Chocolate Cake with Whipped Chocolate Ganache
- Best-Ever Vanilla Cake
- Best-Ever Carrot Cake
- Best-Ever Vanilla Buttercream Frosting
IMPORTANT NOTE: This recipe was improved and updated on 3/25/2025, to include NEW step-by-step photography, explanations and substitutes of key ingredients, make-ahead and storage instructions, answers to the most frequently asked questions, and Pro Chef Tips.
Try These Recipes!
Watch The Recipe Video!
Best Pineapple Upside Down Cake
Ingredients
For the Caramel
- ½ cup (4 oz/115 g) butter
- 1 ¼ cups (7½ oz/213 g) dark brown sugar
- 2 cans (20 oz/567 g) sliced pineapple in juice (12 slices)
- 10-13 maraschino cherries (stems removed)
For the Cake
- 2 cups (10 oz/284 g) all-purpose flour
- 2 teaspoons baking powder
- ½ teaspoon salt
- ½ cup (4 oz/115 g) butter, softened
- ½ cup (4 oz/115 g) granulated sugar
- ⅓ cup (2 oz/57 g) dark brown sugar
- 2 large eggs, at room temperature
- ½ cup (4 fl oz/120 ml) whole milk
- ½ cup (4 fl oz/120 ml) juice from the tinned pineapple
- 1 teaspoon almond extract
Instructions
To Make The Caramel
- Preheat the oven to 350°F (180°C) and generously butter a 9×13-inch (23x33cm) baking pan. Set aside.
- In a small saucepan over medium-low heat, combine butter and brown sugar and simmer until the sugar is dissolved in about 2-3 minutes. Pour into the prepared baking pan.
- Drain the pineapple rings and reserve ½ cup (4floz/120ml) of juice. Arrange as many rings 4 x 3 or as you can fit in a single layer in the pan on top of the butter and brown sugar mixture.
- Place a maraschino cherry in the center of each pineapple ring.
To Make The Cake
- In a medium mixing bowl, combine the flour, baking powder and salt, mix well and set aside.
- Using a stand mixer (or electric hand mixer) cream together the butter with both sugars on high speed until light and fluffy, around 3 minutes.
- Whisk in one egg at a time until fully incorporated.
- Then mix in the dry ingredients until it comes together and resembles bread crumbs.
- Slowly stream in milk, reserved pineapple juice and almond extract. Mix until just combined and the batter is light and fluffy.
- Carefully spread the batter over the pineapples and then bake for 35-40 minutes, until a wooden skewer inserted into the center comes out clean.
- Let the cake cool for 10 minutes in the pan before inverting onto a serving tray.
- This cake is best the day it is made, but you can store leftovers covered at room temperature for up to 2 days.
Recipe Notes
- Use Fresh Pineapple: Elevate with fresh fruit: You can use fresh pineapple for this recipe. Peel, core, and slice it to 1/2 inch thick. If you do this, replace the reserved can juice with ½ cup (4floz/120ml) of pineapple or orange juice in the cake batter.
- Fresh Cherries: Upgrade with homemade glacé cherries: If you have fresh cherries, make homemade glacé cherries instead of using store-bought maraschino cherries for a more authentic flavor.
- Perfect Inversion: Let it rest for easy flipping. Be sure to invert the cake while it is still warm, but not hot out of the oven. Let it rest for 10 minutes before flipping to prevent it from sticking or breaking.
- Coconut Whipped Cream: Add a creamy, dairy-free topping. This cake is delicious served with coconut whipped cream. Refrigerate a can of full-fat coconut milk, scoop out the solids, discard the liquid, and whip until soft peaks form.
- Pineapple Rum Twist: Infuse with tropical flavor. Make a pineapple rum upside-down cake by stirring 2 tablespoons of rum into the butter and brown sugar mixture before pouring it into the pan.
I made this leaving out the almond extract because of nut allergies. I also used deep muffin containers instead so that they came out as individual servings (preferred during these COVID-19 times). It worked out very well with a pineapple ring & cherry topping each one.
I do pretty much the same thing , except I melt the brown sugar, step one of the carmel, directly in the oven in the 9×13. So I don’t need an extra pan
This was a 4 out of 5 for me . It is my all time fav cake so I’m a little snobbish about it LoL . I prefer a higher , fluffier cake. This one reminded me of the Salted Caramel Apple cake that I made before , a little more dense than I like in a PUDC . I also didn’t like how the caramel hardened even before I could throw the pineapple on top of it too. Please Gemma, you don’t have to post this. It’s just my opinion and it is a delicious cake aside from everything… Read more »
Made it today and it was delish! Is a keeper !
In the ingredients it says almond extract but in the instructions it says vanilla?
GEMMA THIS LEVEL UP PINEAPPLE UPSIDE DOWN CAKE IS AMAZING! I MADE IT LAST WEEK AND MY FAMILY FELL IN LOVE! THANK YOU
Hi Gemma, I tried you pineapple cake recipe, the results were not the best. I’ve been baking for 40 years. If I use it again I will tweak it a lot.
Sorry but I followed the recipe exact and this cake had a lot of runny caramel that bubbled over the cake tin in my oven and caused a huge mess ! It also spilt all over my kitchen counters when I tipped the cake over. The cake itself is nice, it was just the massive amount of sugary caramel that spoiled it for me. Not a fan of runny toppings.
Today I made this cake, as per a special request by my best friend for her birthday. Seems the last 4 birthdays she’s had, the pineapple cakes weren’t really what she remembered her mom making for as a child.w We are southern folks so, we’re used to having it a certain way. Seems everyone is like this to some degree and folks familiar with whatever region you may be from and how you were taught. Anyhow.. I’m not really a boxed food kinda maker and after looking through 5 recipes and 6 different videos, I chose this one. Only change… Read more »
I made it and the caramel is too sweet and the almond extract is too strong for the amount the recipe asks (1 tsp). Cut down to half the sugar and almond extract the recipe asks for if you don’t have a sweet tooth.