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Next-Level Pineapple Upside-Down Cake

4.50 from 16 votes
My version of this iconic pineapple-upside down cake recipe is next-level — but keeps the classic pineapple ring and cherry look you know and love.
Top-down view of my pineapple upside down cake.

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Hi Bold Bakers!

I love the way pineapple upside-down cake looks. It reminds me of old cookbooks from the 50s or 60s—but pineapple upside-down cake never goes out of style, especially if you love sweets! 

This cake is perfect for a small crowd, with a pot of warm tea or coffee. It all starts with brown sugar that gets melted in butter and poured into your baking dish. Then you layer in your pineapples and pop a maraschino cheery in the center of each ring. As the cake bakes, the pineapple flavor intensifies and caramelizes. 

Then, you flip the cake out of your pan. Like MAGIC, your pineapple and cherries stay on top of the cake, and all those delicious fruit and caramel juices soak the cake underneath, guaranteeing a beautiful, moist, soft yellow cake!

An entire pineapple upside down cake, with whole pineapple rings and cherries.

What Is Pineapple Upside-Down Cake?

Pineapple upside-down cake is a classic dessert recipe in which you bake it, well, upside-down! When you flip your cake out of your baking dish, then it’s right-side up. Or is it then upside-down? Better not overthink this; it may be a “which came first, the chicken or the egg” situation, and honestly, I rather just think about that soft yellow cake topped with caramelized pineapple. 

What You Need To Make Pineapple Upside-Down Cake

A pineapple cake with a slice removed.

How To Make Pineapple Upside-Down Cake

This cake is so incredibly soft and flavorful, plus you can’t beat that cheerful coloring of pineapple and cherries! Here is how you make pineapple upside-down cake (get the full recipe down below):

  1. Preheat your oven to 350°F (180°C) and generously butter a 9×13-inch (23x33cm) baking pan. Set the pan aside.
  2. Combine the butter and brown sugar in a small saucepan over medium-low heat and let it come to a simmer until the sugar dissolves. This will take 2-3 minutes. Pour this mixture into your prepared baking pan.
  3. Drain the pineapple rings, but save ½ cup (4floz/120ml) of juice. Arrange your rings 4 by 3, or as many as you can fit in a single layer, in the pan on top of the butter and brown sugar mixture.
  4. Place a maraschino cherry in the center of each pineapple ring.
  5. Now, make the cake batter. In a medium mixing bowl, combine the flour, baking powder and salt, mix well and set aside.
  6. In a large bowl cream together room temperature butter, dark brown sugar and granulated sugar until light and fluffy.
  7. To the butter-sugar mixture, whisk in the first egg and cream it until fully incorporated. Add in the second egg and cream it until fully incorporated, too.
  8. Then mix in the dry ingredients until it comes together and resembles bread crumbs.
  9. Slowly stream in milk followed by the reserved pineapple juice.
  10. At last, measure and pour in almond extract. Mix all until just combined and the batter is light and fluffy.
  11. 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.
  12. Let the cake cool for 10 minutes in the pan before inverting onto a serving tray.

Gemma’s Pro Chef Tips For Making Pineapple Upside-Down Cake

  • You can use fresh pineapple for this recipe. Peel, core, and slice it to 1/2 inch thick. If you do this, use ½ cup pineapple or orange juice in the cake batter instead of the reserved can juice.
  • If you have fresh cherries on hand, you can make homemade glacé cherries instead of store-bought maraschino cherries.
  • Be sure to invert the cake while it is still warm but not hot out of the oven. 10 minutes of resting is best. This way, it won’t stick to the pan or break while inverting.
  • This cake is delicious served with coconut whipped cream: place a can of full-fat coconut milk in the refrigerator until cold. Open the can, scoop out the solids (discard the liquid) and whip until soft peaks form.
  • Make this a pineapple rum upside-down cake: stir 2 tablespoons of rum into the butter and brown sugar sauce before pouring it into the pan.

My pineapple cake after baking.

How Do I Store Pineapple Upside-Down Cake?

Because there is so much fruit juice and caramelly goodness, this is a cake that is best enjoyed the day it is made. However, you can store any leftovers in an airtight container at room temperature for up to 2 days.

Get more of my Best Cake Recipes:

And don’t forget to buy my Bigger Bolder Baking Cookbook!

Full (and printable) recipe below!

 

Watch The Recipe Video!

Next-Level Pineapple Upside Down Cake

4.50 from 16 votes
My version of this iconic pineapple-upside down cake recipe is next-level — but keeps the classic pineapple ring and cherry look you know and love.
Author: Gemma Stafford
Servings: 12 people
Prep Time 20 mins
Cook Time 35 mins
My version of this iconic pineapple-upside down cake recipe is next-level — but keeps the classic pineapple ring and cherry look you know and love.
Author: Gemma Stafford
Servings: 12 people

Ingredients

For the Caramel:

  • ½ cup (4oz/115g) butter
  • 1 ¼ cups (7½oz/213g) dark brown sugar
  • 1 large can (20oz/567g) sliced pineapple in juice
  • 10-13 maraschino cherries (stems removed)

For the Cake:

  • ½ cup (4oz/115g) butter, softened
  • ½ cup (4oz/115g) granulated sugar
  • cup (2oz/57g) dark brown sugar
  • 2 large eggs
  • ½ cup (4floz/120ml) whole milk
  • ½ cup (4floz/120ml) juice from the tinned pineapple
  • 1 teaspoon almond extract
  • 2 cups (10oz/284g) all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt

Instructions

To Make The Caramel:

  • Preheat the oven to 350°F (180°C) and generously butter a 9x13-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.
  • In a large bowl cream together room temperature butter, dark brown sugar and granulated sugar until light and fluffy.
  • To the butter-sugar mixture, whisk in the first egg and cream it until fully incorporated. Add in the second egg and cream it until fully incorporated, too.
  • Then mix in the dry ingredients until it comes together and resembles bread crumbs.
  • Slowly stream in milk followed by the reserved pineapple juice.
  • At last, measure and pour in almond extract. Mix all 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 in an airtight container at room temperature for up to 2 days.

 

 

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Liz
Liz
1 year ago

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.

Carly Baughman
Carly Baughman
1 year ago

In the ingredients it says almond extract but in the instructions it says vanilla?

Lin
Lin
4 months ago

Made it today and it was delish! Is a keeper !

Cecilia Clifford
Cecilia Clifford
5 months ago

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

Last edited 5 months ago by Cecilia Clifford
Jon
Jon
8 months ago

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.

Linda K
Linda K
1 year ago

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 »

Linda
Linda
1 month ago

Hi Gemma! Love your recipes! I need to thank you for turning me on to Irish butter a few years ago. I use Kerry Gold. I was amazed at how much more flavorful it is and such a beautiful color! I’m hoping you can suggest good maraschino cherries for baking. I haven’t found good ones like they used to make that are worthy of using in my cherry cake!

Shirley
Shirley
2 months ago

Can I halve the recipe to make in an 8 or 9 inch square pan?

Ellen
Ellen
2 months ago

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.

Ketki
Ketki
3 months ago

Hi Gemma,
I am planning to make this recipe without eggs. I will be using yogurt as egg replacement. Do I need to add baking soda along with baking powder because of the yogurt?

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About Us

Meet Gemma

About Us

Meet Gemma

Hi Bold Bakers! I’m Gemma Stafford, a professional chef originally from Ireland, a cookbook author, and the creator of Bigger Bolder Baking. I want to help you bake with confidence anytime, anywhere with my trusted and tested recipes and baking tips. You may have seen one of my 500+ videos on YouTube & TikTok or as a guest judge on Nailed It! on Netflix or the Best Baker in America on Food Network. No matter your skills, my Bold Baking Team & I want to be your #1 go-to baking authority.

 

Weeknight Family Favorites Chapter from the Bigger Bolder Baking Every Day Cookbook