Cakes

Next-Level Pineapple Upside-Down Cake

4.5 from 6 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.

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 large bowl, cream together the butter, dark brown sugar, and granulated sugar until light and fluffy.
  6. Whisk in the eggs, milk, reserved pineapple juice, and vanilla extract.
  7. In a medium bowl, combine the flour, baking powder, and salt. Then, fold the dry ingredients into the wet ingredients until just combined.
  8. Carefully spread the batter over the pineapples and bake for about 35-40 minutes, or until a wooden skewer inserted into the center comes out clean.
  9. Allow the cake to cool for 10 minutes in the pan before inverting it 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

4.5 from 6 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 vthe 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 large bowl cream together the butter, dark brown sugar and granulated sugar until light and fluffy.
  • Whisk in the eggs, milk, reserved pineapple and vanilla extract and stir to combine.
  • In a medium mixing bowl, combine the flour, baking powder and salt, and then fold this into the wet ingredients until just combined.
  • 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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lucylixiang

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Linda K

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Carly Baughman
Carly Baughman
5 days ago

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

Liz
Liz
27 days 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.

Fairy
Fairy
1 month ago

Hi there Gemma, can I use this recipe to make the cake in a 8 inch round pan?

Linda K
1 month 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 K
1 month ago

Hi, why is the brown sugar and butter divided ? Is it meant to be 1/2c in each stage as it’s written?

lucylixiang
1 month ago

So happy with how this turned out! So moist and flavourful. Will 100% be making again. Thanks again Gemma, your recipes are fantastic 🙂

Amy
Amy
1 month ago

Hi Gemma. What do you mean when you say divided in the ingredients?

Ramya
1 month ago

Will be making this soon will try with vegan butter for the caramel and cake as am dairy free perffevy for my birthday on 19 September and after office snacks will dm you if i make this and let you know how it goes Thanks Ramya

Karren
Karren
1 month ago

Hi Gemma
This is an iconic cake for me !!!
My Mom used to make it frequently. Such a showy display for such ease of preparation. In the video you mention almond extract but it is not in written in your recipe. Could you ket us know the amount?

Geraldine Healy
Geraldine Healy
1 month ago

Sounds Devine, I’m sitting at my desk in work, dreaming about making this at the weekend.

About Us

Meet Gemma

About Us

Meet Gemma

Hi Bold Bakers! I’m Gemma Stafford, a professional chef originally from Ireland, and I want to help you bake with confidence anytime, anywhere! No matter your skills, I have you covered. Sign up for my FREE weekly emails and join millions of other Bold Bakers in the community for new recipes, baking techniques, and more every week!