Next-Level 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!

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

• Measuring cups and Spoons
• 9×13-inch (23x33cm) baking pan
• Small saucepan
• Mixing bowls

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.

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:

• Best-Ever Chocolate Cake with Whipped Chocolate Ganache
• Best-Ever Vanilla Cake
• Best-Ever Carrot Cake
• Best-Ever Vanilla Buttercream Frosting

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

Full (and printable) recipe below!

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Gemma's Best-Ever Vanilla Birthday Cake Recipe

Incredibly Moist Coconut Cake Recipe