This pineapple upside down cake is simple and so delicious! With a sweet brown sugar glaze, plenty of fresh pineapple and cherries, and a soft, moist butter cake. So easy and made completely from scratch!

Square Image of a pineapple upside down cake with cherries on a white cake stand.

Pineapple upside down cake is a total classic! It’s been a favorite dessert here in the US for close to a century, and it’s no wonder why.

With a moist, buttery cake on the bottom, a layer of tropical pineapple and bright cherries, and a sweet brown sugar glaze that infuses every bite with its warm flavor, this is a dessert you’ll want to make again and again.

Vertical image with text overlay of a pineapple upside down cake on a white cake stand with a yellow napkin.

Pineapple upside down cake was a favorite for my dad, and I’m so sad he’s not still here to share a slice with me! I’m sure he would have loved this.

I remember making it for him once when he was still alive, but I don’t think I did such a hot job. I think I probably used a box mix, but now I’m older and wiser and I know that it’s not even any harder to bake from scratch.

(In my opinion, it’s a big conspiracy by the box-mix makers, to make us all think that baking from scratch is so much more difficult than it is. Shh!)

This pineapple upside down cake is made from all fresh ingredients, and it’s easy as can be! You’ll only need to dirty one small pot and one mixing bowl. Not bad at all, right?

Vertical overhead image of a pineapple upside down cake with marbelized plates, copper forks, and a yellow napkin.

You can even use fresh pineapple for the topping. It releases lots of sweet and flavorful juice into the cake as it bakes, making it so moist!

If you’re not sure how to maneuver a fresh pineapple, check out this video: How to Cut a Pineapple. Basically, you follow these steps, only instead of quartering it after taking off the skin, just cut it into slices about half an inch thick. I used an apple corer to cut out the core, and a cookie cutter to neaten up the edges.

But if you don’t want to go to the trouble, that’s totally ok too! You can buy pineapple rings in a can and that will work just as well.

Vertical image of a pineapple upside down cake on a stand with a slice cut out and plated.

The cake layer on the bottom is based on my latest and greatest vanilla cupcake recipe. It’s got a soft, delicate texture and a buttery, vanilla-y flavor that I just can’t get enough of. I love this recipe so much!

I hope you’ll give this pineapple upside down cake a try! It’s great at any time of year, but I especially love it during these warmer months!

Horizontal image of a pineapple upside down cake on a white stand with a slice cut out and placed on a plate in the background.

More great cake recipes on my “Cake Recipes” Pinterest board!


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7 reviews

Pineapple Upside Down Cake

This pineapple upside down cake is simple and so delicious! With a sweet brown sugar glaze, plenty of fresh pineapple and cherries, and a soft, moist butter cake. So easy and made completely from scratch!

Prep Time 25 minutes Cook Time 40 minutes Total Time 1 hour 5 minutes
Serves 8     adjust servings

Ingredients

For the topping

  • 1/4 cup (half a stick) unsalted butter
  • 1 cup (loosely packed) light brown sugar
  • 4 pineapple rings
  • 13 Maraschino cherries

For the cake

  • 3/4 cup cake flour*
  • 1/3 cup all-purpose flour
  • 1/2 cup granulated sugar
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon kosher salt
  • 6 tablespoons unsalted butter, softened
  • 1 large egg
  • 1/3 cup Greek yogurt**
  • 1/4 cup milk
  • 1 teaspoon vanilla extract

Instructions

To make the topping:

  1. Place the butter and brown sugar in a small pot and heat over low heat, stirring, until the butter is melted and the mixture is smooth.
  2. Mist a 9-inch diameter cake pan with non-stick spray, and arrange the pineapple slices and Maraschino cherries in a decorative pattern.
  3. Pour the brown sugar mixture over the pineapple and cherries, in an even layer.

To make the cake:

  1. Preheat the oven to 350 degrees F.
  2. Place the cake flour, all-purpose flour, sugar, baking powder, baking soda, and salt in a mixing bowl and whisk to combine.
  3. Add the softened butter, beating on medium speed until the mixture resembles damp sand (about 2 minutes).
  4. Stir in the egg until incorporated.
  5. Scrape the bottom and sides of the bowl with a silicone spatula, then add the Greek yogurt, milk, and vanilla.
  6. Mix the batter on medium speed for a minute to a minute and a half, to aerate the batter and build the cake's structure.
  7. Transfer the batter to the prepared pan, and bake for 36 to 42 minutes, or until a toothpick inserted in the thickest part of the cake comes out clean.
  8. Cool for 20 minutes in the pan, then invert onto a serving plate to cool completely.

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Recipe Notes

*Cake flour is a fine, light flour milled from hard wheat. It produces a lighter, more tender cake than all-purpose flour would alone. You can buy it on your regular grocery store shelf, in the baking aisle. If you can't find cake flour or don't want to use it, you can substitute all-purpose flour.
**Sour cream or buttermilk can be substituted. If you don't have buttermilk, you can make it by combining 1/4 cup of milk with 1 teaspoon of lemon juice or white vinegar. Allow the mixture to stand for 5 minutes, or until thickened and somewhat curdled.

Nutrition Facts
Serving Size
Amount Per Serving As Served
Calories 404kcal Calories from fat 145
% Daily Value
Total Fat 16g 25%
Saturated Fat 10g 50%
Transfat 1g
Cholesterol 64mg 21%
Sodium 149mg 6%
Carbohydrate 63g 21%
Dietary Fiber 1g 4%
Sugars 47g
Protein 4g

Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs:

Calories 2000
Total Fat Less than 65g
Sat Fat Less than 25g
Cholesterol Less than 300mg
Sodium Less than 2,400mg
Total Carbohydrate 300g
Dietary Fiber 25g

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