Name: Pineapple Upside Down Cake
Prep time: 15 min
Cook time: 45 min
Total time: 1 h
Cuisine: American
Ingredients: 1/4 cup unsalted butter, melted; 1/2 cup packed brown sugar; 7–8 pineapple rings (canned or fresh); 7–8 fresh pitted cherries; 1 1/2 cups all-purpose flour; 1 cup granulated sugar; 1/2 cup unsalted butter, softened; 2 large eggs; 1/2 cup milk; 1/4 cup pineapple juice (from the can); 1 1/2 teaspoons baking powder; 1 teaspoon vanilla extract; 1/4 teaspoon salt

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I love how this Pineapple Upside Down Cake brings together a moist buttery vanilla cake with a glossy caramelized pineapple topping. The sweet brown sugar melts into the butter and creates a rich glaze that soaks into the fruit as it bakes. When I flip the cake over, I always admire the beautiful pattern of golden pineapple rings and bright cherries on top. It feels nostalgic, comforting, and perfect for gatherings or simple family desserts.

Pineapple Upside Down Cake

Ingredients

(Tip: You'll find the full list of ingredients and measurements in the recipe card below.)

¼ cup unsalted butter, melted

½ cup packed brown sugar

7–8 pineapple rings (canned or fresh)

7–8 fresh pitted cherries

1 ½ cups all-purpose flour

1 cup granulated sugar

½ cup unsalted butter, softened

2 large eggs

½ cup milk

¼ cup pineapple juice (from the can)

1 ½ teaspoons baking powder

1 teaspoon vanilla extract

¼ teaspoon salt

Directions

I start by preheating the oven to 350°F (175°C) and lightly greasing a 9-inch round cake pan.

I pour the melted butter into the bottom of the prepared pan and spread it evenly. Then I sprinkle the brown sugar evenly over the butter to create the caramel base.

I arrange the pineapple rings over the brown sugar layer and place a cherry in the center of each ring, filling any empty spaces with extra cherries. I set the pan aside while I prepare the batter.

In a medium bowl, I whisk together the flour, baking powder, and salt.

In a large mixing bowl, I cream the softened butter and granulated sugar until the mixture becomes light and fluffy. I add the eggs one at a time, beating well after each addition, then mix in the vanilla extract.

I alternate adding the dry ingredients with the milk and pineapple juice, beginning and ending with the dry ingredients. I mix just until combined and make sure not to overmix.

I carefully spread the batter evenly over the pineapple layer in the pan. Then I bake the cake for 40–45 minutes, or until a toothpick inserted into the center comes out clean.

I let the cake cool in the pan for 10–15 minutes. I run a knife around the edges and carefully invert it onto a serving plate. I allow it to cool slightly before slicing and serving.

Servings and timing

Prep Time: 15 minutes

Cooking Time: 45 minutes

Total Time: 1 hour

Servings: 8 servings

Calories: 360 kcal per serving

Variations

I sometimes add a handful of shredded coconut to the batter for a tropical twist. When I want extra texture, I sprinkle chopped pecans or walnuts over the brown sugar layer before arranging the pineapple rings. I also like experimenting with different fruits, such as peach slices or mango, while keeping the same caramel base. For a richer flavor, I occasionally replace a small portion of the milk with sour cream.

Storage/Reheating

I store any leftover cake covered tightly at room temperature for up to 2 days. If I want to keep it longer, I refrigerate it for up to 5 days. Before serving refrigerated slices, I let them come to room temperature or warm them slightly in the microwave for a few seconds to bring back the soft, buttery texture. I make sure to cover it well so the cake does not dry out.

FAQs

How do I prevent the cake from sticking to the pan?

I make sure to grease the pan well and allow the cake to cool for about 10–15 minutes before inverting it. I also run a knife around the edges to loosen it gently.

Can I use fresh pineapple instead of canned?

I can use fresh pineapple, but I make sure to slice it evenly and pat it dry to prevent excess moisture from affecting the caramel layer.

Why should I not overmix the batter?

I avoid overmixing because it can make the cake dense and tough. I mix just until the ingredients are combined to keep the texture light and tender.

Can I make this cake ahead of time?

I often bake it a day in advance. I keep it covered at room temperature or in the refrigerator, then bring it to room temperature before serving.

Can I freeze Pineapple Upside Down Cake?

I can freeze the cake by wrapping it tightly in plastic wrap and foil. I thaw it overnight in the refrigerator and let it come to room temperature before serving.

Conclusion

I find this Pineapple Upside Down Cake to be a timeless dessert that never goes out of style. The caramelized brown sugar topping, juicy pineapple rings, and soft vanilla cake create a perfect balance of flavor and texture. I love serving it slightly warm and watching everyone admire the glossy fruit topping before taking their first bite. It is simple, beautiful, and always satisfying.

📖 Recipe:

Pineapple Upside Down Cake

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Author: Cheryl
Total Time: 1 hour
Yield: 8 servings
Diet: Vegetarian

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Description

A classic Pineapple Upside Down Cake featuring a moist, buttery vanilla cake topped with caramelized brown sugar, golden pineapple rings, and bright cherries. This nostalgic dessert is simple to make, beautifully presented, and perfect for gatherings or family treats.

Instructions

Preheat the oven to 350°F (175°C) and lightly grease a 9-inch round cake pan.
Pour the melted butter into the bottom of the prepared pan and spread evenly. Sprinkle the brown sugar evenly over the butter.
Arrange the pineapple rings over the brown sugar layer and place a cherry in the center of each ring. Fill any empty spaces with extra cherries and set aside.
In a medium bowl, whisk together the flour, baking powder, and salt.
In a large mixing bowl, cream the softened butter and granulated sugar until light and fluffy. Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract.
Alternate adding the dry ingredients with the milk and pineapple juice, beginning and ending with the dry ingredients. Mix just until combined without overmixing.
Spread the batter evenly over the pineapple layer in the pan.
Bake for 40–45 minutes, or until a toothpick inserted into the center comes out clean.
Cool in the pan for 10–15 minutes. Run a knife around the edges and carefully invert onto a serving plate. Cool slightly before slicing and serving.