Name: Pineapple Upside Down Cake
Prep time: 15 min
Cook time: 40 min
Total time: 55 min
Cuisine: American
Ingredients: 1/4 cup butter (melted); 1/2 cup packed light brown sugar; 7–8 canned pineapple rings (drained); 7–8 maraschino cherries (optional); 1 1/2 cups all-purpose flour; 2 teaspoons baking powder; 1/4 teaspoon salt; 1/2 cup butter (softened); 3/4 cup granulated sugar; 2 large eggs; 1 tablespoon pure vanilla extract; 1/2 cup milk (dairy or plant-based)

Sweet, sticky, and stunning to look at, this Pineapple Upside Down Cake is one of those classic desserts I love pulling out when I want something nostalgic but impressive. The caramelized pineapple slices and buttery brown sugar topping create a luscious layer over a soft vanilla cake that’s irresistible from the very first bite.

Why You’ll Love This Recipe

I love how this cake brings a beautiful combination of texture and flavor — rich, golden fruit on top of a soft, fluffy base. It’s simple to make with pantry staples, yet it always feels special. Whether I’m baking for a family gathering, a casual dinner, or just because, this dessert always brings compliments. Plus, the upside-down flip at the end is so satisfying and fun!

Ingredients

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

For the Topping:

1/4 cup butter (melted)

1/2 cup packed light brown sugar

7–8 canned pineapple rings (drained)

7–8 maraschino cherries (optional)

For the Cake:

1 1/2 cups all-purpose flour

2 teaspoons baking powder

1/4 teaspoon salt

1/2 cup butter (softened)

3/4 cup granulated sugar

2 large eggs

1 tablespoon pure vanilla extract

1/2 cup milk (dairy or plant-based)

Directions

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

Then, I pour the melted butter into the bottom of the pan and sprinkle the brown sugar evenly over it.

I arrange the pineapple slices on top, and if I’m using cherries, I place one in the center of each ring.

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

In a large mixing bowl, I cream the softened butter and sugar until light and fluffy.

Next I beat in the eggs one at a time and stir in the vanilla.

I alternately add the flour mixture and milk into the wet ingredients, beginning and ending with the flour. I stir just until combined.

Then I pour the batter evenly over the pineapple layer in the pan.

I bake the cake for 35–40 minutes, until a toothpick inserted into the center comes out clean.

I let the cake cool in the pan for 10 minutes before inverting it onto a serving plate. After it cools completely, it’s ready to slice and serve.

Servings and timing

This recipe makes 8 servings.

Prep Time: 15 minutes

Cooking Time: 40 minutes

Total Time: 55 minutes

Calories per serving: Approximately 280 kcal

Variations

I like playing with this classic recipe by making a few fun changes:

I sometimes use fresh pineapple slices for a slightly tangier flavor.

For a citrus twist, I add a little orange or pineapple juice to the batter.

I’ve also made a rum version by brushing a bit of dark rum over the pineapple layer after baking.

A mini version in muffin tins makes adorable single-serve cakes.

Swapping out the vanilla for coconut extract gives it a more tropical vibe.

Storage/Reheating

Once cooled, I store leftover cake in an airtight container at room temperature for up to 2 days. If I need to keep it longer, I refrigerate it for up to 5 days.

To reheat, I warm individual slices in the microwave for about 15–20 seconds. If I want to refresh the texture, I sometimes warm slices in the oven at 300°F (150°C) for 10 minutes.

Related Recipes:

Oatmeal Pancakes

FAQs

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

I make sure to generously grease the cake pan before adding the butter and sugar. Letting the cake cool for just 10 minutes before inverting also helps it release cleanly.

Can I use fresh pineapple instead of canned?

Yes, I’ve used fresh pineapple slices with great results. I just make sure they’re sliced thinly and evenly for the best texture and look.

What’s the best way to flip the cake?

I place a plate or serving dish over the top of the cake pan, hold them firmly together with oven mitts, and quickly invert it in one motion. Then I lift the pan off slowly.

Can I make this cake ahead of time?

Absolutely. I often bake it a day in advance. Once cooled, I cover it and store it at room temperature. It tastes even better the next day!

Do I have to use cherries?

No, I skip them sometimes when I want a cleaner look. But when I want that classic vintage appearance, I like adding the bright red cherries.

Conclusion

This Pineapple Upside Down Cake has everything I look for in a go-to dessert — it’s easy, beautiful, and incredibly delicious. Whether I’m serving it for guests or just treating myself, I love how every bite brings that perfect mix of caramelized fruit and tender cake. It’s a timeless favorite I keep coming back to.

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