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

Golden, gooey, and crowned with caramelized pineapple rings and cherries, Pineapple Upside Down Cake is a timeless dessert that turns heads before the first bite is taken. With its buttery vanilla cake base and glistening fruit topping, this retro classic has earned its place as a staple at family gatherings, potlucks, and festive dinners.

What makes this cake especially appealing is the way its fruity topping and moist crumb come together in each forkful. It’s easy to prepare, visually stunning, and boasts a flavor combination that balances bright tropical sweetness with rich, buttery goodness.

Why You’ll Love This Pineapple Upside Down Cake

Whether you grew up with this cake or you’re trying it for the first time, there’s a lot to adore:

Beautiful Presentation: The glossy pineapple and cherry topping naturally creates a show-stopping finish.
Moist and Fluffy Texture: The cake absorbs juices from the fruit and caramel, staying incredibly soft.
Perfect for All Occasions: From holidays to everyday cravings, it’s a crowd-pleaser.
Make-Ahead Friendly: It tastes even better the next day after the flavors have melded.

Preparation Phase & Tools to Use

Getting the tools right can make baking this cake a breeze and ensure it looks as lovely as it tastes.

9-Inch Round Cake Pan: This is essential for achieving the iconic circular shape with uniform fruit layering.
Mixing Bowls (at least two): One for wet ingredients, another for dry — helps in even mixing.
Hand or Stand Mixer: For a light, fluffy batter. While you can mix by hand, a mixer saves time and effort.
Rubber Spatula: Great for folding ingredients and scraping down bowls without overmixing.
Whisk: Ideal for beating eggs and blending dry ingredients together smoothly.
Cooling Rack: Ensures even cooling and prevents the cake from getting soggy after it’s inverted.

Each tool contributes to the cake’s final texture and look, so make sure to prep your kitchen before diving into baking.

Ingredients for the Pineapple Upside Down Cake

Pineapple Rings: The star of the show, adding juicy sweetness and tropical flair.
Maraschino Cherries: Nestled inside each pineapple ring for a pop of color and subtle tartness.
Brown Sugar: Creates the sticky, caramelized topping that defines this cake.
Unsalted Butter: Adds richness and supports the caramel base.
All-Purpose Flour: Forms the structural base of the cake.
Baking Powder: Helps the cake rise to a fluffy, tender crumb.
Salt: Enhances overall flavor and balances the sweetness.
Granulated Sugar: Sweetens the cake batter.
Eggs: Bind the ingredients and add moisture.
Vanilla Extract: Infuses the batter with warm, aromatic flavor.
Whole Milk: Keeps the crumb soft and moist.

How To Make the Pineapple Upside Down Cake

Step 1: Prepare the Pan and Topping

Preheat your oven to 350°F (175°C). Melt the butter and pour it into the bottom of your 9-inch round cake pan. Sprinkle the brown sugar evenly over the melted butter. Arrange pineapple rings on top, and place a cherry in the center of each ring.

Step 2: Mix the Dry Ingredients

In a mixing bowl, whisk together the flour, baking powder, and salt. This ensures your leavening is evenly distributed throughout the batter.

Step 3: Cream the Butter and Sugar

Using a mixer, beat the softened butter and granulated sugar together until pale and fluffy. This step incorporates air, giving the cake its light texture.

Step 4: Add the Eggs and Vanilla

Beat in the eggs one at a time, then add the vanilla extract. Mix until fully combined.

Step 5: Combine Wet and Dry Ingredients

Gradually alternate adding the flour mixture and milk to the batter, beginning and ending with flour. Mix until just combined, avoiding overmixing.

Step 6: Assemble and Bake

Pour the batter gently over the arranged pineapple and cherries. Spread it evenly with a spatula. Bake for 40–45 minutes or until a toothpick inserted in the center comes out clean.

Step 7: Cool and Invert

Let the cake rest for about 10 minutes in the pan. Run a knife around the edges, place a serving plate over the pan, and invert carefully. Let it cool completely before serving.

Serving and Storing Pineapple Upside Down Cake

Serve warm or at room temperature for the most delightful experience. The caramelized topping shines best when slightly warm, making it perfect as a comforting dessert with a scoop of vanilla ice cream or dollop of whipped cream.

To store, keep the cake covered at room temperature for up to 2 days. For longer storage, refrigerate it in an airtight container for up to 5 days. You can reheat individual slices in the microwave for 10–15 seconds to bring back that just-baked warmth.

To freeze, wrap the cake tightly in plastic wrap followed by foil. It can be frozen for up to 2 months. Thaw overnight in the fridge and warm before serving.

Frequently Asked Questions

What kind of pan should I use?

A 9-inch round cake pan is traditional and works perfectly for this recipe. Avoid springform pans, as the caramel can leak out during baking.

Can I use fresh pineapple instead of canned?

Yes! Just be sure to slice it thinly and remove any tough cores. Canned rings are more uniform and quicker to use but fresh adds a lovely natural sweetness.

Why did my cake stick to the pan?

Ensure your pan is well-greased with butter and the topping is fully covering the base before adding the batter. Also, inverting while the cake is still warm (after 10 minutes of resting) helps it release cleanly.

Can I make it ahead of time?

Absolutely. This cake is delicious the next day as the flavors deepen. Just store it covered at room temp or in the fridge depending on how long you plan to keep it.

What can I serve with Pineapple Upside Down Cake?

Try it with whipped cream, vanilla ice cream, or even a light coconut glaze for a tropical touch.

Can I make this gluten-free?

Yes, substitute the all-purpose flour with your favorite 1:1 gluten-free baking mix. Be mindful of changes in texture and check for doneness as baking time may vary slightly.