Name: Classic Pineapple Upside Down Cake
Prep time: 15 min
Cook time: 45 min
Total time: 1 h
Cuisine: American
Ingredients: 7 pineapple rings (canned or fresh); 7 maraschino cherries; 1/2 cup brown sugar; 1/4 cup unsalted butter (for the topping); 1 1/2 cups all-purpose flour; 2 teaspoons baking powder; 1/4 teaspoon salt; 1/2 cup unsalted butter (softened); 3/4 cup granulated sugar; 2 large eggs; 1/2 cup milk; 1 teaspoon vanilla extract

Do you crave a dessert that delivers both nostalgia and elegance with every slice? The Classic Pineapple Upside Down Cake is exactly that—a sweet, golden sponge with caramelized pineapple rings and bright maraschino cherries, flipped to reveal its sunny top only after baking. It’s a retro favorite that never goes out of style, blending tropical tang with buttery richness.

Whether you’re entertaining guests or indulging in a midweek treat, this cake is surprisingly easy to make and visually stunning. The glossy fruit topping, baked right into the base, gives it a built-in decoration that requires no extra fuss. Plus, the flavors only deepen as it sits, making it perfect to prepare ahead of time.

Preparation Phase & Tools to Use

Before diving into the delicious layering of pineapple and batter, it helps to have the right tools at the ready. A 9-inch round cake pan is essential for achieving the traditional shape and even bake. Make sure it’s not non-stick if you want that perfectly caramelized flip.

You’ll also need a mixing bowl and hand mixer or stand mixer to whip up a fluffy batter, ensuring the crumb is light and airy. A rubber spatula will help you fold ingredients smoothly and scrape the bowl clean, leaving no waste behind.

And don’t forget a cooling rack. Allowing the cake to rest before the dramatic upside-down moment keeps the topping intact and avoids a soggy bottom.

Ingredients for the Classic Pineapple Upside Down Cake

Each ingredient plays a key role in the final result of this nostalgic dessert.

Pineapple Rings: The visual star and flavor driver—they caramelize beautifully and provide sweet-tart bursts in every bite.
Maraschino Cherries: Nestled in the center of each pineapple ring, they add color contrast and a pop of sweetness.
Brown Sugar: Essential for that rich, molasses-y caramel layer that forms the sticky top of the cake.
Unsalted Butter: Used in both the topping and batter, it ensures a tender crumb and luxurious flavor.
All-Purpose Flour: Provides the structure needed for the cake to hold its shape after flipping.
Granulated Sugar: Sweetens the batter and balances the tang of the fruit.
Baking Powder: Gives the cake lift and helps it bake up soft and fluffy.
Salt: Enhances the overall flavor and balances the sweetness.
Eggs: Bind the batter together while adding moisture and richness.
Milk: Loosens the batter and creates a tender, moist texture.
Vanilla Extract: Brings warmth and depth to the cake’s flavor.

How To Make the Classic Pineapple Upside Down Cake

Step 1: Prepare the Caramel Base

Melt butter directly in the cake pan and sprinkle brown sugar evenly over it. Arrange pineapple rings and place a cherry in each center. This will become the top of your cake once flipped.

Step 2: Make the Cake Batter

In a large bowl, cream the butter and granulated sugar together until light and fluffy. Add eggs one at a time, then mix in the vanilla extract. In a separate bowl, whisk flour, baking powder, and salt. Alternately add dry ingredients and milk to the creamed mixture until just combined.

Step 3: Layer and Bake

Carefully pour the batter over the arranged pineapple layer in the pan. Smooth the top with a spatula. Bake at 350°F (175°C) for about 45 minutes or until a toothpick inserted in the center comes out clean.

Step 4: Cool and Flip

Allow the cake to cool in the pan for 10-15 minutes. Then run a knife around the edges and invert onto a serving plate. Let gravity do its magic—lift the pan and admire your glistening masterpiece.

Serving and Storing Your Classic Pineapple Upside Down Cake

This cake is best served slightly warm or at room temperature, when the caramelized fruit is still gooey and fragrant. A scoop of vanilla ice cream or a dollop of whipped cream makes it a show-stopping dessert. For slicing, use a serrated knife to avoid crushing the delicate crumb and fruit topping.

To store, cover the cake tightly with plastic wrap or place in an airtight container. It can sit at room temperature for up to two days or be refrigerated for up to five days. To reheat, a short spin in the microwave brings back that soft, just-baked feel.

Frequently Asked Questions

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

Make sure to grease your pan well, and don’t skip the butter and brown sugar layer—this acts as a nonstick and caramel base.

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works wonderfully. Just be sure to slice it evenly and remove the tough core from each ring.

Is this cake freezer-friendly?

Absolutely. Wrap individual slices or the whole cake tightly and freeze for up to 3 months. Thaw at room temperature or reheat gently.

What if I don’t have a round cake pan?

A square 8×8 inch pan works in a pinch, though your pineapple arrangement may need adjusting.

Can I make this gluten-free?

Yes! Swap the all-purpose flour with your favorite gluten-free baking mix, and ensure other ingredients are labeled gluten-free.

Why did my cake sink in the middle?

Overmixing the batter or underbaking can cause sinking. Make sure to measure ingredients accurately and test doneness with a toothpick.

Want More Pineapple Dessert Ideas?

If pineapple desserts are your thing, you’ll definitely want to check out the 2-Ingredient Pineapple Cake, which offers a super quick bake with big tropical flavor. Another hit is the Moist Apple Crumble Coffee Cake, a fruity bake that balances crumbly and tender textures beautifully.

For something with a creamy twist, try my No-Bake Banana Pudding Cheesecake. Or lean into the cozy comfort of warm fruit bakes with the Slow Cooker Cracker Barrel Fried Apples.

And for a fast and flavorful tropical fix, the 2-Ingredient Pineapple Cake (2nd version) is worth a try—it’s slightly different in texture and ideal for quick prep.