Imagine a dessert that practically glows with nostalgia and sunshine, its crown of golden pineapple rings and jewel-bright cherries gleaming atop a moist, tender cake. This Pineapple Upside Down Cake is more than a recipe—it’s a time-honored celebration of flavor and style, sure to enchant anyone from first bite to last crumb. With its luscious caramel topping, sweet fruit, and buttery homemade crumb, this treat is irresistibly cheerful and sure to be the star at gatherings, family tables, or just when you need a dose of retro delight.

Pineapple Upside Down Cake Recipe - Recipe Image

Ingredients You’ll Need

This Pineapple Upside Down Cake draws on a small cast of grocery staples, each playing a starring role in the final enchantment. Every ingredient brings its own character—moisture, sweetness, color, or the signature tang—so be sure to use them all for the best result.

Unsalted Butter (¼ cup, melted): Gives richness and forms the base for the decadent caramel topping.
Packed Brown Sugar (⅔ cup): Melts into the butter to create that iconic gooey, caramelized layer.
Canned Pineapple Rings (1 can, 20 oz, drained with ¼ cup juice reserved): Offer bright, bold flavor and sunny color—classic for the topping.
Maraschino Cherries (about 10-12): For that pop of color and sweet-tart contrast in every slice.
All-Purpose Flour (1½ cups): The sturdy base for a fluffy but moist crumb.
Granulated Sugar (1 cup): Sweetens and helps with browning and tender texture.
Baking Powder (2 teaspoons): Gives the cake its essential rise—don’t skip it!
Salt (½ teaspoon): Balances sweetness and sharpens every flavor note.
Vegetable Oil (¼ cup): Ensures a moist, tender cake that keeps well.
Milk (1 cup): Adds moisture and a gentle richness to the batter.
Vanilla Extract (1 teaspoon): Brings roundness and warmth to the cake’s flavor.
Large Eggs (2): Bind the batter together and lend lovely structure.

How to Make Pineapple Upside Down Cake

Step 1: Preheat and Prepare Your Oven

Begin by setting your oven to 350°F (175°C) and adjusting the rack so it sits right in the center. This helps the Pineapple Upside Down Cake bake evenly, ensuring that delicate caramel topping doesn’t darken too quickly while the sponge cooks perfectly.

Step 2: Create the Caramel Base

Pour the melted butter into a 9-inch round cake pan, tilting the pan slowly to make sure the butter covers every bit of the bottom. This buttery base is key to an ultra-luxurious, easy-to-release caramel layer.

Step 3: Layer Your Brown Sugar

Sprinkle the packed brown sugar as evenly as possible over the melted butter—not too thick, not too clumpy. This balance lets the sugar melt properly, creating that signature sticky, molten crown the cake is known for.

Step 4: Arrange the Pineapple Rings and Cherries

Set the drained pineapple rings directly onto the sugar/butter mixture in a single, snug layer. Place one ring in the center and nestle the others around it—usually you’ll fit seven. Slide a maraschino cherry into each pineapple ring’s center, and tuck extras in between whenever there’s a gap for playful bursts of color.

Step 5: Mix the Dry Ingredients

Grab a big mixing bowl and whisk together the flour, granulated sugar, baking powder, and salt. This ensures every bite of your Pineapple Upside Down Cake is perfectly light with even crumb throughout.

Step 6: Blend in the Wet Ingredients

Pour the vegetable oil, milk, vanilla extract, and eggs into the dry mixture. Beat on medium speed for about two minutes. The batter should look creamy and smooth, proof you’re on your way to a cloud-like cake!

Step 7: Add the Pineapple Juice

Stir in that reserved ¼ cup of pineapple juice, giving the batter its subtle tropical whisper. It adds both flavor and extra moisture—the real secret behind a craveably tender Pineapple Upside Down Cake.

Step 8: Pour and Bake

Pour your vanilla-scented batter gently over the pineapple rings, doing your best to keep their lovely pattern undisturbed. Smooth the top with a spatula and slide the pan into your preheated oven. Bake for 30 to 35 minutes until golden and a toothpick poked in the center comes out clean.

Step 9: Cool Briefly

Let the cake rest in its pan for five minutes only. This just-right pause allows the caramel to thicken without sticking, making for an easy, gorgeous flip.

Step 10: The Flip

Run a knife around the cake’s edge. Place your chosen serving plate upside down on top of the pan, then—take a breath—firmly flip it over. Let it sit for 30 seconds as gravity (and a bit of magic) helps the cake release. Carefully lift the pan away to reveal the glossy, fruit-studded top.

Step 11: Let It Set

Allow your Pineapple Upside Down Cake to cool at least 15 minutes before slicing. This gives the caramel a chance to set slightly, so every wedge comes out with beautiful pineapple and cherry intact.

How to Serve Pineapple Upside Down Cake

Garnishes

For that extra touch, garnish your Pineapple Upside Down Cake with more maraschino cherries, a sprinkle of toasted coconut, or a dollop of freshly whipped cream. These simple flourishes contrast beautifully against the cake’s buttery richness and make each slice look like a work of art.

Side Dishes

Pair your cake with scoops of creamy vanilla ice cream, a few slices of fresh mango or kiwi, or an assortment of berries. The cool, creamy, or tart accompaniments enhance the cake’s soft texture and amplify the tropical flavors.

Creative Ways to Present

Try slicing and plating each serving individually, or cut the Pineapple Upside Down Cake into wedges and drizzle with a little pineapple juice or caramel sauce. For a retro-vintage look, serve on pastel plates or vintage glassware—or for a picnic, cut into squares and wrap in parchment for grab-and-go fun.

Make Ahead and Storage

Storing Leftovers

Leftover Pineapple Upside Down Cake can be covered tightly and kept at room temperature for a day, or stored in the fridge for up to four days. The flavors mingle and mellow together, so it tastes heavenly even the next morning.

Freezing

To freeze, wrap the cake (once fully cooled) in a double layer of plastic wrap, followed by foil. Store in the freezer for up to three months. Thaw overnight in the fridge before bringing to room temperature for serving.

Reheating

For that just-baked warmth, reheat slices in the microwave for 10–15 seconds, or cover the cake with foil and warm in a low oven (300°F) for about 10 minutes. This revives the caramel and softens the crumb without drying out the cake.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Just slice fresh pineapple into rings of similar thickness and replace them in the recipe. Fresh pineapple may have a bit more juice, which lends extra tang and flavor.

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

You can make this recipe in a square or rectangular pan as long as it’s about 2 inches deep. The presentation will look a little different but will taste every bit as wonderful.

Is it possible to make Pineapple Upside Down Cake ahead of time?

Yes! This cake is actually delicious the day after baking, as the caramel soaks gently into the crumb. Just be sure to keep it covered, and slice just before serving for the best texture.

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

Be generous with the butter base, and don’t rush the short cooling time after baking. Running a thin knife around the pan’s edge before flipping helps release every sugary bit.

Can I use a different fruit for the topping?

Certainly! While Pineapple Upside Down Cake is beloved for its namesake fruit, you can swap in peaches, apples, or plums for a fun twist. Just keep the same brown sugar and butter base for caramel magic.

Final Thoughts

There’s a reason Pineapple Upside Down Cake has stood the test of time—it’s cheerful, rich, and never fails to lift spirits with its retro charm and luscious flavors. Whether you’re an experienced baker or just looking for a fun weekend project, I hope you’ll give this cake a try and share it with someone special. You’ll be hooked on that very first slice!