Name: Perfect Pineapple Upside Down Cake Recipe
Prep time: 15 min
Cook time: 50 min
Total time: 1 h 5 min
Cuisine: American
Ingredients: ½ cup brown sugar, packed; ¼ cup salted butter, melted; 1 (20-ounce can) sliced pineapple, drained and juice reserved; 12 maraschino cherries; 1 ⅓ cup all-purpose flour; 1 teaspoon baking powder; ½ teaspoon salt; ¼ cup unsalted butter, softened; ½ cup granulated sugar; ¼ cup brown sugar, packed; 1 large egg, room temperature; ¼ cup sour cream; ¼ cup milk; ¼ cup pineapple juice, from reserved pineapple juice

There’s something irresistibly nostalgic and vibrant about a good pineapple upside down cake—it’s that perfect dance of caramelized fruit and tender cake. This Perfect Pineapple Upside Down Cake Recipe has been a favorite of mine for years, delivering just the right balance of sweetness and texture every single time. Let’s dive into why this classic deserves a spot in your baking repertoire.

The image shows a pineapple upside-down cake with a golden brown base layer. On top, there are five bright yellow pineapple rings arranged evenly, each with a shiny red cherry in the center. The pineapple rings have a glistening, caramelized texture, and the cherries are glossy and smooth. One slice of the cake is slightly lifted with a white platter showing beneath. The background surface is a white marbled texture. Photo taken with an iphone --ar 2:3 --v 7

Jump to:

Why You'll Love This Recipe
Ingredients & Why They Work
Make It Your Way
Step-by-Step: How I Make Perfect Pineapple Upside Down Cake Recipe
Top Tip
How to Serve Perfect Pineapple Upside Down Cake Recipe
Make Ahead and Storage
Frequently Asked Questions:
Final Thoughts
Perfect Pineapple Upside Down Cake Recipe

Why You'll Love This Recipe

I can’t say enough about how this recipe lives up to its name. It’s reliable, delightfully sweet without overwhelming, and has that beautiful, glossy pineapple topping that’s just fun to look at and eat. Plus, it’s surprisingly simple to pull off, even if you’re relatively new to baking.

Classic Flavor Combination: The blend of caramelized brown sugar and juicy pineapple hits that sweet-and-tangy spot perfectly every time.
Moist, Tender Cake: Thanks to sour cream and pineapple juice in the batter, this cake stays wonderfully soft and moist.
Easy to Make: You don’t need fancy ingredients or complicated steps—just a few pantry staples and some basic mixing skills.
Impressive Presentation: When flipped, it reveals a glossy pineapple-cherry topping that looks like it belongs in a bakery window.

A round pineapple upside-down cake sits on a white plate with a light speckled edge on a white marbled surface. The top layer features six golden yellow pineapple rings arranged in a circular pattern. Each pineapple ring has a single bright red maraschino cherry in its center. Around and between the pineapple rings are extra dollops of vibrant red cherries embedded in a caramelized brown sugary glaze that covers the top of the cake, giving it a shiny and textured look. The cake beneath the pineapple topping is a moist brown color, visible through the gaps around the fruit. Photo taken with an iphone --ar 2:3 --v 7

Ingredients & Why They Work

Each ingredient in this Perfect Pineapple Upside Down Cake Recipe has a purpose, creating layers of flavor and texture that work in harmony. From the richness of butter to the tang from pineapple juice and sour cream, everything comes together beautifully. Here are a few key things I’ve learned about selecting and handling these ingredients:

Flat lay of bright yellow pineapple slices arranged in a neat pattern, shiny red maraschino cherries placed between the pineapple rings, a small pile of golden brown sugar crystals, a chunk of creamy unsalted butter softly melted, a small mound of white all-purpose flour, a cracked eggshell with a fresh large egg next to it, a splash of smooth sour cream in a dollop, and a small glass of pale yellow pineapple juice, all beautifully arranged on a white marble surface, photo taken with an iphone --ar 2:3 --v 7

Brown Sugar: This is essential for that deep caramel flavor in the topping, plus it adds a subtle molasses note to the cake itself.
Salted Butter: Using salted butter in the topping helps balance the sweetness and enhances the overall flavor.
Sliced Pineapple: Drain it well and blot dry to avoid soggy cake bottoms—fresh pineapple slices could work, but canned makes it easier and consistent.
Maraschino Cherries: These add pops of color and a sweet tartness that complements the pineapple nicely.
All-Purpose Flour: The backbone of the cake structure — make sure it’s fresh and sifted for a lighter texture.
Baking Powder: Provides the rise and keeps the cake fluffy and tender.
Sour Cream: Adds moisture and a slight tang, which balances the sweetness and keeps the crumb soft.
Milk & Pineapple Juice: The pineapple juice, combined with milk, gives extra flavor and keeps the cake moist without weighing it down.
Egg: Helps bind everything and adds richness — make sure it's at room temperature to mix in better.

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Note: You'll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Make It Your Way

One of the best parts about this Perfect Pineapple Upside Down Cake Recipe is how flexible it is. I often tweak it depending on the occasion or what I have in the pantry, and it never disappoints. Feel free to make it your own!

Variation: I’ve swapped out maraschino cherries for fresh raspberries or even halved strawberries when I want a less sugary touch — it adds a nice berry contrast to the pineapple.
Dairy-Free Option: Using coconut yogurt instead of sour cream and a dairy-free milk works beautifully if you want to avoid dairy but keep the moist texture.
Spice It Up: A pinch of cinnamon or nutmeg in the batter gives the cake a lovely warm note that complements the tropical fruit.

Step-by-Step: How I Make Perfect Pineapple Upside Down Cake Recipe

Step 1: Prep Your Pan and Topping

Start by preheating your oven to 350°F (175°C). Spray a 9-inch cake pan generously with pan spray to prevent sticking. Then, mix the brown sugar and melted salted butter until smooth and pour this directly into the bottom of your pan, spreading it out evenly. This sugary base is where the magic begins—it'll caramelize under the cake for that shiny topping.

Step 2: Arrange Pineapple and Cherries

Drain your canned pineapple slices really well—here’s a tip: press them gently between paper towels to soak up extra moisture and avoid soggy cake bottoms. Arrange the pineapple slices in a single layer over the brown sugar mixture, including along the edges for a pretty border. Pop a maraschino cherry in the center of each pineapple ring and in spaces between for those joyful pops of red and sweetness.

Step 3: Make the Batter

Whisk together the flour, baking powder, and salt in a small bowl for even distribution. In a larger bowl, beat together the softened butter with both sugars for 2-3 minutes until you have a creamy, fluffy mix—that’s key for a tender crumb. Add the egg, sour cream, milk, and reserved pineapple juice, and beat just until incorporated. Finally, fold in your dry ingredients—don’t overmix here. The batter will be thick but smooth.

Step 4: Bake It Just Right

Pour the batter gently over your pineapple and cherries in the pan. Spread it evenly with a spatula to cover everything. Bake for 45-50 minutes, watching for a golden top and using a toothpick test: insert it in the center, and if it comes out clean or with just a few crumbs, you're golden. Don’t rush the cooling—let the cake rest for about 10-15 minutes before flipping it out onto a serving plate, so that caramel glaze can set a bit and won't stick.

Top Tip

Over the years making this Perfect Pineapple Upside Down Cake Recipe, I've found a few tricks that really take it to the next level, so here’s what I keep in mind whenever I’m baking it:

Dry the Pineapple Thoroughly: Press the pineapple slices between paper towels to prevent excess moisture from making the cake soggy.
Room Temperature Ingredients: Make sure your butter, eggs, and sour cream aren’t cold, as this helps everything blend smoothly for a better texture.
Don’t Overmix: Once you add the flour mix, stir just enough to combine—it keeps the cake tender, not dense.
Wait to Invert: Let the cake cool in the pan for at least 10-15 minutes before flipping. Too soon, and that gorgeous topping will stick and lose its shine.

How to Serve Perfect Pineapple Upside Down Cake Recipe

pineapple upside down cake - Serving Suggestion

Garnishes

I like keeping it simple with this cake’s natural beauty, but a light dusting of powdered sugar or a dollop of whipped cream brings just the right touch. When I’m feeling festive, a few fresh mint leaves or a small scoop of vanilla ice cream on the side make it feel like a special treat.

Side Dishes

This cake holds its own, but I love pairing it with a cup of strong coffee or a chilled glass of white wine for an afternoon indulgence. For a more casual gathering, fresh fruit salad or a tangy yogurt parfait balances the sweetness nicely.

Creative Ways to Present

For birthday parties or special occasions, I sometimes bake this cake in smaller ramekins for individual servings—it’s as charming as it is delicious. You can also serve it warm with a drizzle of caramel sauce or, for a tropical twist, sprinkle toasted coconut flakes over the top just before serving.

Make Ahead and Storage

Storing Leftovers

Leftover pineapple upside down cake is a delight, believe me! I usually cover it tightly with plastic wrap or store in an airtight container at room temperature for up to two days. After that, I move it to the fridge to keep it fresh for an additional 3 days. Just remember that refrigeration can dry out cakes, so bring it back to room temp before serving.

Freezing

Freezing works well if you want to stash some for later. I wrap individual slices tightly in plastic wrap and place them in a freezer-safe container. When thawing, I let them come to room temperature or warm gently in the microwave for about 20 seconds to bring back that soft, buttery goodness.

Reheating

I find reheating slices in the microwave for a short burst—or warming in a 300°F oven for 10 minutes wrapped loosely in foil—refreshes the cake’s texture and revives the caramel topping's shine. Just keep an eye to prevent over-drying.

Frequently Asked Questions:

Can I use fresh pineapple instead of canned for this recipe?

Absolutely! Fresh pineapple can be used, but be sure to slice it thinly and pat dry to reduce excess moisture, which can affect the cake’s texture and baking time.

Why is it important to let the cake cool before flipping?

Letting the cake cool for about 10-15 minutes allows the caramel topping to set slightly, which helps it release smoothly from the pan without sticking or breaking.

Can I make this cake gluten-free?

Yes! Substitute the all-purpose flour with a gluten-free blend designed for baking, and check that your baking powder is gluten-free to ensure success.

How do I avoid a soggy bottom in this cake?

The key is draining and drying the pineapple slices well and not adding extra liquid beyond what's in the recipe. Also, allowing the cake to cool before flipping prevents sticking and sogginess.

Final Thoughts

This Perfect Pineapple Upside Down Cake Recipe holds a place in my kitchen as the go-to dessert that brings smiles no matter the season. It’s approachable, has that wow factor when you flip it, and best of all, it tastes like a warm hug from old-school baking. I hope you enjoy making it as much as I do—and remember, each cake you bake gets better as you add your personal touch, so have fun with it!