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 with 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 juice

There’s something irresistibly nostalgic and chewy-sweet about a good pineapple upside down cake. This Perfect Pineapple Upside Down Cake Recipe truly brings that golden, caramelized charm to life, with juicy pineapple rings and cherries baked into a buttery, tender cake. Trust me, it’s worth getting your hands a little sticky for!

The image shows a close-up of a pineapple upside-down cake cut into slices on a white plate. The top layer has five bright yellow pineapple rings, each with a shiny red cherry placed in the middle. The pineapples look soft and caramelized with a glossy, sticky glaze. Below this top fruity layer is a golden-brown, moist cake base with a slightly crumbly texture. The white plate sits on a white marbled surface, and there is a small part of a white bowl with more cherries visible at the top right. 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've baked many versions over the years, but this Perfect Pineapple Upside Down Cake Recipe stands out because it nails that perfect balance of moist cake and rich caramel topping every time. Plus, it’s easier than you’d expect!

Reliable results: The combination of sour cream and pineapple juice keeps the cake moist and flavorful without any fuss.
Classic charm: Pineapple slices and maraschino cherries create that vintage look that everyone loves to dig into.
Simple ingredients: Pantry staples come together beautifully — you probably already have everything needed.
Showstopper dessert: It looks impressive flipped out of the pan, perfect for potlucks or family gatherings.

A round pineapple upside-down cake sits centered on a white plate, presenting six large, golden yellow pineapple rings arranged evenly on top. Each pineapple ring holds a shiny, bright red cherry in its middle, contrasting with the caramelized brown base underneath. In between the pineapple rings, smaller pools of rich red cherry syrup fill the spaces, enhancing the vibrant look. The cake surface is glossy and slightly textured, showing the sticky caramel layer close to the edges. The scene rests on a white marbled surface with a soft, natural light highlighting the warm colors of the dessert. Photo taken with an iphone --ar 2:3 --v 7

Ingredients & Why They Work

Each ingredient here plays its part in delivering the cake’s signature flavor and texture — the brown sugar caramel, the tangy sour cream, the juicy pineapple. Let me walk you through the why behind these choices.

Flat lay of bright yellow pineapple slices neatly arranged next to glossy red maraschino cherries, small piles of light and dark brown sugar crystals, a cube of creamy pale butter, a heap of white all-purpose flour, smooth white sour cream in a dollop, and a small glass of golden pineapple juice, all placed on a white marble surface, photo taken with an iphone --ar 2:3 --v 7

Brown sugar: Packed brown sugar creates that deep, rich caramel flavor for the topping and adds moistness to the cake.
Salted butter: Using salted butter for the topping enhances the caramel’s complexity, while unsalted butter in the batter lets you control salt levels precisely.
Canned pineapple slices: These are perfect because they’re tender with great flavor and the juice can be reserved for added pineapple taste in the cake.
Maraschino cherries: They add that classic pop of color and a little extra sweetness that feels iconic in this dessert.
All-purpose flour: The cake’s base flour ensuring a fine crumb and just the right structure.
Baking powder and salt: Leavening and seasoning balance that keep the cake light but flavorful.
Sour cream: Adds moisture and a subtle tang that pairs beautifully with sweet pineapple.
Milk and pineapple juice: Liquids that hydrate the batter; pineapple juice intensifies the tropical flavor without overpowering.
Egg: Provides structure, binds ingredients, and helps with rise.
Granulated sugar: Sweetens the cake and contributes to tender crumb.

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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

I like to keep the classic vibe for this recipe, but here’s where you can really make it your own. Don’t be afraid to swap the cherries for fresh raspberries or add a touch of coconut flakes on top for a tropical twist.

Variation: Once, I replaced sour cream with Greek yogurt for a slightly tangier, lighter cake, and it was a hit with guests — give it a try!
Dairy-free swap: Use plant-based butter and coconut yogurt to make a dairy-free version — just be sure your milk substitute has a neutral flavor.
Spice it up: Adding a pinch of cinnamon or nutmeg to the cake batter can deepen the flavor and feel especially cozy in cooler months.

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

Step 1: Prep Your Topping Base

Start by preheating your oven to 350°F (175°C). While waiting, mix the brown sugar and melted salted butter, then spread this evenly over the bottom of your greased 9-inch cake pan. This caramel layer is where the magic begins, so make sure it’s smooth and covers all corners evenly.

Step 2: Arrange the Pineapple and Cherries

Drain your pineapple slices well, pat them dry with paper towels to remove any excess moisture — this helps avoid a soggy cake. Then neatly arrange the pineapples on top of the caramel, and tuck maraschino cherries right in the centers and in between the rings. The pattern you create here will be front and center when you flip the cake, so take your time for a pretty result!

Step 3: Whisk the Dry Ingredients

In a separate bowl, whisk together the flour, baking powder, and salt. This ensures your leavening agent is evenly distributed and the cake rises perfectly without any lumps.

Step 4: Cream Butter and Sugars

Beat the softened unsalted butter with granulated sugar and brown sugar until creamy, about 2-3 minutes. Getting this right adds a tender crumb and helps the cake set just right. Don’t rush — the mixture should look fluffy and light.

Step 5: Add Wet Ingredients and Combine

Beat in the egg, sour cream, milk, and pineapple juice. Once everything looks just combined, fold in the dry ingredients gently. Mixing too much here can make the cake tough, so stop as soon as you see no flour.

Step 6: Bake and Flip

Pour the batter evenly over your pineapple arrangement and bake for 45-50 minutes. To check doneness, insert a toothpick in the center — it should come out clean or with just a few moist crumbs. Let it cool for about 10-15 minutes, then invert it onto your serving plate. This bit always gets me excited — watch that glossy caramel, pineapples, and cherries shine!

Top Tip

Having made this Perfect Pineapple Upside Down Cake Recipe countless times, I’ve learned some tips that really make the difference between good and unforgettable:

Dry the Pineapple Slices: Patting the pineapple dry ensures the caramel topping stays thick and doesn’t turn watery while baking.
Don’t Overmix Batter: Mixing just until combined keeps the cake tender and soft — overmixing develops gluten and makes it dense.
Let the Cake Rest Before Flipping: Waiting 10-15 minutes allows the caramel to harden just enough to release cleanly without sticking or tearing.
Use a Non-Stick Pan or Proper Greasing: This prevents the caramel from sticking, making your flip easy and flawless.

How to Serve Perfect Pineapple Upside Down Cake Recipe

pineapple upside down cake - Serving Suggestion

Garnishes

I usually keep it simple with a light dusting of powdered sugar or a few fresh mint leaves for color. Sometimes a dollop of whipped cream gives it that creamy contrast to the sticky sweetness.

Side Dishes

This cake loves being paired with fresh fruit salads or a scoop of vanilla bean ice cream. I’ve also served it alongside a cup of cinnamon-spiced tea or fresh brewed coffee, perfect for weekend brunch vibes.

Creative Ways to Present

For special occasions, I like to make mini versions in muffin tins, arranging pineapple wedges and cherries just like the big cake. They’re perfect for parties and look adorable on a dessert tray. You could also drizzle warm caramel sauce or even sprinkle toasted coconut on top.

Make Ahead and Storage

Storing Leftovers

I wrap leftover cake tightly in plastic wrap and keep it at room temperature for up to 2 days, or refrigerate for up to 5 days. Just bring it back to room temp before serving for best texture and flavor.

Freezing

Yes, this cake freezes beautifully! I wrap individual slices tightly in plastic wrap then foil, so I can thaw just what I need. Thaw in the fridge overnight and warm slightly before serving for that fresh-baked vibe.

Reheating

To keep the cake moist, I warm slices gently in a microwave for about 15-20 seconds or pop them into a low oven (300°F) wrapped in foil for 10 minutes. This revives the caramel’s gooey texture wonderfully.

Frequently Asked Questions:

Can I use fresh pineapple instead of canned?

Fresh pineapple can be used, but you’ll want to slice it thin and caramelize it gently first to remove excess moisture and achieve the right texture. Canned pineapple is softer and more consistent for this cake.

What if I don’t have maraschino cherries?

You can substitute with fresh cherries or even dried cranberries for a different look and flavor, though the classic red pop of maraschino cherries is what gives this cake its signature appearance.

How do I prevent the cake from sticking when I flip it?

Using a generous coating of melted butter and brown sugar for the topping and making sure your pan is well greased help prevent sticking. Also, let the cake cool for around 10-15 minutes before flipping to let the caramel set slightly, ensuring a clean release.

Can I make this cake in a different size pan?

You can adjust the size but keep in mind baking time will vary. For larger pans, the cake might bake faster on the edges so test with a toothpick earlier. For smaller pans, increase baking time. I find a 9-inch pan strikes the perfect balance.

Final Thoughts

This Perfect Pineapple Upside Down Cake Recipe holds a special place in my kitchen memories — it’s the dessert I bring to family gatherings and the one that gets asked for again and again. It’s approachable, forgiving, and always delights with its caramelized goodness. I can’t wait for you to try it out and see how it becomes your go-to nostalgic treat.