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, reserved from the canned pineapple

Nothing says sweet nostalgia quite like a warm, buttery pineapple cake fresh from the oven. This Perfect Pineapple Upside Down Cake Recipe combines caramelized brown sugar, juicy pineapple, and tender cake in a way that just melts in your mouth. I love making it because it always brings smiles and a little sunshine to the kitchen.

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 tried a few pineapple upside down cakes in my time, but this recipe always shines. It's just the perfect balance of flavors and textures, and it comes together with ingredients you probably already have on hand.

Effortless Elegance: The caramelized topping and pineapple slices make presentation stunning without extra fuss.
Moist & Tender Cake: The combination of sour cream and pineapple juice keeps the crumb just right every time.
Flavor Harmony: The brown sugar and butter topping perfectly complement the tangy pineapple and cherries.
Family-Friendly: This cake never lasts long in my house — it's a guaranteed crowd-pleaser!

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

Every ingredient in the Perfect Pineapple Upside Down Cake Recipe plays a key role — from the buttery topping to the moist cake base. I always make sure to pick good quality canned pineapple and fresh eggs for the best outcome.

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 caramelizes beautifully in the topping for that signature sticky glaze.
Salted butter: Adds richness and balances the sweetness in the topping layer.
Sliced pineapple: Use well-drained pineapple slices so the cake isn’t soggy but stays juicy.
Maraschino cherries: They’re classic here for that pop of color and subtle sweet flavor.
All-purpose flour: Provides structure and a sturdy base to hold up under the topping.
Baking powder: Gives just the right amount of lift to keep the cake light.
Salt: Enhances all the flavors without overpowering.
Unsalted butter: Softened to blend smoothly into the batter, creating tenderness.
Granulated sugar: Sweetens the cake while giving it a fine crumb.
Brown sugar (in batter): Adds subtle molasses notes that deepen the flavor.
Egg: Binds the cake and adds moisture for a soft texture.
Sour cream: Keeps the cake moist and adds a slight tang that pairs wonderfully with pineapple.
Milk: Helps create a smooth, pourable batter.
Pineapple juice: Infuses the cake with extra fruity flavor from the reserved juice.

📝

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 this recipe classic, but there’s room to play around with flavors and add your own twist. Don’t be shy about swapping cherries for fresh raspberries or even adding a dash of cinnamon to the batter.

Variation: Sometimes I sprinkle toasted coconut over the topping before baking — it adds a tropical crunch that’s irresistible.
Dairy-Free: Use coconut or almond milk and vegan butter substitutes for a dairy-free version that still tastes amazing.
Extra Fruity: Adding diced fresh pineapple into the batter gives even more texture and pineapple punch.
Mini Cakes: I’ve made this in muffin tins before for personal-sized treats; just reduce baking time by about 10 minutes.

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 and spraying your 9-inch cake pan with pan spray. Next, melt the butter and stir in the brown sugar to create a sticky, luscious topping. Spread this evenly in the bottom of the pan — it’s the foundation for that irresistible caramel glaze.

Step 2: Arrange the Pineapple and Cherries

Drain the pineapple slices well by pressing them gently between paper towels — you don’t want any excess moisture messing up the topping. Arrange the rings carefully over the brown sugar mixture, placing the maraschino cherries in the center of each pineapple ring and spaces between. This look always makes a stunning visual, and it’s worth taking your time here.

Step 3: Mix the Dry and Wet Ingredients

Whisk together the flour, baking powder, and salt in a bowl — this ensures even leavening. In a separate large bowl, beat the softened butter with both sugars until creamy, about 2–3 minutes. Then add the egg, sour cream, milk, and pineapple juice, mixing just until combined to keep the batter tender.

Step 4: Combine and Bake

Fold the dry ingredients into the wet until smooth but don’t overmix. Pour the batter evenly over the pineapple and spread gently with a spatula. Pop it in the oven for 45-50 minutes, checking doneness with a toothpick. If it comes out clean and the cake is golden on top, you’re good to go.

Step 5: Cool and Flip

Let the cake cool in the pan for 10-15 minutes. This helps the caramel topping set and prevents the fruit from sticking. Then place a serving plate over the pan and flip it carefully in one smooth motion. Voila — that glossy, gorgeous top is now front and center!

Top Tip

Over the years, I’ve learned a few tricks to nailing this cake every time, especially when it comes to the topping and the right moment to flip.

Drain Pineapple Thoroughly: Excess juice can make the cake soggy, so don’t skip the paper towel step.
Don’t Overbake: The cake should be golden but still moist—test with a toothpick after 45 minutes and check every 5 minutes after.
Flip With Confidence: A quick, smooth flip right after cooling prevents sticking and keeps the fruit intact.
Use Room Temperature Ingredients: This helps the batter mix evenly, giving you a better crumb and rise.

How to Serve Perfect Pineapple Upside Down Cake Recipe

pineapple upside down cake - Serving Suggestion

Garnishes

I keep it simple with a dusting of powdered sugar or a dollop of whipped cream. Fresh mint leaves add a pop of color and freshness that pairs beautifully with the sweet caramel and fruit.

Side Dishes

This cake shines best on its own, but if you want to make a dessert platter, a scoop of vanilla ice cream or a light citrus sorbet complements it brilliantly. A cup of strong coffee or chamomile tea rounds out the experience perfectly.

Creative Ways to Present

I once made mini versions in ramekins for a tropical-themed brunch. You could also serve slices on vintage plates with a drizzle of caramel sauce or even layer diced pineapple and cherries inside for a trifle-inspired presentation.

Make Ahead and Storage

Storing Leftovers

I keep leftover cake in an airtight container at room temperature for up to two days — it stays moist and delicious without drying out. If your kitchen is warm, pop it in the fridge wrapped tightly.

Freezing

I’ve frozen slices wrapped in plastic wrap and foil, and they thaw beautifully overnight in the fridge. Just warm gently before serving to bring back that fresh-baked feel.

Reheating

To revive leftover cake, I like to heat individual slices in the microwave for 15-20 seconds or pop them in a warm oven at 300°F for about 10 minutes. It restores the softness and brings out the caramel aroma all over again.

Frequently Asked Questions:

Can I use fresh pineapple instead of canned?

Yes! Fresh pineapple works wonderfully. Just peel, core, and slice it evenly, then pat dry thoroughly with paper towels before arranging in the pan to avoid excess moisture. This can add an extra fresh zing to the cake.

What if I don’t have sour cream on hand?

You can substitute sour cream with plain Greek yogurt or buttermilk. Both bring a similar tangy moisture to the cake. Just maintain the same amount called for in the recipe to keep the texture balanced.

Why is it important to drain the pineapple slices?

Draining pineapple slices removes excess juice that could otherwise make the cake soggy, especially the topping. Pressing slices dry helps the brown sugar and butter caramelize properly and keeps the cake’s texture just right.

How do I prevent the fruit from sticking when flipping the cake?

Make sure to let the cake cool for at least 10 minutes in the pan before flipping. This allows the caramel topping to set slightly. Using a good non-stick spray or greasing the pan well also helps the fruit release easily, making flipping smooth and clean.

Final Thoughts

This Perfect Pineapple Upside Down Cake Recipe is one of those gems I keep coming back to when I want something comforting yet special. Its golden caramel topping and juicy pineapple meet that tender crumb in a way that always wins hearts around my table. Trust me, once you make this, it’ll be your go-to for birthdays, potlucks, or whenever you just need a slice of happiness. Give it a try — I promise you’ll love the results as much as I do!