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, 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 incredibly nostalgic and comforting about a pineapple upside down cake that always brings a smile. This Perfect Pineapple Upside Down Cake Recipe strikes that balance of sweet, buttery caramelized topping and tender cake, making it an absolute joy to share with family or friends.

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 remember the first time I baked this pineapple upside down cake for a Sunday family gathering—everyone kept going back for seconds. It’s not just the flavor; it’s the way the caramelized topping glistens, paired with moist, flavorful cake that never dries out. You really can’t go wrong.

Classic Flavor Combination: The sweet caramelized brown sugar and juicy pineapple rings blend perfectly for that timeless taste.
Simple to Make: This recipe uses pantry staples and canned pineapple, making it super convenient.
Moist and Tender Texture: Sour cream and pineapple juice in the batter keep the cake wonderfully soft.
Great for Any Occasion: Whether it’s a casual weekend treat or a holiday dessert, it fits right in.

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

Every ingredient in this Perfect Pineapple Upside Down Cake Recipe plays its role to build layers of flavor and texture. Here’s why I love these particular choices and some tips to get the best result.

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: Its molasses content gives the topping that rich caramel color and depth of flavor.
Salted Butter: Adds creaminess and enhances the sweetness without needing extra salt.
Canned Pineapple Slices: Convenient and juicy; draining and patting dry prevents sogginess.
Maraschino Cherries: Classic for visual appeal and bursts of sweetness.
All-Purpose Flour: Provides structure while keeping the cake tender.
Baking Powder: Leavens the cake for a light, fluffy crumb.
Salt: Balances the sweetness and enhances flavors.
Unsalted Butter: Creamed with sugars to incorporate air and melt into moistness.
Granulated & Brown Sugar: Both add sweetness with brown sugar adding moisture and flavor.
Egg: Binds ingredients and adds richness.
Sour Cream: Adds moisture and tenderizes the crumb for softness.
Milk & Pineapple Juice: Liquid components that keep the batter smooth and enhance pineapple flavor.

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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 things I enjoy most about the Perfect Pineapple Upside Down Cake Recipe is how easy it is to tweak. I often swap out the cherries for pecan halves to add a lovely crunch, or add a splash of rum to the batter for a subtle tiki vibe.

Variation: Try using fresh pineapple when in season – just slice it thinly and pat dry to avoid sogginess; it adds a wonderful fresh brightness.
Dietary Switch: For a dairy-free version, substitute the butter with coconut oil and use a plant-based yogurt instead of sour cream.
Flavor Boost: A teaspoon of vanilla extract or a sprinkle of cinnamon in the batter gives extra warmth and depth.

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

Step 1: Prepare the Caramelized Topping

Start by heating your oven to 350°F and giving your 9-inch cake pan a good spray with non-stick spray. Mix together the brown sugar and melted salted butter, then spread this mixture evenly across the bottom of the pan. This forms that gorgeous caramelized base you'll flip the cake onto later, so make sure it’s spread well—no empty patches!

Step 2: Arrange the Pineapple and Cherries

Drain your canned pineapple slices and pat them dry with paper towels to avoid extra moisture, which can cause the topping to be soggy. Arrange the slices neatly on top of the sugar-butter base, including a few around the edges for a pretty frame. Tuck the maraschino cherries in the center of the pineapple rings and a few in between — these little pops of red add charm and flavor.

Step 3: Make the Cake Batter

Whisk the flour, baking powder, and salt in one bowl so everything’s evenly combined. In a separate large bowl, beat the softened butter with both sugars for a couple of minutes until fluffy - this step makes a big difference in texture. Then add the egg, sour cream, milk, and reserved pineapple juice, mixing gently until everything is just blended.

Now, fold the dry ingredients into the wet until just combined – don’t overmix or the cake could get tough. Spread the batter gently but evenly over the pineapple and cherries in your pan.

Step 4: Bake and Cool

Bake for about 45-50 minutes until golden brown and a toothpick inserted into the center comes out clean. When done, let the cake cool in the pan for 10-15 minutes — this rest time helps the caramel firm up a little, making it easier to flip without sticking.

Step 5: The Reveal — Flip Your Cake

Place a serving plate or cake stand over the pan, then hold on tight and flip it over in one swift motion. The pineapple and cherries should be perfectly arranged on top, glistening in their caramel glaze. If any pieces stick, use a small knife to carefully loosen them before turning the pan upright again.

Top Tip

After making this cake a dozen times, I’ve realized a few tricks that make your life easier and your cake prettier. These tips will take your Perfect Pineapple Upside Down Cake Recipe from good to unforgettable.

Dry Your Pineapple Thoroughly: Pat your canned pineapple slices dry with paper towels to avoid a watery topping that doesn’t caramelize well.
Don’t Skip the Rest Before Flipping: Allow the cake to cool 10-15 minutes in the pan so the caramel sets and makes flipping a breeze without sticking.
Use Room Temperature Ingredients: Butter, egg, and dairy at room temp mix together more uniformly for a tender batter.
Slow and Steady Mixing: Beat sugars and butter thoroughly but mix flour in gently to keep the cake soft—not dense.

How to Serve Perfect Pineapple Upside Down Cake Recipe

pineapple upside down cake - Serving Suggestion

Garnishes

I love to keep it simple with this cake since it’s already vibrant and flavorful on its own. A light dusting of powdered sugar or a dollop of whipped cream is enough. Sometimes, for extra flair, I add a sprinkle of toasted shredded coconut or a few fresh mint leaves, which add a lovely contrast.

Side Dishes

This cake pairs beautifully with a scoop of vanilla ice cream or a tangy Greek yogurt for balance. If you’re serving a bigger spread, a simple cup of black coffee or lightly brewed tea complements the sweetness perfectly.

Creative Ways to Present

For special occasions, I’ve tried serving this cake layered with fresh whipped cream and pineapple chunks between slices to create a trifle-like dessert. Another fun idea is to cut it into bite-sized squares and serve on a platter with toothpicks for an easy party treat.

Make Ahead and Storage

Storing Leftovers

Leftover pineapple upside down cake keeps well covered tightly at room temperature for about 2 days, but I prefer storing it in an airtight container in the fridge. This helps prolong freshness and keeps the caramel topping from getting sticky.

Freezing

I’ve frozen slices wrapped tightly in plastic wrap and foil, then placed in a freezer bag with great success. Thaw overnight in the fridge and gently warm up in the oven or microwave for that fresh-baked feel.

Reheating

To reheat, I pop slices into a preheated 325°F oven for about 10 minutes, which revives moisture without drying. A quick zap in the microwave works too if you’re in a rush, but watch the time to avoid overheating.

Frequently Asked Questions:

Can I use fresh pineapple instead of canned?

Absolutely! When using fresh pineapple, slice it thinly and pat dry thoroughly to prevent excess moisture in the cake, which can affect caramelizing. Fresh pineapple adds a wonderful bright flavor.

What if my cake sticks when I flip it?

If the cake sticks slightly, don’t worry. Use a knife to gently loosen around the edges and underneath the pineapple before flipping again. Cooling the cake in the pan for 10-15 minutes before flipping makes a big difference in preventing sticking.

Can I make this cake gluten-free?

Yes! Substitute the all-purpose flour with a gluten-free baking blend, ideally one that already contains xanthan gum for structure. Bake as directed, but keep an eye on the texture as some blends absorb moisture differently.

How long will this cake keep fresh?

Stored at room temperature covered, it stays fresh for up to 2 days. Refrigerated in an airtight container, it can last about 4-5 days while maintaining good texture and flavor.

Final Thoughts

The Perfect Pineapple Upside Down Cake Recipe is more than just a dessert to me—it’s a slice of warmth that brings people together. Whether it’s your first time or your hundredth, this cake never disappoints. Give it a try and see how simple ingredients and a little care transform into something truly special.