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This Pineapple Upside Down Cake has a tender, velvety crumb and a buttery vanilla flavor that melts in your mouth. The topping is a gooey caramel dream, crowned with a gorgeous mosaic of golden pineapple rings and bright maraschino cherries. It’s the kind of classic dessert that never disappoints!
This recipe has been a favorite of mine since I was five years old, when my grandma would bake it just for me at our Sunday suppers. Her version used all-purpose flour, but I’ve found that cake flour makes the crumb even lighter and more delicate.
If you love pineapple desserts like this, you’ll also love my Pineapple Sheet Cake, Pineapple Sunshine Cake, or Pineapple Dump Cake. For another classic cake, try my Texas Sheet Cake.
How to Make Pineapple Upside Down Cake (Quick Answer)
- Melt butter + brown sugar in the pan
- Arrange pineapple rings and cherries
- Pour cake batter over the top
- Bake until golden
- Cool 10–15 minutes, then flip
✨ Before You Begin
✨ Dry your pineapple rings: Pat them dry so the topping stays glossy, not soggy.
✨ Choose your pan wisely: Cast iron gives the best caramelization, but a 9-inch cake pan works too.
✨ Room-temperature ingredients: Eggs and buttermilk blend better and create a tender crumb.
✨ Prep for the flip: Invert the cake after 5 minutes of cooling—waiting too long makes the topping stick.
✨ Plan ahead: Assemble the topping the night before, refrigerate, and bake fresh the next day.
Pineapple Upside Down Cake Ingredients + Key Notes
✨ Topping
Brown Sugar: Light or dark brown sugar both work—dark will give a deeper caramel flavor.
Butter: Unsalted butter keeps the caramel topping rich and balanced.
Vanilla: Always go with pure vanilla extract for the best flavor.
Pineapple Slices: Pat them dry thoroughly so the topping stays glossy, not soggy.
💡 Tip: You can also use pineapple chunks or tidbits—just dry them well before layering.
Maraschino Cherries: A classic, festive garnish. No cherries? Try pecan or walnut halves for a fun twist.
✨ Cake
Cake Flour: Creates that velvety, tender crumb. All-purpose works in a pinch, but won’t be quite as soft.
Baking Powder + Baking Soda: A blend of both ensures the cake rises evenly with the perfect texture.
Salt: Enhances all the flavors—don’t skip it.
Butter: Unsalted butter forms the rich base of the batter.
Sugar: Standard granulated sugar.
Eggs: Large, room-temperature eggs mix in more evenly and help the cake rise.
Buttermilk: Well shaken and at room temperature for a light, tangy lift.
Vanilla Extract: Pure vanilla extract deepens the cake’s flavor.
🥣 How to Make Pineapple Upside Down Cake
Here’s a quick look at how to assemble this easy Pineapple Upside Down Cake (full instructions in the recipe card below).
Start by melting the butter in your skillet or cake pan, then sprinkle the brown sugar evenly over the bottom. Arrange the pineapple rings in a single layer and place a cherry in the center of each ring. Pat the fruit dry first so the topping stays glossy and caramelized, not watery.
Next, mix the cake batter until smooth, then gently spread it over the pineapple layer. Bake until the cake is golden and a toothpick inserted in the center comes out clean.
Let the cake cool for 10–15 minutes, then run a knife around the edges and invert it onto a serving plate in one confident motion. Serve warm or at room temperature.
How to Flip Pineapple Upside Down Cake Without Sticking
Flip success is all about timing. Let the cake cool for 10–15 minutes so the caramel topping can settle slightly while still staying warm enough to release from the pan.
Run a knife around the edges to loosen the cake, then place your serving plate over the pan. Hold the plate and pan firmly together, then invert in one confident motion.
Waiting too long can cause the caramel topping to stick, while flipping too soon can make the topping slide. For extra insurance, use a well-greased pan or parchment on the bottom before adding the butter and brown sugar.
⭐ Pro Tips
⭐ Dry the pineapple well
Extra moisture is the #1 reason the topping turns watery instead of glossy and caramelized. Drain the pineapple thoroughly, then pat it dry with paper towels before arranging it in the pan.
⭐ Use the right pan
Cast iron gives the best caramelization, but a standard 9-inch cake pan works too. Just make sure the pan is well greased so the topping releases cleanly.
⭐ Don’t overbake
Bake just until a toothpick inserted in the center comes out clean. Overbaking can dry out the crumb and make the cake less tender.
⭐ Flip at the right time
Let the cake cool for 10–15 minutes, then invert it while the caramel is still warm. Waiting too long can cause the topping to stick.
Light or Dark Brown Sugar for Pineapple Upside Down Cake?
Both work well, but they give slightly different results.
Dark brown sugar creates a deeper, richer caramel flavor and a darker, more dramatic topping. Light brown sugar is milder, a little sweeter, and gives the cake a softer caramel taste.
For that classic, gooey, deeply caramelized finish, dark brown sugar is my favorite—but either one will still give you a beautiful result
Can I Double This Pineapple Upside Down Cake?
Yes! This recipe doubles beautifully and is perfect for feeding a crowd.
Use a 9×13-inch pan to accommodate the larger batch so the topping and batter cook evenly.
Topping Adjustments:
- Butter: Increase to 12 tablespoons (3/4 cup)
- Brown Sugar: Increase to 2 cups (firmly packed)
- Vanilla Extract: Keep at about 1 teaspoon
This will give you a nice, thick, syrupy topping that will create that beautiful, buttery layer under the cake! Because the topping is spread over a larger area, keep an eye on it as it melts to prevent burning and help it cook evenly. Bake until the center is set and a toothpick comes out clean.
Storing + Reheating + Freezing + Make-Ahead Tips
Storing
Cover the cake tightly with plastic wrap or store it in an airtight container. It will stay moist and delicious in the fridge for 3–4 days.
Reheating
For single slices, warm gently in the microwave for 15–20 seconds.
For larger portions, cover with foil and reheat in a 350°F oven for 10–15 minutes. If your cake is in a glass or ceramic dish, let it come to room temperature before placing it in the oven to prevent shattering.
Freezing
Cool the cake completely, then wrap slices in plastic wrap and foil or place them in a freezer bag. Freeze for up to 3 months. Thaw overnight in the fridge, then bring to room temperature or warm gently before serving.
Make-Ahead
You can bake this cake 1–2 days ahead and store it in the fridge. The topping can also be prepared the night before, then refrigerated until you’re ready to bake.
Frequently Asked Questions
◆ Why is my pineapple upside down cake soggy?
Most often, the pineapple wasn’t dried well enough or the cake was underbaked. Pat the pineapple dry before layering, and bake until a toothpick inserted in the center comes out clean.
◆ Can I use pineapple chunks or tidbits instead of rings?
Yes! Pineapple chunks or tidbits work just as well—just dry them thoroughly before using so the topping doesn’t get watery.
ty ◆ Can I bake this without a cast iron skillet?
Definitely. A 9-inch cake pan works too. Prepare the brown sugar topping in a saucepan first, then pour it into the pan before adding the pineapple and batter.
◆ How do I flip the cake without it sticking?
Cool the cake for about 10–15 minutes, then run a knife around the edges. Place a serving plate on top of the pan, hold tightly, and invert in one confident motion. Waiting too long to flip can cause the topping to stick.
◆ Can I make pineapple upside down cake ahead of time?
Yes! Bake it 1–2 days in advance and store it in the fridge. For serving, warm it briefly in the oven, covered with foil, to refresh that gooey topping.
More Fruity Cakes You’ll Love
If your family loves cake as much as mine does, you’ll want to try these fruity favorites next! Each one is a reader-loved recipe, and I can’t wait to hear which becomes your new go-to.
Pig Pickin’ Cake: A classic Southern favorite made with pineapple and mandarin oranges, finished with a light, fluffy frosting.
Cherry Pineapple Dump Cake: Sweet, fruity, and incredibly easy—this one is always a hit for gatherings and potlucks.
Strawberry Jello Cake: Bright, moist, and full of fresh strawberry flavor—an easy, crowd-pleasing dessert.
Blueberry Pound Cake: Rich, buttery, and loaded with juicy blueberries—perfect with coffee or as a simple dessert.
Apple Bundt Cake: Cozy, warmly spiced, and packed with tender apple flavor—great for fall baking.
Tried This Recipe?
If you make this Pineapple Upside Down Cake, I’d love to hear what you think!
⭐ Please leave a rating and a quick comment below — your feedback helps other home cooks and means so much to me!
📱 Quick tip: If you’re on mobile, scroll back up to the recipe card and tap the stars to rate it — super easy!
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Thanks for stopping by my kitchen today — happy cooking, friends! 💕 Kathleen
Pineapple Upside Down Cake
Ingredients
Topping:
- 1 cup brown sugar, firmly packed
- 6 tablespoons butter
- 1/2 teaspoon vanilla extract
- 1 (20-ounce) can pineapple slices, drained
- 15-20 maraschino cherries, stems removed
Cake:
- 1 cup cake flour
- 1 cup all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon baking soda
- 1/4 teaspoon salt
- 1/2 cup butter, softened
- 1 cup sugar
- 2 large eggs at room temperature
- 1 cup buttermilk, well shaken, at room temperature
- 2 teaspoons vanilla extract
Instructions
Make Topping:
- In a 9-inch cast iron pan set over medium heat, melt 6 tablespoons of butter. Add 1 cup of the brown sugar and whisk for about 2 minutes, or until the sugar dissolves and the syrup boils and bubbles. Add vanilla (1/2 teaspoon) after removing it from the heat.
- Pat the pineapple (1 can) very dry between several thicknesses of paper towel and carefully arrange it evenly on the sugar mixture. (Remember skillet is still hot!)
- Add the cherries (15-20) to the inside of the pineapple rings then wherever there’s a gap.
- Adjust oven rack to center position. Preheat the oven to 375°F (191°C).
Make Cake:
- In a medium, mixing bowl, whisk together both flours (1 cup cake flour + 1 cup all-purpose flour), baking powder (1 teaspoon), baking soda (1 teaspoon), and salt (1/4 teaspoon); set aside.
- In a large mixing bowl, using a hand-held electric mixer, cream together butter (1/2 cup) and sugar (1 cup) on medium speed until light and fluffy, about 3 minutes.
- Add eggs (2) one at a time, beating just until the yolk disappears.
- Add the flour mixture and buttermilk (1 cup) alternately, beginning and ending with the flour mixture, with the mixer on low, beating just until combined. Stir in the vanilla (2 teaspoons).
- Gently spoon the batter evenly over the pineapple slices. Bake in preheated oven until golden brown and a toothpick inserted into the center of the cake comes out clean, 35 to 40 minutes.
- Cool the cake in the skillet on a wire rack for 4 minutes only.
- Remove the cake from the oven and cool on a wire rack for 4 minutes. Run a butter knife around the edge of the skillet and, wearing oven mitts and working quickly, invert the cake onto a cake plate, keeping the plate and skillet firmly pressed together.
- Carefully lift the skillet off the cake and replace any fruit stuck to the bottom of the skillet, if necessary. Serve warm or at room temperature.
Fans Also Made:
Notes
- Cast Iron Skillet: The cast iron skillet is perfect to make this type of cake. This recipe starts on the stovetop and then is baked in the oven. Cast iron absorbs heat and holds it, so it’s perfect when you use both types of cooking and baking sources.
- Cake Pan: Yes, you can this cake in a 9-inch cake pan. Make the brown sugar topping in a saucepan, following the instructions above
- Pineapple Chunks: If you’d prefer, or simply happen to have a can of pineapple chunks or tidbits, feel free to use them instead. Follow the instructions for drying the pineapple rings and do so for the chunks.
- Dry The Fruit: drain the pineapples very well.
Nutrition
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I have a 10in cast iron skillet and need to the adjustments in ingredients needed.
My mother used to make hers in a 16in cast skillet but unfortunately I have neither her skillet or recipe! Yours sounds delicious. Anxiously awaiting your reply.
Patrick
Patrick, great question! This recipe is designed for a 9-inch skillet and works perfectly in a 10-inch cast iron skillet as written—no ingredient changes needed.
The only difference is the cake will be just slightly thinner, so I’d start checking it a few minutes early (around 30–32 minutes).
You may also be able to fit an extra pineapple ring or two for a fuller look on top.
I hope you love it—and that it brings back some sweet memories of your mom’s version. 💛
Will serving size of 12 fit into a Bundt cake pan
Hi Terrilynn. I haven’t worked the recipe for a bundt pan. I’m so sorry!
Could this be doubled and baked in a 9×13 pan. If not do you have a from scratch recipe for that. All the recipes I find for that size start with a cake mix, I would rather a from scratch recipe. Thank you.
Hey Nancy. Great question, thanks for asking it! I’ve added all this info to the post.
Pan Size:
You’ll want to use a 9×13-inch baking pan to accommodate the increased batter.
Topping Adjustments:
Butter: Increase the butter to 12 tablespoons (3/4 cup).
Brown Sugar: Increase the brown sugar to 2 cups (firmly packed).
Vanilla Extract: Stick with 1 teaspoon (just slightly more than the original amount for the doubled recipe).
Additional Notes:
The increase in butter and brown sugar will ensure the topping is thick enough to cover the larger surface area of the 9×13-inch pan and still have that rich, caramelized texture.
Monitor the bubbling: Since the topping will be larger and more spread out, keep an eye on the sugar as it melts to prevent burning. Stir it occasionally to help it melt evenly.
This should give you a nice, thick, syrupy topping that will create that beautiful, buttery layer under the cake!
I have a spring form pan…. is this OK? This looks heavenly
Hi Michelle. A spring form pan should work no problem. Just be sure to use the same diameter pan. I hope you enjoy!
I don’t bake that much and I was scared to try this coz I have to flip this cake! My husband loved this!
I wish I could share a photo, it looks so pretty. Thanks for the recipe <3
Oooooh woot woot! I wish I can see the photo. Congrats on your upside down cake 🙂