A glossy Pineapple Upside Down Cake with caramelized pineapple rings and cherries, flipped onto a cake stand, with sticky brown sugar glaze shining on top.
If you want a dessert that feels nostalgic and looks impressive with almost no fuss, this Pineapple Upside Down Cake is it. You get a buttery vanilla cake topped with caramelized brown sugar pineapple that turns into a shiny, sticky glaze when you flip it. Every slice is sweet, juicy, and cozy in the best way.
This pineapple upside down cake is the kind of recipe everyone asks for after the first bite. It’s a true weeknight-friendly bake for when you want something “wow” without a bunch of fancy steps.
Introduction
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Pineapple upside down cake is one of those classic desserts that never goes out of style. You pour a simple batter over a brown sugar pineapple topping, bake it, then flip it to reveal that glossy fruit design. It’s like a little magic trick you can eat.
You’ll love how this pineapple upside down cake tastes like a bakery treat, but it’s made with everyday pantry ingredients. The secret is the brown sugar-butter layer—once it bubbles in the oven, it becomes a caramel sauce that soaks into the fruit and lightly candies the edges.
This is a fan-favorite in so many homes, and for good reason. It’s cozy, kid-approved, and perfect for potlucks, holidays, or an easy weeknight dessert when you want something better than store-bought.
Why You’ll Love This Pineapple Upside Down Cake
- Ultimate comfort dessert: Warm vanilla cake plus caramelized pineapple feels cozy and classic.
- Better than bakery: The topping turns into a sticky glaze that tastes rich and fresh, not overly sweet.
- Easy, no-frosting needed: The fruit topping is the decoration, so you’re done the second you flip it.
- Pantry-friendly ingredients: Basic baking staples, plus canned pineapple, make it simple to shop for.
- Perfect for sharing: It slices neatly for potlucks, holidays, and family dinners.
- Make-ahead friendly: It keeps well, and the flavors get even better the next day.
Ingredients for Pineapple Upside Down Cake
For the caramel pineapple topping
- Unsalted butter (4 tablespoons, melted): Builds the rich caramel base and helps the topping release cleanly.
- Swap: Salted butter works—just keep the cake batter salt modest.
- Light brown sugar (1/2 cup, packed): Creates that sticky, classic caramel flavor and shine.
- Swap: Dark brown sugar for deeper molasses flavor.
- Pineapple rings, canned (7–8 rings, drained well): Gives that signature juicy topping and pretty pattern.
- Swap: Pineapple chunks (drained) for a more rustic look.
- Maraschino cherries (10–12, patted dry): Adds a pop of color and sweet cherry bite.
- Swap: Leave them out, or use extra pineapple pieces.
For the cake batter
- All-purpose flour (1 1/2 cups): The structure of the cake.
- Swap: A 1:1 gluten-free baking blend usually works (texture may be slightly softer).
- Baking powder (2 teaspoons): Helps the cake rise and stay fluffy.
- Fine salt (1/4 teaspoon): Balances sweetness and makes the flavors pop.
- Unsalted butter (6 tablespoons, softened): Makes the crumb tender and buttery.
- Tip: Softened butter (not melted) helps you trap air for a lighter cake.
- Granulated sugar (3/4 cup): Sweetens the cake without overpowering the fruit.
- Eggs (2 large): Adds structure and richness so slices hold together.
- Vanilla extract (2 teaspoons): Brings warm bakery flavor.
- Swap: 1 teaspoon vanilla plus 1/2 teaspoon almond extract for a fun twist.
- Milk (1/2 cup): Keeps the batter smooth and moist.
- Swap: Buttermilk for a slightly tangy, extra-tender crumb.
How to Make Pineapple Upside Down Cake
- 1. Preheat and prep the pan: Heat your oven to 350°F. Lightly grease the sides of a 9-inch round cake pan (not the bottom). This helps the cake edges release without sliding the topping around.
- 2. Build the caramel layer: Pour 4 tablespoons melted butter into the bottom of the pan, then sprinkle the brown sugar evenly over it. Use a spoon to spread it into a smooth layer. Trust me, don’t skip spreading—an even layer means an even glaze.
- 3. Arrange the fruit: Place pineapple rings in a single layer over the brown sugar (usually 7 rings fits nicely). Tuck a cherry into the center of each ring, and add extra cherries between rings if you like. Pat the fruit dry first so the topping doesn’t get watery.
- 4. Mix the dry ingredients: In a medium bowl, whisk together flour, baking powder, and salt for 20 seconds. This little whisk helps the cake rise evenly.
- 5. Cream the butter and sugar: In a large bowl, beat 6 tablespoons softened butter with the granulated sugar for 2–3 minutes, until it looks lighter and fluffy. This step gives you a tender, not-dense crumb.
- 6. Add eggs and vanilla: Beat in the eggs one at a time, scraping the bowl, then mix in vanilla. If the batter looks slightly curdled, it’s okay—it will smooth out once the flour goes in.
- 7. Finish the batter and bake: Add the flour mixture in two additions, alternating with the milk, mixing on low just until combined. Pour the batter over the fruit and gently smooth the top. Bake for 35–45 minutes, until the center springs back lightly and a toothpick comes out with a few moist crumbs.
- 8. Cool and flip with confidence: Cool the cake in the pan for 10 minutes (set a timer). Run a thin knife around the edges, place a plate over the pan, then flip in one quick motion. Lift the pan slowly. If any pineapple sticks, just place it back—no one will know.
Reader Review: I made this pineapple upside down cake for Sunday dinner and the whole pan disappeared. The caramel topping was perfect and the cake stayed super moist even the next day!
Tips for Perfect Pineapple Upside Down Cake
- Drain and dry the pineapple: Extra juice can thin the caramel layer and make the topping slide.
- Spread the brown sugar evenly: Thick spots can burn while thin spots don’t caramelize as well.
- Cream the butter and sugar well: That 2–3 minutes helps the cake bake up fluffy, not heavy.
- Don’t overmix after adding flour: Mix just until you don’t see dry streaks to keep the crumb tender.
- Flip after 10 minutes: Too soon and it can fall apart; too late and the caramel can stick.
- Use a sturdy plate: Choose a plate slightly wider than the pan to catch any drips.
Variations & Substitutions
- Cherry-free version: Skip the cherries and add extra pineapple pieces for a simple look.
- Coconut twist: Add 1/2 cup sweetened shredded coconut to the batter for a tropical vibe.
- Warm spice version: Add 1 teaspoon ground cinnamon to the dry ingredients for cozy flavor.
- Citrus pop: Add 1 tablespoon pineapple juice (from the can) to the batter and reduce milk by 1 tablespoon.
- Lighter dairy swap: Use 2% milk instead of whole milk (still tasty, just a bit less rich).
- Gluten-free option: Use a 1:1 gluten-free baking blend (check that it includes xanthan gum).
- Sheet-pan style: Make it in a 9×13-inch pan; start checking at 30–35 minutes.
- Mini cakes: Use a muffin pan for individual upside-down cakes; bake about 18–22 minutes.
Storing & Reheating
- Fridge: Store covered in the refrigerator for 3–5 days. The topping stays glossy, and the cake stays moist.
- Freezer: Freeze slices for up to 2 months. Wrap each slice tightly in plastic wrap, then place in a freezer bag.
- Thaw: Thaw overnight in the fridge or for a couple hours on the counter.
- Reheat: Warm a slice in the microwave for 10–20 seconds. If the topping looks a little firm, a quick warm-up makes it syrupy again.
Serving Suggestions & Pairings
- A scoop of vanilla ice cream for the classic cozy combo.
- Lightly sweetened whipped cream for a softer finish.
- Hot coffee or black tea for an easy weeknight dessert moment.
- A sprinkle of toasted coconut or chopped pecans for crunch.
- Serve with fresh berries on the side for a bright contrast.
Pineapple Upside Down Cake Recipe Card
Prep Time: 20 minutes
Cook Time: 40 minutes
Total Time: 1 hour (including brief cooling)
Yield: 8 slices
Category: Dessert
Method: Baking
Cuisine: American
Diet: Vegetarian
Ingredients
For the topping
- 4 tablespoons unsalted butter, melted
- 1/2 cup light brown sugar, packed
- 7–8 pineapple rings, canned, drained well
- 10–12 maraschino cherries, patted dry
For the cake
- 1 1/2 cups all-purpose flour
- 2 teaspoons baking powder
- 1/4 teaspoon fine salt
- 6 tablespoons unsalted butter, softened
- 3/4 cup granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 1/2 cup milk
Instructions
- 1. Heat oven to 350°F. Lightly grease the sides of a 9-inch round cake pan.
- 2. Pour melted butter into the pan and sprinkle brown sugar evenly over the bottom.
- 3. Arrange pineapple rings on top of the sugar. Place a cherry in each center and add extra cherries if desired.
- 4. Whisk flour, baking powder, and salt in a bowl.
- 5. Beat softened butter and sugar for 2–3 minutes until fluffy. Beat in eggs one at a time, then vanilla.
- 6. Mix in the dry ingredients in two additions, alternating with milk, just until combined.
- 7. Pour batter over the fruit and smooth the top. Bake 35–45 minutes, until the center springs back lightly.
- 8. Cool 10 minutes, run a knife around the edges, then flip onto a plate. Let cool slightly before slicing.
Notes
- If the cake browns too quickly, loosely tent with foil for the last 10 minutes.
- For clean slices, let it cool 20–30 minutes after flipping.
If you make this pineapple upside down cake, leave a rating and a comment—I love hearing how it turns out for you. Did you keep it classic with cherries, or add your own twist like coconut or cinnamon?
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Pineapple Upside Down Cake (Easy, Buttery, Best Ever)
- Total Time: 55 minute
- Yield: 10 slices 1x
- Diet: Vegetarian
Description
Classic pineapple upside down cake with a caramelized brown sugar topping is buttery, moist, and easy to flip for a bakery-worthy dessert.
Ingredients
Scale
Topping
- 6 tablespoons unsalted butter
- 3/4 cup packed light brown sugar
- 1 (20-ounce) can pineapple slices, drained (reserve 2 tablespoons juice)
- 10 maraschino cherries, drained and patted dry
Cake
- 1 1/2 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/2 teaspoon fine salt
- 1/2 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 1/2 cup whole milk
- 2 tablespoons reserved pineapple juice
Instructions
- Heat oven to 350°F. Grease a 9-inch round cake pan.
- Melt 6 tablespoons butter in pan; sprinkle brown sugar; arrange pineapple and cherries.
- Whisk flour, baking powder, and salt.
- Beat butter and sugar until fluffy; add eggs and vanilla.
- Alternate adding dry ingredients and milk; stir in pineapple juice.
- Spread batter over fruit; bake 35–45 minutes.
- Cool 10 minutes; invert onto a plate; cool before slicing.
Notes
- No maraschino cherries: Swap with drained canned cherries or omit.
- Tools: 9-inch round cake pan, mixer, offset spatula.
- Make-ahead: Bake up to 1 day ahead; re-warm slices to refresh topping.
- Prep Time: 15 minutes
- Cook Time: 40 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American