This Pineapple Upside Down Cake Recipe Is the 1950s Glow-Up Your Dessert Table Needs

You know those desserts that make people stop mid-conversation and say, “Wait—what is that?” This is that cake. A glossy, buttery pineapple crown on top, a plush vanilla crumb underneath, and a caramel moat that basically eats like candy. It looks fancy, but spoiler: it’s weeknight-easy and bake-sale legendary.

The best part? You flip it once, and it flips the room’s mood with it.

The Secret Behind This Recipe

The magic is in the topping-to-cake ratio. We’re not skimping on the brown sugar-butter caramel that turns the pineapple into bronzed perfection.

That layer trickles into the cake as it bakes, creating a self-saucing effect that keeps everything ultra-moist without being soggy. We also go with a tender butter cake—lighter than pound cake, sturdier than sponge—so it stands up to the pineapple without flattening out. A touch of sour cream brings tang and structure, while a little pineapple juice amps the flavor and keeps the crumb delicate.

Result: clean slices, juicy top, melt-in-your-mouth base. Chef’s kiss.

Ingredients Breakdown

For the topping:
- 1/2 cup (1 stick/113 g) unsalted butter
- 3/4 cup (150 g) packed light brown sugar
- 8–10 pineapple rings (canned in juice, drained; reserve 1/4 cup juice)
- Maraschino cherries (optional but iconic), 8–12 pieces
- Pinch of fine sea salt
For the cake batter:
- 1 1/2 cups (190 g) all-purpose flour
- 1 1/2 tsp baking powder
- 1/2 tsp fine sea salt
- 1/2 cup (1 stick/113 g) unsalted butter, softened
- 3/4 cup (150 g) granulated sugar
- 2 large eggs, room temperature
- 1 tsp pure vanilla extract
- 1/2 cup (120 g) sour cream, room temperature
- 1/4 cup (60 ml) pineapple juice (from the can)
- Zest of 1/2 lemon (optional, for brightness)

The Method – Instructions

Prep the pan like a pro. Heat oven to 350°F (175°C). Grease a 9-inch round cake pan with a high rim (or a 10-inch cast-iron skillet).
Line the bottom with parchment for guaranteed release.
Make the caramel topping. Melt 1/2 cup butter in a small saucepan over medium heat. Stir in brown sugar and a pinch of salt. Cook 1–2 minutes until glossy and thick, not boiling.
Pour into pan and spread evenly.
Arrange the fruit. Lay pineapple rings over the caramel in a single layer. Nestle cherries into the centers and any gaps. Go full retro—this is the look.
Whisk the dry team. In a bowl, whisk flour, baking powder, and salt.
Set aside.
Cream the butter and sugar. In a large bowl, beat softened butter and granulated sugar until pale and fluffy, 2–3 minutes. This traps air for lift. Don’t rush it.
Add eggs and flavor. Beat in eggs one at a time, scraping the bowl.
Mix in vanilla and lemon zest (if using).
Sour cream and juice, meet dry ingredients. Add half the dry mix, then sour cream, then remaining dry mix. Stir in pineapple juice just until combined. Batter should be smooth but not overmixed.
Load the pan. Spoon batter over the fruit.
Smooth gently to edges. It will be relatively thick—that’s perfect.
Bake. Bake 38–45 minutes until the top is golden and a tester comes out mostly clean (a few moist crumbs are fine). If the top darkens too fast, tent loosely with foil.
Rest, then flip. Cool on a rack 10–15 minutes.
Run a knife around the edge. Invert a serving plate over the pan and flip confidently. If a ring sticks, just lift it out and patch—no one will know.
Serve warm. Slice and serve as-is, or add whipped cream or vanilla ice cream.
Warm cake + cold cream = what happiness tastes like, IMO.

How to Store

Room temp: Cover and keep at room temperature for up to 2 days. The caramel stays soft and the crumb holds up.
Fridge: Store in an airtight container up to 5 days. Bring to room temp or warm slices 10–15 seconds in the microwave to revive the caramel.
Freezer: Wrap slices tightly and freeze up to 2 months.
Thaw overnight in the fridge, then warm gently. FYI, the fruit may release a bit more syrup after freezing—still delicious.

What’s Great About This

Showstopper visuals with low effort. You arrange fruit once and the oven does the glam work.
Balanced sweetness. Brown sugar caramel plus tangy pineapple equals not-cloying, just right.
No special equipment. A standard 9-inch pan or cast-iron skillet gets it done.
Moist crumb that slices clean. Sour cream and pineapple juice keep it tender without falling apart.
Make-ahead friendly. Tastes fantastic on day two, making it party-proof.

Pitfalls to Watch Out For

Runny topping. Don’t add extra juice to the caramel layer. Excess liquid will make the cake soggy, not saucy.
Sticking disaster. Use parchment in the bottom and let it cool 10–15 minutes before flipping.
Too hot and it floods; too cold and it glues.
Dense cake. Cream butter and sugar thoroughly, and don’t overmix once flour goes in. Overmixing knocks out the air you just worked for.
Overbaking. Pull it when a tester shows moist crumbs. Dry cake under juicy pineapple is a plot twist no one wants.
Bland flavor. Salt the caramel lightly and use vanilla plus optional lemon zest.
Tiny tweaks, huge payoff.

Recipe Variations

Rum-spiked. Add 1–2 tbsp dark rum to the caramel off heat and 1 tsp to the batter. Think piña colada, but cake.
Coconut twist. Swap 1/2 cup flour for unsweetened shredded coconut, and use coconut milk instead of pineapple juice for a tropical vibe.
Fresh pineapple. Use ripe fresh slices, patted very dry. Cook time may increase by 3–5 minutes due to higher moisture.
Mini cakes. Divide topping and batter into a 12-cup muffin tin (lined and greased).
Bake 18–22 minutes. Cute, portable, dangerously snackable.
Gluten-free. Use a 1:1 gluten-free baking flour with xanthan gum. Batter may need 1–2 tbsp extra juice to loosen.
Brown butter upgrade. Brown the topping butter until nutty before adding sugar.
It’s an instant depth boost.

FAQ

Can I make this the day before?

Yes. Bake, cool, and store covered at room temp. Rewarm slices slightly before serving to loosen the caramel and refresh the crumb.

Do I have to use cherries?

Nope.

They’re classic and photogenic, but optional. You can fill gaps with chopped pecans, extra pineapple bits, or leave them out entirely.

What if I don’t have sour cream?

Use full-fat Greek yogurt in equal measure. It provides similar tang and structure with a tiny bit less richness.

Can I use a springform pan?

It’s risky.

The caramel can leak. If you must, wrap the base tightly in foil and place on a sheet pan, but a solid pan is safer.

Why did my cake sink in the center?

Common culprits: underbaking, old baking powder, or overmixing. Also, make sure the batter covers the fruit evenly so it bakes uniformly.

How do I prevent a pale top (which becomes the base)?

Bake until deep golden and test for doneness.

Proper caramelization on top equals a flavorful base once flipped.

Can I reduce the sugar?

You can cut 2–3 tablespoons from the batter without drama. Don’t reduce the topping too much or you’ll lose the signature caramel layer.

In Conclusion

This pineapple upside down cake recipe hits the sweet spot between nostalgic and knockout. You get buttery caramel, bright pineapple, and a tender crumb that behaves like it went to finishing school.

It’s simple, reliable, and wildly good-looking—basically the extrovert of cakes. Bake it once, flip it with flair, and consider your dessert reputation upgraded.