Classic Pineapple Upside Down Cake – A Caramelized, Retro Favorite

This Classic Pineapple Upside Down Cake is the kind of dessert that makes people smile before they even take a bite. It’s buttery, tender, and crowned with glossy pineapple rings and cherries in a brown sugar caramel. The best part?

You don’t need any fancy tools or special skills. If you can melt butter and stir a batter, you’re set. Serve it warm with a scoop of vanilla ice cream, and watch it disappear.

Why This Recipe Works

This recipe balances sweetness with a touch of tang from the pineapple, so it never tastes cloying.

The brown sugar and butter create a quick caramel that keeps the fruit juicy and the top shiny. A sturdy, moist cake batter (made with sour cream and milk) holds up under the fruit without turning soggy. Using canned pineapple ensures consistent texture and moisture, while the reverse-bake method gives you that signature golden topping once inverted.

It’s reliable, forgiving, and consistently bakes up with gorgeous color and flavor.

Shopping List

• Butter: Unsalted, for both the caramel layer and the cake batter
• Brown sugar: Light or dark, for a deeper caramel flavor
• Canned pineapple rings: In juice, not syrup (a 20-ounce can)
• Maraschino cherries: For the classic look and pop of color
• All-purpose flour
• Granulated sugar
• Baking powder
• Salt
• Eggs: Large, room temperature
• Milk: Whole or 2%
• Sour cream: Full-fat for tenderness
• Vanilla extract
• Pineapple juice: Reserved from the can (optional, for extra flavor)

Step-by-Step Instructions

1. Prep the pan: Heat oven to 350°F (175°C). Grease a 9-inch round cake pan (2 inches deep) or a 9-inch cast-iron skillet. Line the bottom with parchment for easy release.
2. Make the caramel layer: Melt 1/4 cup (4 tablespoons) butter.

   Pour into the pan. Sprinkle 1/2 cup packed brown sugar evenly over the butter.

3. Arrange the fruit: Pat pineapple rings dry with paper towels. Lay 6–7 rings over the sugar.

   Place a cherry in the center of each ring, and tuck extras in gaps if you like.

4. Mix dry ingredients: In a bowl, whisk 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt.
5. Cream the butter and sugar: In a separate bowl, beat 1/2 cup (1 stick) softened unsalted butter with 3/4 cup granulated sugar until light and fluffy, about 2 minutes.
6. Add eggs and flavor: Beat in 2 large eggs, one at a time. Mix in 1 teaspoon vanilla extract.
7. Add dairy and dry mix: Stir 1/3 cup sour cream into the batter. Add dry ingredients in two additions, alternating with 1/2 cup milk (and 2 tablespoons pineapple juice if using).

   Mix just until smooth. Do not overmix.

8. Assemble: Spoon batter gently over the fruit. Smooth the top with an offset spatula. The pan will be fairly full—this is normal.
9. Bake: Bake 40–50 minutes, until the top is golden and a toothpick in the center comes out clean or with a few moist crumbs.

   If browning too quickly, tent with foil.

10. Cool briefly and invert: Let the cake rest 10 minutes. Run a knife around the edge. Place a serving plate over the pan and invert carefully.

    Lift the pan and peel off the parchment.

11. Finish and serve: Spoon any caramel left in the pan over the cake. Let it cool at least 15 minutes before slicing. Serve warm or at room temperature.

Storage Instructions

Let the cake cool fully before storing.

Cover and keep at room temperature for up to 2 days. For longer storage, refrigerate up to 5 days, tightly wrapped to prevent drying. Warm slices in the microwave for 10–15 seconds to revive the caramel and soften the crumb.

You can also freeze tightly wrapped slices for up to 2 months; thaw overnight in the fridge and warm before serving.

Health Benefits

• Pineapple provides vitamin C for immune support and manganese for bone health.
• Eggs offer protein and B vitamins, contributing to satiety and energy.
• Portion control matters: A reasonable slice can satisfy a sweet craving without overdoing added sugars.
• Optional swaps: You can reduce sugar slightly in the batter or use part whole-wheat pastry flour for extra fiber, though texture will be denser.

What Not to Do

• Don’t skip drying the pineapple. Excess moisture makes the top watery and the cake soggy.
• Don’t overmix the batter. It toughens the crumb and reduces rise.
• Don’t wait too long to invert. If you cool fully in the pan, the caramel sticks and won’t release cleanly.
• Don’t use a shallow pan. You need a 2-inch-deep 9-inch pan or a skillet to prevent overflow.
• Don’t use pineapple in heavy syrup. It’s too sweet and alters texture; pineapple in juice works best.

Recipe Variations

• Mini cakes: Use a muffin tin with a teaspoon of butter and brown sugar per cup, small pineapple tidbits, and a half cherry. Bake 18–22 minutes.
• Coconut twist: Replace 1/4 cup milk with coconut milk and add 1/2 cup shredded coconut to the batter.
• Rum-kissed: Add 1 tablespoon dark rum to the caramel or batter for a warm, tropical note.
• Gluten-free: Use a 1:1 gluten-free baking flour blend and add an extra tablespoon of milk if the batter seems thick.
• Spiced version: Add 1/2 teaspoon ground cinnamon and a pinch of nutmeg to the dry mix.
• Fresh pineapple: Use thin, well-drained slices; sauté briefly in butter to reduce moisture before assembling.

FAQ

Can I make this cake a day ahead?

Yes. Bake, invert, and let cool.

Wrap tightly and store at room temperature overnight. Warm slices before serving to refresh the caramel.

What if I don’t have sour cream?

Use plain Greek yogurt (full-fat or 2%) in the same amount. It keeps the crumb moist and tender.

How do I prevent the cake from sticking?

Grease well, line the bottom with parchment, and invert after a 10-minute rest.

If the top sticks, rewarm the pan briefly in the oven and try again.

Can I use a springform pan?

It’s not ideal because caramel can leak. If you must, wrap the outside tightly with foil to catch drips and place on a sheet pan.

Why did my cake sink in the middle?

Usually due to underbaking, overmixing, or opening the oven door too early. Bake until fully set and avoid peeking for the first 25 minutes.

Is there a dairy-free option?

Yes.

Use a neutral oil or dairy-free butter, a plant-based milk, and a dairy-free yogurt. Texture will be slightly different but still moist.

Can I reduce the sugar?

You can cut 2–3 tablespoons from the batter without major changes. Keep the caramel layer as written for proper gloss and release.

In Conclusion

Classic Pineapple Upside Down Cake is timeless for a reason.

It’s simple to make, beautiful to serve, and always comforting. With a few smart steps—drying the fruit, not overmixing, and inverting at the right time—you’ll get a tender crumb and a glossy, caramelized top. Keep this recipe in your back pocket for birthdays, potlucks, or any night that needs a little bit of retro charm.