Pineapple Upside Down Cake – Classic, Moist & Caramelized

Pineapple Upside Down Cake delivers a beautiful caramelized fruit topping over a soft, buttery vanilla cake. When you flip the cake after baking, the golden pineapple rings and cherries create a glossy, eye-catching finish that looks impressive yet requires simple ingredients. This classic dessert brings nostalgic flavor and tropical sweetness to any gathering.

Why You’ll Love This Recipe

• Moist, tender cake with caramelized pineapple topping
• Beautiful presentation with minimal effort
• Simple pantry ingredients
• Perfect for holidays and family gatherings
• Balanced sweetness with bright tropical flavor

Ingredients

Topping

• ¼ cup unsalted butter
• ½ cup packed brown sugar
• 1 can (20 ounces) pineapple rings, drained (reserve juice)
• 6 to 8 maraschino cherries

Cake Batter

• 1 ½ cups all-purpose flour
• 1 ½ teaspoons baking powder
• ¼ teaspoon salt
• ½ cup unsalted butter, softened
• ¾ cup granulated sugar
• 2 large eggs
• 1 teaspoon vanilla extract
• ½ cup reserved pineapple juice
• ¼ cup milk

Step-by-Step Instructions

1. Preheat oven to 350°F. Grease a 9-inch round cake pan.
2. Melt ¼ cup butter and pour it evenly into the bottom of the pan.
3. Sprinkle brown sugar evenly over the melted butter.
4. Arrange pineapple rings over the sugar layer. Place cherries in the center of each ring.
5. In a bowl, whisk together flour, baking powder, and salt.
6. In a separate bowl, beat softened butter and granulated sugar until light and fluffy.
7. Add eggs one at a time, mixing well after each addition. Stir in vanilla extract.
8. Alternately add dry ingredients and pineapple juice mixed with milk. Mix until smooth.
9. Pour batter carefully over the pineapple layer and spread evenly.
10. Bake for 40–45 minutes until a toothpick inserted in the center comes out clean.
11. Cool for 10 minutes, then run a knife along the edges.
12. Place a serving plate over the pan and carefully flip the cake. Lift the pan gently.

Tips & Variations

• Use fresh pineapple slices for a brighter flavor
• Add a pinch of cinnamon to the brown sugar for warmth
• Do not skip the cooling time before flipping
• Use a cast iron skillet for deeper caramelization
• Substitute crushed pineapple for a different texture

Storage & Freezer Instructions

• Store covered at room temperature for up to 2 days
• Refrigerate in an airtight container for up to 4 days
• Freeze individual slices wrapped tightly for up to 2 months
• Thaw in the refrigerator overnight before serving
• Warm slightly before serving for best flavor

Serving & Pairing Ideas

• Serve slightly warm with vanilla ice cream
• Add a dollop of whipped cream
• Pair with coffee or tea
• Garnish with extra pineapple slices
• Serve as a holiday or brunch dessert centerpiece

Frequently Asked Questions

Can I make Pineapple Upside Down Cake ahead of time?

Yes. Bake the cake a day in advance and store it covered at room temperature. The flavor deepens as it rests, making it ideal for gatherings.

Why did my topping stick to the pan?

Allow the cake to cool for about 10 minutes before flipping. If you wait too long, the caramel may harden and stick.

Can I use a different pan size?

Yes, but adjust baking time accordingly. A 9-inch pan provides the best thickness and even baking.

Can I reduce the sugar?

You can slightly reduce the granulated sugar in the batter, but keep the brown sugar topping for proper caramelization.

Ready to Make It?

Pineapple Upside Down Cake combines caramelized fruit, buttery cake, and nostalgic charm in every slice. It looks impressive on the table yet uses simple ingredients and straightforward steps. Save this recipe and bake it for your next celebration or cozy weekend treat.

You Might Also Like

• Pineapple Cobbler – Warm tropical fruit baked under a buttery golden topping.
• Strawberry Shortcake Cupcakes – Light vanilla cupcakes filled with fresh strawberries.
• Key Lime Pie Bars – Creamy citrus bars with graham cracker crust.
• Hummingbird Cake – Moist banana and pineapple cake with rich frosting.

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