Why You’ll Love This Recipe

• Visually stunning with a beautiful caramelized pineapple topping
• Incredibly moist and buttery cake crumb
• Uses simple, pantry-staple ingredients
• A classic, crowd-pleasing dessert perfect for any celebration

Equipment You’ll Need

• 9-inch round cake pan (not a springform pan)
• Large mixing bowl
• Medium mixing bowl
• Electric mixer (handheld or stand)
• Whisk
• Rubber spatula
• Wire cooling rack

Ingredients

• For the Topping:
• 1/2 cup unsalted butter, melted
• 1 cup packed light brown sugar
• 1 (20 ounce) can pineapple rings in juice, drained
• 8-10 maraschino cherries, stems removed
• For the Cake:
• 1 1/2 cups all-purpose flour
• 2 teaspoons baking powder
• 1/4 teaspoon salt
• 1/2 cup unsalted butter, at room temperature
• 1 cup granulated sugar
• 2 large eggs, at room temperature
• 1 teaspoon vanilla extract
• 1/2 cup whole milk, at room temperature

Instructions

1. Preheat your oven to 350°F (175°C).
2. For the topping, pour the 1/2 cup of melted butter into a 9-inch round cake pan. Sprinkle the brown sugar evenly over the melted butter.
3. Arrange the drained pineapple rings in a single layer over the brown sugar mixture. Place a maraschino cherry in the center of each pineapple ring and in any gaps.
4. In a medium bowl, whisk together the all-purpose flour, baking powder, and salt. Set aside.
5. In a large mixing bowl, use an electric mixer to beat the 1/2 cup of room temperature butter and granulated sugar together on medium-high speed until light and fluffy, about 3-4 minutes.
6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
7. With the mixer on low speed, add the flour mixture in three parts, alternating with the milk in two parts, beginning and ending with the flour mixture. Mix just until the last streaks of flour disappear. Do not overmix.
8. Carefully spread the cake batter evenly over the pineapple and cherries in the pan.
9. Bake for 45-50 minutes, or until a wooden skewer inserted into the center of the cake comes out clean.
10. Let the cake cool in the pan on a wire rack for exactly 10 minutes. This is the crucial step!
11. Place a large serving plate or cake stand upside down over the cake pan. With oven mitts, carefully and quickly flip the pan and plate together. Lift the pan away to reveal the pineapple topping. If any fruit sticks to the pan, gently lift it off and place it back on the cake.

Expert Cooking Tips

• Pat the pineapple rings dry with a paper towel before placing them in the pan. This prevents the topping from becoming too watery and helps it caramelize beautifully.
• Use room temperature ingredients (butter, eggs, milk) for the cake batter. This helps them emulsify better, creating a smoother, more uniform crumb.
• Don’t overmix the batter once the flour is added. Mix just until combined to ensure a tender, not tough, cake.
• The flip is the most important part! Let the cake cool in the pan for only about 10 minutes. If it cools too much, the caramel will harden and stick to the pan.

Substitutions and Variations

For a tropical twist, you can substitute pineapple juice (reserved from the can) for the milk in the cake batter. If you don’t have maraschino cherries, you can place a pecan half in the center of each pineapple ring. For a gluten-free version, use a high-quality 1-to-1 gluten-free baking flour blend.

Common Mistakes to Avoid

The biggest mistake is letting the cake cool completely in the pan before flipping. The caramel will solidify, and the beautiful topping will stick to the bottom of the pan instead of releasing onto the cake. Another common issue is using a springform pan, which can leak the buttery caramel topping all over your oven; always use a solid, one-piece cake pan.

Serving Suggestions

This cake is absolutely divine served warm, either on its own or with a generous scoop of vanilla bean ice cream or a dollop of fresh, unsweetened whipped cream. The creaminess cuts through the sweetness of the caramel perfectly.

Storage and Reheating Tips

Store any leftover cake covered in the refrigerator for up to 4 days. The caramel topping can make it a bit sticky, so placing parchment paper between slices can help. You can enjoy it cold or gently reheat individual slices in the microwave for 15-20 seconds to restore its warm, gooey texture.

Frequently Asked Questions

Can I use fresh pineapple instead of canned?

Yes, you can! Slice the fresh pineapple into rings about 1/4-inch thick and core them. Pat them very dry before using. Fresh pineapple works beautifully and adds a slightly brighter flavor.

Why did my cake topping stick to the pan?

This usually happens if the cake cools for too long in the pan before inverting. The caramel hardens and acts like glue. Aim to flip the cake about 10 minutes after it comes out of the oven, while it’s still very warm.

Can I make this cake ahead of time?

Absolutely. You can bake it a day in advance. Store it covered in the refrigerator and let it come to room temperature or gently warm it before serving for the best flavor and texture.

My cake batter seems thick. Is that normal?

Yes, the batter for this cake is meant to be quite thick and buttery. This helps it sit on top of the pineapple topping without sinking into it, creating those distinct, beautiful layers.

Conclusion

There’s nothing quite like the moment you flip this cake and reveal the gorgeous, jewel-toned pineapple topping. It’s a timeless dessert that brings so much joy and deliciousness to the table. I hope you and your family love this recipe as much as I do! If you make it, I’d love to see it – please tag me on social media and share your beautiful creation on Pinterest!