Classic Pineapple Upside-Down Cake with Caramelized Pineapple 🍍🍒

Jump to Recipe Print Recipe

Hi, I’m Raya, welcome back to my kitchen! 👋 Today I’m sharing a retro classic that never fails to put a smile on everyone’s face, my pineapple upside down cake. Juicy pineapple rings and sweet cherries bake into a sticky brown sugar caramel, and when you flip the pan, you reveal a beautiful, glossy top over a soft, buttery cake. It is the kind of dessert that looks impressive but is very easy to make, with no special tools and only a handful of simple ingredients. If you have never tried baking an upside-down cake, this is the perfect place to start. Grab a 9-inch pan, and let us make some retro magic together!

Why You’ll Love This Recipe 💕

• Sticky Caramel Topping: Melted butter and brown sugar bake into a glossy caramel under the pineapple, so every bite is sweet and rich.
• Soft, Buttery Crumb: Buttermilk and pineapple juice keep the cake tender, moist, and full of flavor.
• A Showstopper Flip: The moment you turn the cake over and see the pineapple rings is always the best part.
• Simple Pantry Ingredients: Canned pineapple rings, butter, sugar, and flour are all you need.
• Perfect for Any Occasion: It works for Sunday dinners, potlucks, and holidays alike.

Key Ingredients for Pineapple Upside Down Cake 🛒

For the Caramelized Pineapple Topping

• Unsalted Butter (4 tbsp / 57g, melted): Forms the base of the caramel.
• Light Brown Sugar (1/2 cup / 105g, packed): Melts into a sticky, golden glaze.
• Canned Pineapple Rings in Juice (20 oz / 565g, drained): Save 1/4 cup of the juice for the batter.
• Maraschino Cherries (7 to 9): Add a pop of color in the center of each ring.

For the Cake

• All-Purpose Flour (1 1/2 cups / 190g): Gives the cake structure.
• Baking Powder (1 1/2 tsp), Baking Soda (1/4 tsp), Fine Sea Salt (1/2 tsp): For lift and balance.
• Unsalted Butter (1/2 cup / 115g, softened): Makes the crumb rich and tender.
• Granulated Sugar (3/4 cup / 150g): Sweetens the cake.
• Large Eggs (2, room temperature): Add structure and richness.
• Pure Vanilla Extract (1 tsp): Rounds out the flavor.
• Buttermilk (1/2 cup / 120ml, room temperature): Keeps the cake soft and slightly tangy.
• Reserved Pineapple Juice (1/4 cup / 60ml): Adds a tropical flavor and moisture.

Baker’s Note: Blot the pineapple rings with a paper towel before arranging them. Extra moisture can thin out the caramel and make the topping slide. If you love fruity cakes, check out my Strawberry Crunch Cake and my Lemon Blueberry Layer Cake!

Step-by-Step Instructions 👩‍🍳

Step 1: Prepare the Topping

Preheat your oven to 350°F (175°C). Stir the melted butter and brown sugar together and spread the mixture evenly over the bottom of a 9-inch (23 cm) round cake pan that is at least 2 inches (5 cm) deep. Arrange 6 pineapple rings around the edge and 1 in the center, then place a cherry in the middle of each ring and a few extra in the gaps.

Step 2: Mix the Dry Ingredients

Whisk the flour, baking powder, baking soda, and salt together in a medium bowl.

Step 3: Cream the Butter and Sugar

Beat the softened butter and sugar for 3 minutes until pale and fluffy. Add the eggs one at a time, beating well after each, then mix in the vanilla.

Step 4: Finish the Batter

Add the dry ingredients in 3 parts, alternating with the buttermilk and pineapple juice, and mix on low until just combined. Do not overmix, or the cake will turn tough.

Step 5: Bake the Cake

Gently spoon the batter over the pineapple, taking care not to move the rings, and smooth the top. Bake for 40 to 45 minutes, until the cake is golden and a toothpick comes out clean.

Step 6: Flip the Cake

Cool the cake for 5 minutes, then run a thin knife around the edge. Place a serving plate over the pan and flip it over in one confident move. Leave the pan in place for 1 minute so the caramel can drip down, then lift it off. If any fruit sticks, simply place it back on the cake.

Baker’s Tips for Success 💡

• Flip While Warm: Wait only 5 minutes before flipping, because the caramel sets as it cools and will glue the cake to the pan.
• Dry the Pineapple: Patting the rings dry keeps the caramel thick and glossy.
• Use a Deep Enough Pan: A pan that is at least 2 inches deep keeps the caramel from bubbling over in the oven.
• Use Room-Temperature Ingredients: Eggs and buttermilk at room temperature mix evenly for a softer crumb.
• Do Not Overmix: Stop as soon as the flour disappears for a tender cake.

Curious how this classic became so popular? 🍍 King Arthur Baking shares its own pineapple upside-down cake recipe and explains that the cake took off in the early 1900s after a machine was invented to slice pineapple into perfect rings.

How to Serve Pineapple Upside Down Cake 🍽️

Serve the cake warm, cut into wedges, with a scoop of vanilla ice cream or a spoonful of whipped cream. A little extra caramel from the plate is the best finishing touch.

How to Store Pineapple Upside Down Cake 🧊

• At Room Temperature: Keep the cake covered for up to 2 days.
• In the Refrigerator: Store it in an airtight container for up to 5 days. Warm slices for 10 seconds in the microwave before serving.
• In the Freezer: Wrap slices tightly and freeze for up to 2 months. Thaw at room temperature.

Frequently Asked Questions ❓

Can I use fresh pineapple instead of canned?

Yes. Slice fresh pineapple into 1/4-inch (6 mm) rings, pat them very dry, and sauté them in a little butter for 2 to 3 minutes per side to cook off the extra juice. Use 1/4 cup of any pineapple juice in the batter.

Why did my topping stick to the pan?

Usually the cake cooled too long before flipping, or the pan was not coated well with butter and sugar. Flip the cake within 5 minutes and loosen the edges with a knife first.

Can I make this cake in a cast iron skillet?

Yes! Use a 10-inch cast iron skillet, make the topping right in the skillet, and bake for 40 to 45 minutes. Flip it onto a plate just like a regular pan.

Can I skip the cherries?

Of course. The cake tastes just as delicious without them, and you can sprinkle chopped pecans over the caramel instead.