Pineapple Upside-Down Cake

The smell of brown sugar bubbling in the oven takes me back to my grandmother's kitchen, where she'd hum while arranging pineapple rings with such precision. I remember watching her place each maraschino cherry center like she was setting jewels. There was something magical about that moment of inversion, when she'd count to three and flip the pan, revealing that glistening caramelized topping. Now every time I make this cake, I can almost hear her saying that presentation matters as much as taste.

Last summer I made this cake for my friend's birthday dinner, and I was so nervous about the flip that I made everyone gather around to witness what I called the moment of truth. When the cake released perfectly onto the serving plate, the room erupted in applause before anyone even took a bite. Something about that golden pineapple pattern makes people feel like they're about to eat something special, and the first forkful of warm cake with gooey caramel confirmed it.

Ingredients

• Unsalted butter: Split between the caramel topping and cake batter, butter creates that rich indulgent texture that makes this cake irresistible
• Light brown sugar: The molasses in brown sugar deepens the caramel flavor and creates that signature sticky glaze
• Pineapple rings: Canned pineapple works beautifully here, offering consistent sweetness and tender texture after baking
• Maraschino cherries: These add a pop of color and touch of sweetness that balances the tangy pineapple
• Granulated sugar: Provides sweetness and structure to the vanilla cake layer beneath the fruit
• Eggs: Essential for binding the batter and creating a tender crumb that holds up under the weight of the topping
• Vanilla extract: A touch of vanilla enhances the buttery notes and rounds out the flavors
• All purpose flour: The foundation of the cake, giving it structure while remaining tender
• Baking powder: Ensures the cake rises properly and has a light, fluffy texture
• Salt: A small amount balances the sweetness and enhances all the other flavors
• Whole milk: Adds moisture and richness to the batter for a soft, tender cake

Instructions

Prep your pan and oven:

Preheat your oven to 175°C and generously grease a 23 cm round cake pan with butter or cooking spray

Create the caramel layer:

Melt 60 g butter directly in the bottom of your prepared pan, then sprinkle the brown sugar evenly across the melted butter

Arrange the fruit:

Place pineapple rings over the sugar butter mixture and nestle a maraschino cherry in the center of each ring

Cream the butter and sugar:

In a mixing bowl, beat 120 g softened butter with granulated sugar until light and fluffy, about 3 minutes

Add eggs and vanilla:

Beat in the eggs one at a time, fully incorporating each before adding the next, then stir in the vanilla extract

Mix the dry ingredients:

In a separate bowl, whisk together the flour, baking powder, and salt until well combined

Combine the batter:

Add the flour mixture to the butter mixture in three additions, alternating with the milk, mixing just until combined after each addition

Layer and bake:

Carefully spread the batter over the arranged pineapple and bake for 38 to 42 minutes until golden and a toothpick comes out clean

The crucial flip:

Let the cake cool in the pan for exactly 10 minutes, then run a knife around the edges and invert onto your serving plate

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My daughter helped me make this last weekend, and she was so fascinated by the whole process that she now asks if we can put fruit under every cake we bake. When we served it warm with vanilla ice cream, she declared that the sticky caramel topping was the best part, which is exactly what I thought at her age. Some recipes really do bridge generations.

Make It Your Own

While the classic version is hard to beat, I've discovered that swapping pecans for cherries adds a wonderful nutty crunch that complements the sweet pineapple. You can also try adding a tablespoon of pineapple juice to the batter for extra tropical flavor. Fresh pineapple works beautifully too, just slice it thinly and pat it dry before arranging to prevent excess moisture.

Serving Suggestions

This cake is absolutely divine served still slightly warm, when the caramel is at its gooey best. A dollop of lightly sweetened whipped cream or a scoop of vanilla bean ice cream creates the perfect contrast to the rich, sweet cake. I've also served it with crème fraîche for a slightly tangy counterpoint that cuts through the sweetness beautifully.

Storage and Make Ahead Tips

The cake keeps remarkably well at room temperature for up to two days, covered loosely with foil or stored in an airtight container. The caramel layer stays surprisingly sticky and the cake remains tender. You can also bake it a day before serving, just let it cool completely, cover tightly, and bring it to room temperature before your gathering. If you want to prepare ahead, you can arrange the pineapple and sugar in the pan, cover it, and refrigerate overnight before making the batter the next day.

• Wrap individual slices in plastic and freeze for up to a month
• Reheat gently in the microwave to recreate that just baked warmth
• Leftovers make an incredible breakfast treat with coffee

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There's something deeply satisfying about serving a dessert that looks like it came from a bakery yet came from your own oven. Hope this cake brings as many smiles to your table as it has to mine.

Recipe FAQs

→ How do I know when the cake is done baking?

Insert a toothpick into the center of the cake. If it comes out clean or with just a few moist crumbs, the cake is ready. The top should be golden brown and spring back lightly when touched.

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works wonderfully. Peel and slice fresh pineapple into rings about 1/2 inch thick. You may need to cook it slightly longer to ensure it caramelizes properly in the brown sugar mixture.

→ How long should I wait before inverting the cake?

Let the cake cool in the pan for exactly 10 minutes after removing from the oven. This allows the caramel to set slightly but still be warm enough to release easily. Waiting too long may make it stick to the pan.

→ Can I make this cake ahead of time?

This cake tastes best on the day it's made, but you can bake it up to 24 hours in advance. Store covered at room temperature and serve slightly warmed. The texture remains moist and the flavors stay vibrant.

→ What's the best way to serve pineapple upside-down cake?

Serve warm or at room temperature for the best flavor and texture. It pairs beautifully with whipped cream, vanilla ice cream, or a drizzle of warm caramel sauce. The contrast between the warm cake and cold cream is exceptional.

→ Why did my cake stick to the pan?

This usually happens if the cake cools completely before inverting. Always invert after exactly 10 minutes of cooling. Running a knife around the edges first also helps release it cleanly. Using a well-greased pan prevents sticking issues.