Pineapple Upside Down Cake

 The Best Pineapple Upside-Down Cake You’ll Ever Make: A Retro Classic That Never Goes Out of Style

There’s something irresistibly nostalgic about Pineapple Upside-Down Cake—its golden caramelized topping, sweet and tangy pineapple rings, and that unmistakable old-fashioned charm that brings everyone back to grandma’s kitchen. This isn’t just a dessert—it’s a showstopper. Whether you’re making it for a Sunday dinner, potluck, or holiday feast, this cake is a guaranteed crowd-pleaser. The moment you flip it out of the pan and reveal that glistening fruit layer, you’ll understand why this dessert stands the test of time.

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Why You'll Love This Pineapple Upside-Down Cake

Perfect blend of sweet and tart from the pineapple and cherries

Moist, rich cake base that’s foolproof thanks to the yellow cake mix

Visually stunning presentation—no frosting required!

Simple ingredients, easy steps, and always delicious results

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Ingredients and Their Roles

First Layer (The Signature Topping)

1 cup light brown sugar – Creates that deep caramel flavor that defines this cake’s top layer.

1 stick butter (melted) – Combines with the sugar to form a rich, gooey glaze that soaks into the cake.

Fruit Topping

1 (20 oz) can sliced pineapples, drained – The classic circular slices make for a beautiful top pattern and a juicy flavor.

1 (20 oz) can crushed pineapple, drained – Adds extra moisture and intense pineapple flavor throughout the cake.

Maraschino cherries – Placed in the center of each ring, these add a pop of color and sweetness.

Cake Base

1 box yellow cake mix – Provides a reliable, fluffy base that pairs perfectly with the fruit topping.

½ cup oil – Keeps the cake moist and tender.

4 eggs – Provide structure and richness, ensuring a light yet satisfying texture.

1 cup pineapple juice (reserved from the canned pineapple) – Enhances the cake mix with a burst of tropical flavor.

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Step-by-Step Instructions

Step 1: Prepare the Pan

Preheat your oven to 350°F (175°C). In a 13x9-inch baking pan, pour the melted butter, then sprinkle the brown sugar evenly over it. Gently stir them together to coat the bottom of the pan in a uniform layer.

Step 2: Add the Fruit

Arrange the pineapple slices over the brown sugar mixture. Place a maraschino cherry in the center of each pineapple ring. Sprinkle crushed pineapple evenly over the top, filling in the gaps. This creates the iconic, glazed fruit topping that becomes the top of the cake after baking.

Step 3: Mix the Cake Batter

In a large bowl, combine the yellow cake mix, oil, eggs, and pineapple juice. Beat until smooth and creamy, about 2–3 minutes on medium speed. Pour the batter gently over the fruit in the pan, spreading evenly.

Step 4: Bake

Place the pan in the oven and bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean. Keep an eye on it—ovens may vary slightly.

Step 5: Cool and Flip

Let the cake rest in the pan for 10 minutes after removing from the oven. Run a knife around the edges to loosen, then carefully invert onto a serving platter. Let gravity work its magic and gently lift off the pan to reveal the stunning caramelized top.

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Why This Recipe Works So Well

This version of Pineapple Upside-Down Cake strikes the perfect balance between ease and elegance. Using cake mix simplifies the baking process, while the use of both sliced and crushed pineapple ensures flavor in every bite. The butter-brown sugar layer turns gooey and golden as it bakes, soaking into the cake for unmatched richness.

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Pro Tips for Pineapple Upside-Down Cake Success

Drain your fruit well to avoid a soggy cake. Save the juice for the batter!

Use parchment paper for extra security when flipping if you're nervous about sticking.

Serve warm or at room temperature—the flavor develops beautifully as it rests.

Add a pinch of cinnamon or nutmeg to the brown sugar mix for a subtle spice twist.

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Serving Suggestions

Serve warm slices with a dollop of whipped cream or a scoop of vanilla bean ice cream.

Pair with coffee or a tropical cocktail like a piña colada for a complete dessert experience.

Make it the centerpiece of a brunch buffet or retro dinner party.

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Final Thoughts: A Tropical Treat That’s Always in Season

This Pineapple Upside-Down Cake recipe proves that classics never go out of style. It’s sweet, sticky, fruity, and completely foolproof—even if you’re not a seasoned baker. With its gorgeous presentation, minimal effort, and rich tropical flavor, it’s a cake that wins hearts at first bite. Tr

y it once, and you’ll be making it for years to come.

Pin it, bake it, love it—and let the compliments roll in.