Pineapple Upside-Down Cake

1 h 15 min | intermediate | vegetarian

Eight squares of pineapple upside-down cake on a white platter, each topped with a glossy pineapple ring and a red maraschino cherry, with caramelized brown-sugar syrup pooling around the golden cake edges.

Published Jan 21, 2026

Prep Time	Cook Time	Total Time
30 min	45 min	1 h 15 min

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Introduction

This classic pineapple upside-down cake bakes up incredibly moist, with caramelized pineapple rings and cherries tucked into every slice.

The buttery brown sugar topping melts into the tender vanilla cake, while a simple honey glaze adds extra shine and tropical flavor.

It’s a make-ahead friendly dessert that’s perfect for holidays, potlucks, or any time you want a nostalgic, crowd-pleasing treat.

Close-up of a slice of pineapple upside-down cake with a glossy pineapple ring and bright red maraschino cherry on top, caramel-brown sugar glaze dripping down the golden cake crumb.

How to Make Pineapple Upside-Down Cake

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Prep the pan and oven

Preheat your oven to 350°F and grease a 9-by-13 inch baking pan lightly.
Pat the pineapple rings dry with paper towels and reserve the can juice for later.
Cook the pineapple topping

Add 3⁄4 cup unsalted butter and 1 cup light brown sugar to a medium saucepan.
Cook over medium heat, stirring often, until the sugar dissolves and the mixture is smooth and bubbling.
Remove from the heat as soon as it looks like a loose caramel and no sugar granules remain.

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Spread topping and arrange fruit

Pour the hot brown sugar mixture into the prepared pan and tilt to coat the bottom evenly.
Arrange the 12 pineapple rings in neat rows over the sugar, fitting them snugly together.
Place one maraschino cherry in the center of each ring, pressing gently into the sugar mixture.
Mix the dry ingredients

In a medium bowl, whisk together the flour, baking powder, baking soda pinch, and salt.
Set this dry mixture aside so it is ready when you begin the batter.
Cream butter and sugar

In a large bowl, beat 3⁄4 cup softened butter with the granulated sugar until light and fluffy.
Use a hand mixer or stand mixer on medium speed for about three minutes for best texture.

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Add eggs and vanilla

Beat in the eggs one at a time, mixing well and scraping the bowl after each addition.
Mix in the vanilla extract just until combined, keeping the mixture smooth and creamy.
Combine wet and dry ingredients

Stir together the milk and 1⁄3 cup reserved pineapple juice in a small measuring cup.
Add one third of the dry ingredients to the butter mixture and mix on low just until combined.
Pour in half the milk mixture and mix briefly, then repeat, ending with the last third of dry ingredients.
Stop mixing as soon as the batter is smooth so the cake stays soft and tender.
Assemble the cake

Carefully spoon the batter over the pineapple topping, then spread it gently to the edges with a spatula.
Try not to disturb the pineapple rings so the top stays pretty after baking.

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Bake the cake

Bake on the center rack for 40 to 45 minutes, until the top is golden and springs back.
A toothpick inserted into the center should come out clean or with a few moist crumbs.
Cool briefly and invert

Place the pan on a wire rack and let the cake rest for 10 to 15 minutes.
Run a thin knife around the edges, then place a large platter over the pan.
Using oven mitts, flip the pan and platter together in one confident motion, then lift the pan off.
Make the honey glaze

While the cake is still warm, add honey, butter, pineapple juice, vanilla, and salt to a small saucepan.
Warm over low heat, stirring, just until the butter melts and the glaze looks smooth and pourable.

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Glaze and serve

Spoon the warm honey glaze slowly over the pineapple and cherries, letting it soak into the cake.
Let the cake cool until just warm, then slice into squares and serve.

Close-up of a square slice of pineapple upside-down cake on a white plate, topped with a glossy pineapple ring and a red maraschino cherry, with caramelized brown sugar glaze dripping down the sides and a few drips of syrup on the plate; a second slice is blurred in the background.

Substitutions

Use fresh pineapple instead of canned rings: Slice fresh pineapple into rings of similar thickness and pat them very dry so the topping still caramelizes nicely without getting watery.
Swap dark brown sugar for light brown sugar: Dark brown sugar gives a deeper molasses flavor and slightly darker color, which makes the topping taste richer and more caramel-like.
Replace milk with canned coconut milk: Full-fat coconut milk adds subtle coconut flavor and extra moisture, giving the cake a soft, almost pudding-like crumb with tropical vibes.

Tips

Dry the fruit well: Extra moisture on the pineapple or cherries can thin the caramel layer, so always blot them carefully with paper towels first.
Keep ingredients at room temperature: Soft butter and room-temperature eggs blend more easily, which traps air in the batter and yields a lighter, fluffier cake.
Do not overcook the caramel base: Once the sugar dissolves and bubbles gently, remove it from the heat to prevent a hard, glassy layer under the fruit.
Invert while the cake is still warm: Flipping after a brief rest helps the topping release cleanly; if it cools fully, the sugar may stick to the pan.
Rotate the pan if needed: If your oven has hot spots, rotate the cake halfway through baking so it browns evenly and bakes at the same rate.
Use a rimmed platter for serving: Choose a serving platter with a small rim to catch any extra glaze or juices and keep the presentation neat.

Nutrition Facts ^*

Energy	557	kcal
Protein	6	g
Total Fat	26	g
Carbohydrates	77	g
Dietary Fiber	1	g

^* Approximate, per serving.
Data source: USDA FoodData Central.

FAQ

Why did my pineapple topping stick to the pan when I flipped it?: Most often the cake cooled too long in the pan before flipping, or the caramel was cooked too hard. Next time, invert after 10 to 15 minutes while the topping is still warm and slightly fluid, and avoid boiling the sugar mixture aggressively.
My cake turned out dense instead of fluffy, what went wrong?: Dense cake usually means the batter was overmixed or the ingredients were too cold. Beat the butter and sugar well at the start, then mix gently once the flour goes in, and always bring eggs, butter, and milk to room temperature before baking.
How do I know when the cake is fully baked?: Look for a golden top that springs back lightly when touched near the center. A toothpick inserted into the middle should come out clean or with a few moist crumbs, but without wet batter clinging to it.
Can I make this pineapple upside-down cake ahead of time?: Yes, you can bake it a day ahead, cool it fully, then cover and refrigerate. Bring it to room temperature before serving, or warm slices gently in the microwave, and add a little extra warm honey drizzle if it seems dry.
Can I bake this in a round pan instead of a rectangular pan?: You can use two 9-inch round cake pans, dividing the topping and batter evenly between them. Check for doneness a little earlier, since smaller pans may bake faster than one large rectangular pan.
What if I do not have reserved pineapple juice?: You can replace the pineapple juice in the batter and glaze with extra milk or even orange juice. Milk keeps the flavor classic and mellow, while orange juice adds a light citrus note that still pairs nicely with pineapple.

Serving Suggestions

This pineapple upside-down cake already brings plenty of nostalgia and color, but a scoop of coconut ice cream makes it downright dreamy.

For a fun adult twist, brush the warm cake lightly with spiced rum before glazing, which adds gentle warmth and deeper tropical flavor.

Leftovers taste amazing the next morning with coffee, especially warmed slightly so the honey glaze loosens and shines again.

Recipe by Eunice.
“I learned to cook by standing in my grandma’s kitchen, watching her turn simple ingredients into meals that fed our entire family. That’s where it started. Today, I create recipes for real life, real kitchens, and anyone who wants good food without overthinking it.” Read more.

Reviews

Rob, San Antonio, TX: Really good and super simple to make 😋 I drizzled a little extra honey glaze on top for more sweetness. — 5 ★

Eunice: Glad it was a hit, Rob!