Name: The Best Pineapple Upside-Down Cake Recipe
Prep time: 15 min
Cook time: 45 min
Total time: 1 h
Cuisine: American
Ingredients: 1/2 cup unsalted butter (1 stick); 1 cup light brown sugar; 20 oz pineapple slices, drained (reserve juice); 8 maraschino cherries; 1 cup all-purpose flour; 1 cup granulated sugar; 2 large eggs; 1 tsp vanilla extract; 1/2 cup milk; 1 1/2 tsp baking powder; 1/4 tsp salt

Jump to Recipe

If you have a soft spot for desserts that bring a nostalgic charm with every bite, then you absolutely must try The Best Pineapple Upside-Down Cake. This cake is a vibrant celebration of juicy pineapple rings caramelized in buttery brown sugar, crowned with bright maraschino cherries, all resting atop a tender, moist cake that feels like a warm hug. It’s more than just a cake; it’s a feel-good dessert that brings sunshine to any table and smiles to faces young and old. Whether it’s a family gathering or a casual afternoon treat, this recipe will quickly become your go-to for a classic that never goes out of style.

The Best Pineapple Upside-Down Cake Recipe - Recipe Image

Ingredients You’ll Need

Each ingredient in this recipe plays a crucial role in delivering the perfect combination of moistness, sweetness, and that irresistible caramelized topping. Don’t let the simple list fool you — these essentials work in harmony to create a dessert that’s truly greater than the sum of its parts.

Unsalted butter (1/2 cup): Provides richness and helps create that luscious caramel base where the brown sugar melts perfectly.
Light brown sugar (1 cup): Brings the deep caramel flavor and moisture to the pineapple topping.
Pineapple slices (20 oz, drained): Adds juicy sweetness and tropical flair, the star of this cake.
Maraschino cherries (8): Offer bursts of color and a subtle sweet contrast to the pineapple.
All-purpose flour (1 cup): The backbone of the cake, creating structure while keeping it tender.
Granulated sugar (1 cup): Sweetens the batter to balance the tartness of pineapple.
Large eggs (2): Bind all the ingredients and add fluffy texture.
Vanilla extract (1 tsp): Enhances aroma and adds a smooth, warm flavor.
Milk (1/2 cup): Moisturizes the batter, ensuring a soft crumb.
Baking powder (1 1/2 tsp): Provides the lift you need for a light, airy cake.
Salt (1/4 tsp): Balances the sweetness and intensifies the flavors.

How to Make The Best Pineapple Upside-Down Cake

Step 1: Prepare the Caramel Base

Start by preheating your oven to 350°F (175°C) so it’s ready the moment your batter is done. Melt the butter gently in a saucepan over medium heat; once completely melted, remove it from the heat and stir in the brown sugar until it’s fully combined and wonderfully sticky. Pour this golden-brown mixture into your 9-inch round cake pan, spreading it evenly to create that signature caramelized crust that will eventually be the crowning glory of your cake.

Step 2: Arrange the Fruit Topping

Lay the pineapple slices right on top of your caramel base, spacing them out evenly to cover the bottom with juicy circles. Nestle a maraschino cherry in the center of each pineapple ring, adding pops of color and sweet flavor that make this cake so visually inviting. This arrangement is not just about looks — it ensures every slice has the perfect harmony of fruit and caramel.

Step 3: Mix the Dry Ingredients

In a mixing bowl, whisk together the flour, granulated sugar, baking powder, and salt. This step might sound straightforward, but it’s key to distributing the leavening agents evenly, which helps your cake rise beautifully with a tender crumb.

Step 4: Combine the Wet Ingredients

In a separate bowl, beat the eggs, vanilla extract, and reserved pineapple juice until smooth and well combined. The pineapple juice is a clever addition that deepens the flavor while adding moisture. Then add the milk and the melted butter to this wet mix, blending everything into a luscious batter ready to meet the dry ingredients.

Step 5: Bring It All Together

Gradually fold the wet ingredients into the dry ingredients, mixing just until everything is incorporated. Be careful not to overmix — a gentle hand here guarantees a soft, tender crumb free of toughness. Slowly pour this batter over your pineapple and caramel layer in the cake pan, spreading it as evenly as possible.

Step 6: Bake and Flip

Bake your cake for 45 minutes, or until a toothpick inserted in the middle comes out clean. Once baked, let it cool in the pan for 10 minutes before carefully inverting it onto a serving plate. This moment of flipping is so satisfying — revealing that glossy, caramel-soaked pineapple masterpiece that is The Best Pineapple Upside-Down Cake.

How to Serve The Best Pineapple Upside-Down Cake

Garnishes

While the cake is gorgeous on its own, a few simple garnishes can elevate the experience. Try a sprinkle of toasted coconut flakes for a tropical twist or a dollop of freshly whipped cream to balance the sweetness. A few fresh mint leaves can provide a lovely pop of color and refresh the palate.

Side Dishes

This cake pairs wonderfully with a scoop of vanilla ice cream or a side of lightly sweetened Greek yogurt for an added creamy texture. If you’re serving it for brunch, a cup of strong coffee or a glass of sparkling wine complements the caramelized pineapple notes beautifully.

Creative Ways to Present

You can serve individual portions topped with a thin slice of caramelized pineapple or construct mini upside-down cakes in ramekins for an impressive presentation. For a fun twist, drizzle warm caramel sauce or a pineapple glaze over the top just before serving to intensify the indulgence.

Make Ahead and Storage

Storing Leftovers

Leftovers of The Best Pineapple Upside-Down Cake can be kept covered at room temperature for up to two days, or refrigerated for up to five days. Make sure to store it in an airtight container to preserve its moisture and prevent the caramel topping from drying out.

Freezing

You can freeze the cake for longer storage by wrapping it tightly in plastic wrap and then aluminum foil to prevent freezer burn. Freeze for up to three months. When ready to enjoy, thaw overnight in the fridge before serving to maintain that moist texture and flavorful topping.

Reheating

To refresh the cake’s warm, melty vibe, reheat slices gently in the microwave for 15-20 seconds or warm the whole cake at 300°F (150°C) for about 10 minutes. This brings back the gooey caramel goodness and soft crumb—just like freshly baked!

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works beautifully and adds a natural brightness. Just be sure to slice it evenly and drain any excess juice to avoid a soggy bottom.

Is it necessary to reserve the pineapple juice?

Reserving the juice is a clever step for boosting flavor and moisture in the batter. You can also substitute it with milk if you prefer, but the juice adds that subtle pineapple essence that makes this recipe so special.

What is the best pan to use for this cake?

A 9-inch round cake pan is ideal for even baking and easy inversion to show off the topping. Avoid using non-stick pans with a teflon coating that might prevent the caramel from releasing cleanly.

Can I make this cake gluten-free?

Yes! Simply swap the all-purpose flour for a gluten-free flour blend that you trust and make sure your baking powder is gluten-free. The texture might be slightly different but still delicious.

How do I prevent the cake from sticking when flipping?

Make sure your pan is well coated with butter before adding the brown sugar mixture. Also, let the cake cool for about 10 minutes after baking before flipping, which helps the caramel set slightly and release more easily.

Final Thoughts

Once you’ve baked and tasted this recipe, you’ll understand why it’s called The Best Pineapple Upside-Down Cake. It’s a timeless classic that marries simplicity with incredible flavor, guaranteed to brighten your day and impress anyone lucky enough to share a slice. So go ahead, gather your ingredients, and make this cake your own sweet tradition. You won’t regret it!

The Best Pineapple Upside-Down Cake Recipe

★★★★★

4.9 from 20 reviews

Author: Ethan
Total Time: 1 hour
Yield: 8 servings 1x
Diet: Vegetarian

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Description

This Pineapple Upside-Down Cake features a caramelized brown sugar and butter base topped with juicy pineapple slices and maraschino cherries. The fluffy vanilla-infused cake bakes on top, then flips over to reveal a glossy, fruity crown. Perfect for a classic dessert that combines moist, sweet cake with tropical flavors and a beautiful presentation.

Instructions

Preheat Oven: Preheat your oven to 350°F (175°C) to ensure it’s at the right temperature when you’re ready to bake the cake.
Prepare Caramel Base: In a saucepan, melt the unsalted butter over medium heat. Once fully melted, remove from heat and stir in the light brown sugar until the mixture is smooth and combined. Pour this caramel mixture evenly into the bottom of a 9-inch round cake pan.
Arrange Pineapple and Cherries: Place the drained pineapple slices neatly on top of the brown sugar mixture in the cake pan. Then, position a maraschino cherry in the center of each pineapple slice for a classic look and added sweetness.
Mix Dry Ingredients: In a mixing bowl, whisk together the all-purpose flour, granulated sugar, baking powder, and salt until they are well combined.
Combine Wet Ingredients: In a separate bowl, beat the eggs with vanilla extract and reserved pineapple juice until smooth. Add the milk and melted butter to this wet mixture and mix thoroughly.
Make Cake Batter: Gradually add the wet ingredient mixture to the bowl with the dry ingredients. Stir gently and mix just until combined to avoid overdeveloping the gluten, which can make the cake tough.
Assemble Cake: Pour the cake batter evenly over the pineapple and brown sugar layers in the cake pan, spreading it out gently with a spatula if needed.
Bake: Place the cake pan in the preheated oven and bake for 45 minutes. Check for doneness by inserting a toothpick in the center; it should come out clean or with a few moist crumbs.
Cool and Invert: Once baked, let the cake cool in the pan for about 10 minutes to set. Then, carefully run a knife around the edges, place a serving plate over the pan, and invert the cake so the pineapple topping is now on top. Serve warm or at room temperature.

Notes

Reserve the juice from the pineapple slices as it adds moisture and flavor to the cake batter.
Be careful when inverting the cake as the topping will be hot and sticky.
Use a non-stick or well-greased cake pan to ensure easy removal of the cake.
For extra flavor, you can sprinkle a little cinnamon or nutmeg into the batter.
Serve with whipped cream or vanilla ice cream for an indulgent dessert.

Prep Time: 15 minutes
Cook Time: 45 minutes
Category: Dessert
Method: Baking
Cuisine: American