Old Fashioned Pineapple Upside Down Cake

Introduction

This Old Fashioned Pineapple Upside Down Cake is a classic homemade dessert with caramelized brown sugar, buttery cake, juicy pineapple slices, and bright maraschino cherries. The cake is baked with the fruit on the bottom, then flipped while warm so the golden pineapple topping becomes the centerpiece.

It’s simple enough for a weekend dessert but special enough for family gatherings, holidays, and celebrations. The reserved pineapple juice also adds extra fruity flavor to the tender cake batter.

Quick Recipe Overview

• Prep Time: 20 minutes
• Bake Time: 40–45 minutes
• Total Time: About 1 hour 10 minutes
• Servings: 10–12
• Course: Dessert
• Cuisine: American

Ingredients

For the Caramel Topping

• ½ cup (1 stick) unsalted butter, melted
• 1 cup packed light brown sugar
• 1 can (20 oz) pineapple slices, juice reserved
• 12–15 maraschino cherries, stems removed

For the Cake Batter

• 2 cups all-purpose flour
• 1¼ cups granulated sugar
• 3 teaspoons baking powder
• ½ teaspoon salt
• ½ cup (1 stick) unsalted butter, softened to room temperature
• 2 large eggs, room temperature
• 1 cup reserved pineapple juice
• 1½ teaspoons vanilla extract

Step-by-Step Instructions

1. Prepare the Oven and Pan

Preheat your oven to 350°F (175°C).

Lightly grease a 9-inch round cake pan or a similar deep baking pan. Place a round piece of parchment paper on the bottom if desired, but make sure the pan is suitable for an upside-down cake.

2. Make the Caramel Topping

Pour the melted butter into the bottom of the prepared pan.

Sprinkle the brown sugar evenly over the melted butter, creating an even layer.

Arrange the pineapple slices over the brown sugar. Place a maraschino cherry in the center of each pineapple ring and add a few cherries between the slices if desired.

3. Mix the Dry Ingredients

In a medium bowl, whisk together the flour, granulated sugar, baking powder, and salt.

4. Make the Cake Batter

In a separate large bowl, beat the softened butter until smooth.

Add the eggs one at a time, mixing after each addition.

Add the vanilla extract and reserved pineapple juice.

Gradually add the dry ingredients and mix just until the batter is smooth and combined.

Avoid overmixing.

5. Assemble the Cake

Carefully spoon the cake batter over the arranged pineapple slices.

Spread the batter gently with a spatula so it covers the fruit evenly.

6. Bake

Bake for 40–45 minutes, or until the center is set and a toothpick inserted into the cake portion comes out clean or with a few moist crumbs.

If the top starts browning too quickly, loosely cover it with foil during the final part of baking.

7. Cool Briefly

Allow the cake to cool in the pan for about 10–15 minutes.

Don’t let it cool completely in the pan because the caramel topping can begin to stick as it sets.

8. Flip the Cake

Place a large serving plate upside down over the cake pan.

Carefully but confidently flip the pan and plate together.

Lift the pan slowly. The caramelized pineapple and cherries should now be beautifully arranged on top of the cake.

If any fruit remains in the pan, gently place it back onto the cake.

Let the cake cool slightly before slicing and serving.

Recipe Tips for Success

• Reserve the pineapple juice: You’ll need 1 cup for the cake batter, so don’t discard it.
• Use room-temperature ingredients: Room-temperature eggs and butter help create a smoother batter.
• Arrange the pineapple carefully: The fruit becomes the visible topping after the cake is flipped.
• Don’t overmix: Mix the batter only until the ingredients are combined.
• Don’t wait too long to flip: Turning the cake out while it’s still warm helps prevent the caramel from sticking.
• Use a sturdy serving plate: The caramel topping can be warm and slightly runny immediately after flipping.
• Flip carefully: Use oven mitts because both the pan and caramel will be hot.

Ingredient Substitutions

Fresh Pineapple

Canned pineapple is convenient and provides juice for the batter. If using fresh pineapple, you’ll need another liquid to replace the reserved pineapple juice.

Maraschino Cherries

The cherries can be omitted if you prefer a simpler pineapple topping.

Unsalted Butter

Salted butter can be used if that’s what you have. If using salted butter, you may want to slightly reduce the added salt.

Light Brown Sugar

Dark brown sugar can be used for a deeper caramel flavor.

Recipe Variations

Pineapple Coconut Cake

Add shredded coconut to the cake batter for a tropical variation.

Pineapple Pecan Cake

Add chopped pecans to the caramel layer for extra crunch.

Mini Pineapple Upside Down Cakes

Divide the pineapple, cherries, caramel, and batter among individual ramekins or muffin-style baking molds and adjust the baking time accordingly.

Extra Pineapple

Add additional small pineapple pieces between the pineapple rings for more fruit in every slice.

Storage and Reheating

Store leftover cake covered in the refrigerator for up to 4 days.

Let slices come closer to room temperature before serving for the best texture.

Individual slices can also be gently warmed in the microwave for a few seconds.

The cake can be frozen, although the pineapple topping may have a slightly different texture after thawing. Wrap individual slices tightly and freeze for up to 2 months.

Serving Suggestions

Serve this pineapple upside down cake:

• Slightly warm
• At room temperature
• With whipped cream
• With vanilla ice cream
• With a cup of coffee
• With black tea

The warm caramelized pineapple pairs especially well with cold vanilla ice cream.

Nutrition Information

Estimated per serving, based on 12 servings:

• Calories: 400 kcal
• Protein: 4 g
• Carbohydrates: 58 g
• Fat: 18 g
• Saturated Fat: 10 g
• Fiber: 1 g
• Sugar: 38 g
• Sodium: 250 mg

Nutrition information is an estimate and can vary depending on the specific ingredients, pineapple syrup, and portion size.

Frequently Asked Questions

Why is it called pineapple upside down cake?

The pineapple and caramel topping are placed in the bottom of the pan before the batter is added. After baking, the entire cake is flipped onto a plate, placing the pineapple topping on top.

Can I use pineapple chunks instead of slices?

Yes. Pineapple chunks can be arranged across the bottom of the pan, although slices create the traditional pineapple upside down cake appearance.

Why did my pineapple upside down cake stick to the pan?

The caramel can become sticky as it cools. Let the cake rest for about 10–15 minutes, then carefully flip it while the topping is still warm.

Can I make this cake ahead of time?

Yes. The cake can be baked several hours ahead or the day before. Keep it covered and refrigerate if storing overnight.

Do I need to refrigerate pineapple upside down cake?

For short-term storage, it can be kept covered at room temperature for a limited period. For longer storage, refrigeration is recommended.

Can I use fresh pineapple?

Yes, but canned pineapple is particularly convenient because the reserved juice is used in the cake batter. With fresh pineapple, you’ll need to provide another liquid for the batter.

How do I know when the cake is done?

Insert a toothpick into the cake portion in the center. It should come out clean or with a few moist crumbs. The cake should also feel set in the center.

Final Thoughts

This Old Fashioned Pineapple Upside Down Cake is a timeless dessert that combines a tender buttery cake with caramelized brown sugar, juicy pineapple, and sweet maraschino cherries.

The best part is turning the cake onto a serving plate and revealing the glossy pineapple topping underneath. It’s a simple baking project with a beautiful presentation that’s sure to bring a classic homemade feel to your dessert table.

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