Pineapple Upside Down Pound Cake

This Pineapple Upside Down Pound Cake combines two Southern dessert favorites into one beautiful cake! It has the rich, buttery texture of a homemade pound cake topped with caramelized brown sugar, juicy pineapple rings, and maraschino cherries.

Instead of baking a traditional pineapple upside-down cake in a standard cake pan, we're making this one pound cake-style in a Bundt pan. The pineapple and cherries bake underneath the batter in a buttery brown sugar mixture, and when you flip the finished cake over-there's your beautiful topping!

It's a showstopper without requiring any frosting or glaze, making it perfect for anytime you're craving an old-fashioned Southern dessert with a pound cake twist.

Why This Recipe Works

- Pound cake base → Buttery and tender yet slices without crumbling.

- Caramelized pineapple topping → Brown sugar and butter melt together for a sweet, glossy finish.

- No special equipment needed → Baked in a standard Bundt pan with pantry staples.

- Tested tips included → From pan prep to release tricks, I've tested this recipe so you can bake it with confidence.

- Step-by-step instructions and video tutorial included.

Recommended tools and equipment:

• Bundt Pan (A 12 cup bundt pan is needed for this recipe.)
• Stand Mixer or Hand Mixer
• Silicone Spatula
• Oven Thermometer
• Cake Keeper
• Measuring Cups and Measuring Spoons

Ingredients You'll Need

Here's a closer look at some of the ingredients that make this Pineapple Upside Down Pound Cake so delicious.

All-purpose flour: Provides structure while giving the pound cake a tender crumb that holds together nicely when sliced.

Unsalted butter: You'll use butter in both the pound cake and the pineapple topping. Make sure the butter for your cake batter is at room temperature.

Granulated sugar: Sweetens the pound cake and works with the butter during the creaming process.

Eggs: Five large room-temperature eggs add richness and structure.

Buttermilk: Adds moisture and a slight tang while helping create a tender pound cake.

Vanilla extract: Enhances the buttery flavor of the cake.

Baking powder: Gives the cake additional lift.

Light brown sugar: Combines with melted butter and pineapple juice to create the caramelized topping.

Pineapple rings: I use canned pineapple rings because they're convenient and easy to arrange in the Bundt pan.

Pineapple juice: A small amount is added to the brown sugar and butter mixture for even more pineapple flavor.

Maraschino cherries: These give us that classic pineapple upside-down cake look and a beautiful pop of color.

Fresh or Canned Pineapple?

I recommend canned pineapple rings in juice for this recipe.

They're convenient, consistently sized, and easy to arrange around the bottom of your Bundt pan. You'll also need a little pineapple juice for the brown sugar topping, so canned pineapple gives you everything you need in one can.

You can use fresh pineapple if you prefer. Just slice it thinly enough to arrange comfortably inside your pan.

A Tip Before Adding Your Pineapple

Drain your pineapple rings well before arranging them in the pan.

You want the pineapple for flavor and moisture, but you don't need a lot of excess juice sitting around the fruit. You'll already be adding the measured amount of pineapple juice called for in the topping.

Bake the Pound Cake

Place the cake on the center rack of your oven and bake at 325°F for approximately 1 hour and 15 minutes.

Remember that ovens bake differently, so use the baking time as a guide rather than relying solely on the clock.

Insert a toothpick or wooden skewer into the thickest portion of the cake. The cake is done when it comes out clean or with a few moist crumbs.

How to Flip Pineapple Upside Down Pound Cake

This is probably the moment that makes everybody nervous. 😂

Once the cake comes out of the oven, allow it to cool in the Bundt pan for approximately 10 minutes. Place a large, flat serving plate over the opening of the Bundt pan. Make sure the plate is large enough to accommodate the entire cake.

Hold the plate firmly against the pan and carefully but quickly flip them over together. Set the plate on a flat surface and gently lift the Bundt pan away from the cake.

The caramelized pineapple and cherries that were at the bottom of your pan are now the beautiful top of your pound cake.

Tips for the Best Pineapple Upside Down Pound Cake

Use room-temperature ingredients. Room-temperature butter, eggs, and buttermilk combine more easily and help create a smoother batter.

Cream the butter and sugar properly. Cream for approximately five minutes to become light and fluffy.

Add your eggs one at a time. Let each egg incorporate before adding the next.

Don't overmix. Once the the butter and sugar is creamed together, mix the remaining ingredients only until combined.

Prepare your Bundt pan thoroughly. This is especially important for an upside-down cake because you want those pineapples to release along with the cake.

Drain the pineapple rings. Excess liquid isn't necessary because you're already adding a measured amount of pineapple juice to the topping.

Don't overbake. A toothpick with a few moist crumbs is perfectly fine.

Don't let the cake sit in the pan indefinitely. You want it to cool enough to become stable, but the caramelized sugar can become stickier as it sits. Your recipe calls for approximately 10 minutes before flipping.

How Do I Keep My Pineapple Upside Down Cake From Sticking?

Proper pan preparation is especially important with this cake.

Generously coat the entire inside of your Bundt pan with baking spray before adding the brown sugar mixture and fruit. Make sure you reach every groove and the center tube.

Once the cake is finished baking, allow it to cool for 10 minutes before flipping it onto your serving plate. Excessive cooling time could potentially cause the cake to stick to the pan.

Can I Use Dark Brown Sugar?

Yes. You can substitute dark brown sugar for the light brown sugar.

Just keep in mind that dark brown sugar contains more molasses, so it will give the topping a deeper flavor and darker appearance.

Can I Use Cake Flour Instead of All-Purpose Flour?

You can, but I recommend all-purpose flour for this recipe.

I like the structure all-purpose flour gives this cake. It creates a tender crumb while still allowing the cake to hold together nicely when sliced.

Cake Flour vs. All Purpose Flour: Which Is Best for Pound Cakes?

How to Store Pineapple Upside Down Pound Cake

Store in an airtight container refridgerated for up to five days. Bring to room temperature before serving.

Frequently Asked Questions

Why did my pineapple topping stick to the pan?

The pan may not have been coated thoroughly enough, or the cake may have remained in the pan too long after baking. Make sure you prepare the pan well and follow the recommended cooling time before removing the cake from the pan.

How do I know when Pineapple Upside Down Pound Cake is done?

Insert a toothpick into the thickest portion of the cake. It's done when the tester comes out clean or with a few moist crumbs.

Can I make this cake ahead of time?

Yes. Pound cake is a great make-ahead dessert. Bake it ahead, allow it to cool completely, and keep it stored in an airtight container refrigerated until you're ready to serve.

Can I leave out the cherries?

Absolutely. The cherries give the cake its classic pineapple upside-down appearance, but you can omit them if you don't like them.

Can I add more pineapple juice to the batter?

I wouldn't. The recipe has been formulated with a specific amount of liquid. Adding extra pineapple juice can change the balance of the batter and affect the texture of your finished pound cake.

Can I use Cake Flour instead of All Purpose flour to bake this cake?

Yes, but I recommend using all-purpose flour. All-purpose flour creates a tender crumb that doesn't fall apart when cutting.

How long do I need to sit my ingredients out to come to room temperature?

That varies by home and by season. Generally it takes about 2-3 hours for ingredients to come to room temperature in my home depending on the season and temperature in my home at the time.

More Dessert Recipes You'll Love

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Have you ever had a pound cake with crushed pineapple? Try my Pineapple Pound Cake recipe.

Creamy Pineapple Parfaits - made with a mixture of yogurt, Cool Whip,
semi-blended pineapple, and are topped with granola clusters.

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