Pineapple Upside-Down Pound Cake

 

The Pineapple Upside-Down Pound Cake is a delightful twist on two beloved classics: the traditional pineapple upside-down cake and the rich, dense pound cake. Combining the caramelized topping of pineapple rings and maraschino cherries with the buttery decadence of a pound cake results in a show-stopping dessert that’s both visually striking and irresistibly flavorful.

First originating in the early 20th century, upside-down cakes gained popularity thanks to the rise of canned fruit and cast-iron skillet baking. Pineapple became the most iconic fruit for this style, and in this recipe, we elevate it with the richness of pound cake, creating a dessert that’s perfect for holidays, potlucks, birthdays, or just a sweet weekend indulgence.

Whether served warm with a dollop of whipped cream or enjoyed chilled with coffee the next morning, Pineapple Upside-Down Pound Cake is a nostalgic dessert with a gourmet touch.

Ingredients

For the Topping:

• ¼ cup unsalted butter (½ stick), melted

• ¾ cup packed light brown sugar

• 7-9 canned pineapple rings, drained

• 7-9 maraschino cherries, stems removed

For the Pound Cake Batter:

• 1 cup (2 sticks) unsalted butter, softened

• 2 ½ cups granulated sugar

• 6 large eggs, room temperature

• 3 cups all-purpose flour

• ½ teaspoon baking powder

• ½ teaspoon salt

• 1 cup sour cream

• ¼ cup whole milk

• 2 teaspoons pure vanilla extract

• Optional: 1 teaspoon almond extract for extra depth

Preparation

Step 1: Prepare the Topping

Preheat your oven to 325°F (163°C). Grease a 10-inch Bundt pan generously with butter or nonstick spray. Pour the melted butter into the bottom of the pan, then evenly sprinkle the brown sugar over it.

Gently place the pineapple rings on top of the sugar layer, arranging them to form a pattern. Place a maraschino cherry in the center of each ring. Set aside while preparing the cake batter.

Step 2: Cream Butter and Sugar

In a large mixing bowl, beat the softened butter and granulated sugar together using an electric mixer on medium speed for 3-5 minutes, until light and fluffy. This creaming step incorporates air into the batter, ensuring a tender texture.

Step 3: Add Eggs

Add the eggs one at a time, beating well after each addition. Scrape down the sides of the bowl to make sure everything is well incorporated.

Step 4: Combine Dry and Wet Ingredients

In a separate bowl, whisk together the flour, baking powder, and salt. In another bowl, mix the sour cream, milk, and vanilla extract (plus almond extract if using).

Add the dry ingredients to the butter mixture in three additions, alternating with the sour cream mixture. Begin and end with the flour. Mix until just combined—do not overbeat.

Step 5: Assemble and Bake

Carefully spoon the batter over the pineapple rings in the Bundt pan. Gently smooth the top. Bake in the preheated oven for 70–80 minutes, or until a toothpick inserted into the center comes out clean.

Let the cake cool in the pan for about 15–20 minutes. Then, place a serving plate on top of the pan and invert quickly and carefully. If any pineapple or cherries stick, gently replace them on the cake.

Variation

• Spiced Version: Add 1 teaspoon cinnamon and ¼ teaspoon nutmeg to the flour mixture for a warm, spiced flavor.

• Boozy Twist: Replace ¼ cup of the milk with dark rum or spiced rum for a tropical adult version.

• Mini Cakes: Use a muffin tin to create individual pineapple upside-down pound cakes—perfect for parties.

• Fresh Pineapple: Use thinly sliced fresh pineapple instead of canned for a more natural sweetness and slight tang.

COOKING Note

• Make sure your ingredients—especially butter, eggs, and sour cream—are at room temperature. This helps ensure a smooth batter and an even rise.

• Grease your Bundt pan thoroughly. Pineapple upside-down cakes have a tendency to stick due to the caramelized topping, so use a nonstick spray with flour or grease with butter and lightly dust with flour.

• If your cake starts to brown too quickly, tent the top with foil after about 50 minutes of baking.

Serving Suggestions

• Serve warm with a scoop of vanilla ice cream or a dollop of freshly whipped cream.

• Drizzle with a rum glaze or caramel sauce for extra decadence.

• Pair with a strong black coffee or a dessert wine like Moscato or Riesling.

Tips

• Drain the pineapple rings and pat them dry to prevent sogginess.

• Use a serrated knife to cut the cake cleanly, especially when serving warm.

• Don’t skip the sour cream—it adds moisture and a slight tang that balances the cake’s sweetness.

• Allow the cake to rest before inverting; this helps the topping set slightly and reduces the chance of it falling apart.

• This cake stores well—cover and refrigerate for up to 5 days. It also freezes well when tightly wrapped in plastic and foil.

Prep Time: 25 minutes

Cooking Time: 75 minutes

Total Time: Approximately 1 hour 40 minutes

Nutritional Information (per slice, based on 12 servings)

• Calories: ~480

• Protein: 5g

• Sodium: 180mg

• Total Fat: 24g

• Saturated Fat: 14g

• Carbohydrates: 60g

• Sugar: 42g

• Fiber: 1g

• Cholesterol: 120mg

FAQs

Can I make this cake in advance?

Yes! It’s even better the next day after the flavors have melded. Store it covered at room temperature for a day or refrigerate for longer freshness.

Can I use a different fruit?

Absolutely. Try peaches, sliced apples, or even cranberries for a seasonal variation. Just make sure the fruit is thinly sliced and not overly juicy.

Why did my cake stick to the pan?

Most likely, the pan wasn’t greased properly or the cake was inverted too early or too late. Be sure to grease thoroughly and allow to cool for 15–20 minutes before flipping.

Can I use a cake mix instead of making it from scratch?

Yes, though you’ll lose some of the rich density of a homemade pound cake. A yellow cake mix or butter cake mix can be used for a quicker version.

Is this cake very sweet?

Yes, it is sweet due to the caramel topping and pineapple. You can reduce the sugar in the batter slightly (to 2 cups instead of 2½) if you prefer a less sweet cake.

Conclusion

The Pineapple Upside-Down Pound Cake is more than just a dessert—it’s a celebration of nostalgic flavors and comforting textures. The golden pineapples and cherries glisten atop a dense, buttery pound cake, making every slice as beautiful as it is delicious. Whether you’re making it for a gathering or a quiet evening treat, this cake offers a crowd-pleasing experience that brings tropical flair and classic comfort together in one glorious dessert.

So preheat your oven, open that can of pineapple, and prepare yourself for a slice of sweet paradise. This is one recipe that deserves a permanent place in your dessert rotation.

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