Pineapple Upside-Down Cake

Pineapple Upside-Down Cake is a retro classic that never goes out of style. With its sticky-sweet caramelized pineapple topping and rich buttery cake, this dessert delivers a beautiful presentation right out of the pan. Every slice is a perfect balance of fruity brightness and cozy cake comfort.

Behind the Recipe

There’s something nostalgic and joyful about flipping a cake and revealing that golden layer of pineapple and cherries. This was one of the first cakes I ever baked with my grandmother. I remember the thrill of seeing that glossy fruit topping after flipping the pan—it felt like magic. Now, it’s my go-to dessert when I want to bring a touch of vintage charm and tropical flavor to the table.

Recipe Origin or Trivia

The Pineapple Upside-Down Cake became wildly popular in the United States during the 1920s when canned pineapple first became widely available. Dole held a recipe contest, and this cake was one of the standout stars. Its signature look—pineapple rings and maraschino cherries—is instantly recognizable and part of what’s made it a beloved American dessert for generations.

Why You’ll Love Pineapple Upside-Down Cake

This cake is more than just pretty to look at. Here’s why you’ll want to make it again and again:

Versatile: Perfect for birthdays, potlucks, brunch, or an easy weekend bake.

Budget-Friendly: Uses pantry staples and affordable canned pineapple.

Quick and Easy: No fancy tools or frosting needed.

Customizable: Switch up the fruit or add spices for your own twist.

Crowd-Pleasing: Everyone loves the sweet, sticky topping and moist cake.

Make-Ahead Friendly: Keeps well and tastes even better the next day.

Great for Leftovers: Enjoy a slice with coffee or as a sweet breakfast treat.

Chef’s Pro Tips for Perfect Results

This cake is simple but there are a few secrets to making it sing:

1. Use room temperature ingredients so your batter mixes evenly and bakes light.
2. Dry the pineapple slices slightly with paper towels to avoid excess moisture.
3. Melt the butter and brown sugar first for a deeper, richer caramel layer.
4. Don’t overmix the batter—just combine until smooth for a tender crumb.
5. Let it rest for 5–10 minutes before flipping so the topping stays in place but doesn’t stick.

Kitchen Tools You’ll Need

You don’t need much to pull this off:

9-Inch Round Cake Pan: The perfect size for the classic presentation.

Mixing Bowls: For wet and dry ingredients.

Whisk and Spatula: For mixing without overworking the batter.

Electric Mixer (optional): For creaming butter and sugar faster.

Cake Server or Plate: For flipping and serving.

Ingredients in Pineapple Upside-Down Cake

Here’s everything you need to make this golden beauty shine:

1. Canned Pineapple Rings: 1 can (20 oz) – Sweet, juicy slices for the top (and bottom!) of the cake.
2. Maraschino Cherries: 6–8 – Nestled in each pineapple ring for color and sweetness.
3. Brown Sugar: ½ cup – Caramelizes to create that sticky, flavorful topping.
4. Unsalted Butter: ½ cup (1 stick), divided – Half for the topping, half for the cake batter.
5. Granulated Sugar: ¾ cup – Adds sweetness and helps with that golden crumb.
6. Eggs: 2 large – Binds the batter and adds richness.
7. All-Purpose Flour: 1 ½ cups – The foundation of the cake structure.
8. Baking Powder: 2 teaspoons – Gives the cake a light, fluffy rise.
9. Salt: ¼ teaspoon – Balances the sweetness.
10. Whole Milk: ½ cup – Adds moisture and tenderness.
11. Vanilla Extract: 1 teaspoon – Rounds out the flavor.

Ingredient Substitutions

Short on something? Here are some easy swaps:

Canned Pineapple Rings: Use fresh pineapple slices, just slice thinly.

Maraschino Cherries: Try fresh cherries, raspberries, or omit if preferred.

Brown Sugar: Coconut sugar adds a slightly different caramel flavor.

Whole Milk: Use almond, oat, or 2% milk instead.

Butter: Margarine or plant-based butter works for dairy-free versions.

Ingredient Spotlight

Brown Sugar: It’s not just sweet—it creates that syrupy, sticky caramel layer when baked with butter and fruit.

Pineapple: The fruit caramelizes beautifully and adds a bright acidity that cuts through the richness of the cake.

Instructions for Making Pineapple Upside-Down Cake

Now let’s bake this beauty. Here are the steps you’ll follow:

1. Preheat Your Equipment:
   Preheat your oven to 350°F and grease a 9-inch round cake pan.
2. Combine Ingredients:
   Melt ¼ cup of butter and pour into the cake pan. Sprinkle brown sugar evenly over the butter. Arrange pineapple rings on top, placing a cherry in the center of each.
3. Prepare Your Cooking Vessel:
   Set the pan aside while you make the batter.
4. Assemble the Dish:
   In a bowl, whisk together flour, baking powder, and salt. In another bowl, cream remaining ¼ cup butter with granulated sugar until fluffy. Add eggs one at a time, then mix in vanilla. Alternately mix in dry ingredients and milk until just combined.
5. Cook to Perfection:
   Pour batter evenly over the pineapple in the pan. Bake for 40–45 minutes, or until a toothpick inserted into the center comes out clean.
6. Finishing Touches:
   Cool the cake in the pan for 10 minutes. Run a knife around the edge, then carefully invert onto a serving plate.
7. Serve and Enjoy:
   Serve warm or at room temperature. The syrupy topping and moist cake are hard to resist.

Texture & Flavor Secrets

This cake nails that combo of soft, buttery crumb and sticky, glossy topping. The pineapple becomes slightly chewy around the edges and sweetens even more as it bakes. The cherries add bright pops of color and sweetness. The cake itself is rich, but not too heavy, thanks to milk and just the right amount of eggs.

Cooking Tips & Tricks

These small tweaks make a big difference:

• Use light brown sugar for a classic sweet topping or dark for deeper flavor.
• Add a touch of cinnamon or cardamom to the batter for spice.
• For a citrusy twist, add orange zest to the cake batter.

What to Avoid

Here’s how to keep things from going sideways:

• Don’t use too much syrup from the can or the cake may turn soggy.
• Avoid overbaking—the cake should be golden and springy, not dry.
• Don’t rush the flip—let the cake rest but don’t cool completely in the pan.

Nutrition Facts

Servings: 8
Calories per serving: 340

Note: These are approximate values.

Preparation Time

Prep Time: 15 minutes
Cook Time: 45 minutes
Total Time: 1 hour

Make-Ahead and Storage Tips

This cake can be made a day ahead and stored covered at room temperature. It keeps well for up to 3 days and can be gently reheated in the microwave. For freezing, wrap individual slices and store up to 2 months. Thaw and warm before serving.

How to Serve Pineapple Upside-Down Cake

This cake is best served slightly warm, maybe with a scoop of vanilla ice cream or a dollop of whipped cream. It’s equally delightful with coffee at brunch or as a comforting evening dessert.

Creative Leftover Transformations

Don’t let a slice go to waste!

• Toast a slice and top with Greek yogurt and honey for breakfast.
• Cube and layer with whipped cream for a tropical trifle.
• Use crumbled leftovers in parfaits or as an ice cream topping.

Additional Tips

• Dry the pineapple slices with paper towels to avoid soggy topping.
• Sprinkle a pinch of sea salt over the brown sugar for contrast.
• For a boozy kick, soak the pineapple rings in rum before baking.

Make It a Showstopper

Serve on a pedestal cake stand and brush a little extra melted butter over the fruit for added shine. Garnish with mint leaves or toasted coconut for a tropical vibe.

Variations to Try

• Pineapple Coconut Cake: Add shredded coconut to the batter.
• Mini Upside-Down Cakes: Use a muffin tin for single servings.
• Apple or Pear Version: Swap the pineapple for thinly sliced apples or pears.
• Spiced Version: Add nutmeg, cinnamon, or ginger to the batter.
• Gluten-Free: Use a 1:1 gluten-free flour blend.

FAQ’s

Q1: Can I use fresh pineapple?
Yes, just slice it thinly and core the centers for the same effect.

Q2: Can I bake it in a square pan?
Absolutely. A square 8-inch pan works well—just adjust baking time slightly.

Q3: Can I make this dairy-free?
Yes, use plant-based butter and non-dairy milk.

Q4: What if my cake sticks?
Run a knife around the edges and tap the pan gently before flipping.

Q5: Can I reduce the sugar?
You can reduce granulated sugar slightly, but keep the brown sugar for the topping.

Q6: Can I freeze it whole?
Yes, wrap tightly and freeze for up to 2 months.

Q7: How do I keep the cherries from bleeding?
Pat them dry with a paper towel before placing in the pan.

Q8: Is it okay to use crushed pineapple?
It works, but the look will be less structured—great for rustic style!

Q9: Can I make cupcakes with this?
Yes! Just layer fruit in muffin tins and reduce baking time to 20–25 minutes.

Q10: Can I double the recipe?
Yes, use a 9×13 inch pan and double all ingredients.

Conclusion

Pineapple Upside-Down Cake is a timeless dessert that’s as fun to make as it is to eat. From the caramelized fruit topping to the buttery cake beneath, every bite brings a hit of sweetness and nostalgia. Whether it’s your first time flipping or your hundredth, this cake always brings a little magic to the table.

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