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Old Fashioned Pineapple Upside-Down Cake

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Introduction: Can a Cake Take You Back in Time?

Ever wondered what dessert your grandma might’ve served at a Sunday family gathering? Old Fashioned Pineapple Upside-Down Cake is that nostalgic treat, with its golden pineapple rings, sweet caramelized topping, and tender, almond-scented cake. This retro classic is as beautiful as it is delicious, with vibrant pineapple and cherries flipped upside down for a stunning presentation. Ready to bake a cake that’s a slice of vintage charm? Let’s get started and bring this timeless dessert to life!

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Overview: Why Old Fashioned Pineapple Upside-Down Cake is a Classic

Old Fashioned Pineapple Upside-Down Cake is a beloved dessert that combines a buttery, caramelized pineapple topping with a light, fluffy cake. Baked in a single skillet and flipped to reveal its gorgeous fruit topping, it’s a showstopper that’s surprisingly easy to make. Here’s what makes it special:

  • Time Requirement: About 20 minutes to prep, 30-35 minutes to bake, plus a few minutes for cooling.
  • Difficulty Level: Moderate—easy mixing, but requires careful egg whipping and flipping technique.
  • Why It’s Special: The combination of sweet, caramelized pineapple, tart cherries, and a tender cake infused with almond flavor creates a perfect balance. Its retro vibe and stunning presentation make it ideal for gatherings, and it’s versatile enough to pair with whipped cream or ice cream.

Perfect for holidays, potlucks, or a cozy family dessert, this cake brings warmth and nostalgia to any table.

Essential Ingredients

Old Fashioned Pineapple Upside-Down Cake uses simple ingredients to create its iconic look and taste. Here’s what you’ll need for 12 servings:

  • ½ cup butter: Melts into a caramel-like base for the topping.
  • 1 cup packed light brown sugar: Creates a sweet, gooey topping that caramelizes with the fruit.
  • 1 (20-ounce) can sliced pineapple: The star of the topping, adding juicy sweetness.
  • 10 maraschino cherries, halved: Adds a pop of color and tart flavor.
  • 1 cup sifted cake flour: Ensures a light, tender cake.
  • 1 teaspoon baking powder: Helps the cake rise and stay fluffy.
  • ¼ teaspoon salt: Balances the sweetness.
  • 4 large eggs: Whipped separately for a light, airy texture.
  • 1 cup white sugar: Sweetens the cake batter.
  • 1 tablespoon butter, melted: Adds richness to the batter.
  • 1 teaspoon almond extract: Infuses the cake with a warm, nutty flavor.

Why These Ingredients Matter

  • Pineapple and Cherries: The fruit topping creates a vibrant, caramelized layer that’s both beautiful and flavorful.
  • Brown Sugar and Butter: These form a gooey, caramel-like base that soaks into the fruit during baking.
  • Cake Flour: Its low protein content ensures a soft, tender cake that contrasts the sticky topping.
  • Egg Whites: Whipped to peaks, they give the cake its signature light, fluffy texture.

Substitutions and Variations

  • Pineapple: Use fresh pineapple slices (about 8-10 slices) or canned pineapple chunks for a different look.
  • Cherries: Swap maraschino cherries for fresh pitted cherries or omit for a simpler topping.
  • Flour: Substitute cake flour with ¾ cup all-purpose flour mixed with 2 tablespoons cornstarch.
  • Extract: Use vanilla extract instead of almond for a classic flavor, or try coconut extract for a tropical twist.
  • Gluten-Free: Use a gluten-free cake flour blend to make it gluten-free.
  • Vegan Option: Replace butter with vegan butter, eggs with a vegan egg substitute (like aquafaba), and ensure cherries are vegan-friendly.
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Step-by-Step Instructions

Making Old Fashioned Pineapple Upside-Down Cake is fun and straightforward, with a few key techniques to ensure success. Let’s bake!

Step 1: Preheat and Prep the Pan

  • Preheat your oven to 325°F (165°C).
  • In a 10-inch heavy skillet with a heat-resistant handle (or cast iron pan), melt ½ cup butter over very low heat.
  • Remove from heat and sprinkle 1 cup packed light brown sugar evenly over the melted butter.
  • Arrange pineapple slices to cover the bottom of the skillet, placing halved maraschino cherries in the centers and gaps of the pineapple slices.

Tip: Arrange the pineapple slices in a decorative pattern, as this will be the top of the cake when flipped.

Step 2: Prepare the Dry Ingredients

  • In a medium bowl, sift together 1 cup cake flour, 1 teaspoon baking powder, and ¼ teaspoon salt. Set aside.

Tip: Sifting aerates the flour for a lighter cake texture.

Step 3: Whip the Egg Whites

  • Separate 4 large eggs, placing the whites in a large mixing bowl and the yolks in a smaller bowl.
  • Beat the egg whites with an electric mixer on medium speed until soft peaks form.
  • Gradually add 1 cup white sugar, beating well after each addition, until medium-stiff peaks form.

Tip: Medium-stiff peaks hold their shape but curl slightly at the tips. Don’t overbeat, or the whites can become dry.

Step 4: Mix the Batter

  • Beat the egg yolks on high speed until thick and pale yellow, about 2-3 minutes.
  • Using a wire whisk or rubber spatula, gently fold the yolks into the whipped egg whites with an over-and-under motion.
  • Gradually fold in the sifted flour mixture until just blended.
  • Fold in 1 tablespoon melted butter and 1 teaspoon almond extract.

Tip: Fold gently to keep the batter airy—avoid stirring, which can deflate the egg whites.

Step 5: Bake the Cake

  • Spread the batter evenly over the pineapple and cherry layer in the skillet.
  • Bake for 30-35 minutes, or until a toothpick inserted in the center comes out clean.

Tip: Check at 30 minutes, as ovens vary, to avoid overbaking.

Step 6: Cool and Flip

  • Remove the cake from the oven and let it cool in the skillet for 5 minutes.
  • Run a table knife around the edges to loosen the cake.
  • Place a serving plate over the skillet and carefully invert to flip the cake onto the plate, revealing the pineapple topping.

Tip: Flip confidently but carefully to keep the topping intact. If any pineapple sticks to the pan, gently place it back on the cake.

Step 7: Serve

  • Slice into wedges and serve warm or at room temperature.

Tip: Use a serrated knife for clean cuts through the fruit topping.

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Assembly: Building the Perfect Pineapple Upside-Down Cake

Assembling Old Fashioned Pineapple Upside-Down Cake is all about creating a stunning, fruit-topped dessert. Here’s how to make it shine:

  • Topping Base: Arrange the pineapple slices and cherries in a pretty pattern over the brown sugar and butter for a vibrant, caramelized top.
  • Batter: Spread the airy batter gently over the fruit to avoid disturbing the design.
  • Flipping: Invert the cake carefully to reveal the glossy, fruit-studded topping.
  • Presentation: Serve on a large, round platter to show off the golden pineapple and bright cherries.

Presentation Tips

  • Place a cherry half in the center of each pineapple ring for a classic look.
  • Serve with a dollop of whipped cream or a scoop of vanilla ice cream for extra indulgence.
  • Dust with powdered sugar or drizzle with a little caramel sauce for a fancy touch.

Storage and Make-Ahead Tips

This cake is best fresh but can be stored or prepped ahead for convenience.

  • Storage:
    • Store covered at room temperature for up to 1 day or in the fridge for up to 3 days.
    • Freeze the baked cake (wrapped tightly in plastic wrap and foil) for up to 2 months. Thaw in the fridge overnight before serving.
  • Make-Ahead:
    • Prepare the pineapple and cherry topping in the skillet a day ahead and store covered in the fridge.
    • Make the dry ingredient mix (flour, baking powder, salt) a day in advance and store in an airtight container.
    • Bake the cake a day ahead for best flavor, as the topping melds with the cake over time.

Tip: Reheat slices in a 300°F oven for 5-10 minutes to revive the caramelized topping’s texture.

Recipe Variations

Old Fashioned Pineapple Upside-Down Cake is a great base for creative twists. Here are some ideas:

  • Tropical Upside-Down Cake: Add ½ cup shredded coconut to the topping or batter for a tropical flair.
  • Peach Upside-Down Cake: Swap pineapple for canned or fresh peach slices.
  • Rum-Infused Cake: Replace almond extract with 1 tablespoon rum for a Caribbean vibe.
  • Gluten-Free: Use a gluten-free cake flour blend for a gluten-free version.
  • Mini Cakes: Divide the topping and batter into muffin tins for individual upside-down cakes (bake for 15-20 minutes).

Conclusion: Savor the Retro Sweetness!

Old Fashioned Pineapple Upside-Down Cake is a dessert that brings nostalgia and joy to every bite. Its caramelized pineapple, tart cherries, and fluffy almond-scented cake make it a timeless treat that’s perfect for any occasion, from family dinners to festive celebrations. With simple ingredients and a few easy techniques, you can create a stunning dessert that looks as good as it tastes. So, grab your skillet, channel some vintage vibes, and bake this classic. We’d love to see your creations—share them in the comments or on social media!

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Old Fashioned Pineapple Upside-Down Cake

  • Author: Alyssa

Description

Ever wondered what dessert your grandma might’ve served at a Sunday family gathering? Old Fashioned Pineapple Upside-Down Cake is that nostalgic treat, with its golden pineapple rings, sweet caramelized topping, and tender, almond-scented cake.


Ingredients

Scale

Old Fashioned Pineapple Upside-Down Cake uses simple ingredients to create its iconic look and taste. Here’s what you’ll need for 12 servings:

  • ½ cup butter: Melts into a caramel-like base for the topping.
  • 1 cup packed light brown sugar: Creates a sweet, gooey topping that caramelizes with the fruit.
  • 1 (20-ounce) can sliced pineapple: The star of the topping, adding juicy sweetness.
  • 10 maraschino cherries, halved: Adds a pop of color and tart flavor.
  • 1 cup sifted cake flour: Ensures a light, tender cake.
  • 1 teaspoon baking powder: Helps the cake rise and stay fluffy.
  • ¼ teaspoon salt: Balances the sweetness.
  • 4 large eggs: Whipped separately for a light, airy texture.
  • 1 cup white sugar: Sweetens the cake batter.
  • 1 tablespoon butter, melted: Adds richness to the batter.
  • 1 teaspoon almond extract: Infuses the cake with a warm, nutty flavor.

Why These Ingredients Matter

  • Pineapple and Cherries: The fruit topping creates a vibrant, caramelized layer that’s both beautiful and flavorful.
  • Brown Sugar and Butter: These form a gooey, caramel-like base that soaks into the fruit during baking.
  • Cake Flour: Its low protein content ensures a soft, tender cake that contrasts the sticky topping.
  • Egg Whites: Whipped to peaks, they give the cake its signature light, fluffy texture.

Substitutions and Variations

  • Pineapple: Use fresh pineapple slices (about 8-10 slices) or canned pineapple chunks for a different look.
  • Cherries: Swap maraschino cherries for fresh pitted cherries or omit for a simpler topping.
  • Flour: Substitute cake flour with ¾ cup all-purpose flour mixed with 2 tablespoons cornstarch.
  • Extract: Use vanilla extract instead of almond for a classic flavor, or try coconut extract for a tropical twist.
  • Gluten-Free: Use a gluten-free cake flour blend to make it gluten-free.
  • Vegan Option: Replace butter with vegan butter, eggs with a vegan egg substitute (like aquafaba), and ensure cherries are vegan-friendly.


Instructions

Step 1: Preheat and Prep the Pan

  • Preheat your oven to 325°F (165°C).
  • In a 10-inch heavy skillet with a heat-resistant handle (or cast iron pan), melt ½ cup butter over very low heat.
  • Remove from heat and sprinkle 1 cup packed light brown sugar evenly over the melted butter.
  • Arrange pineapple slices to cover the bottom of the skillet, placing halved maraschino cherries in the centers and gaps of the pineapple slices.

Tip: Arrange the pineapple slices in a decorative pattern, as this will be the top of the cake when flipped.

Step 2: Prepare the Dry Ingredients

  • In a medium bowl, sift together 1 cup cake flour, 1 teaspoon baking powder, and ¼ teaspoon salt. Set aside.

Tip: Sifting aerates the flour for a lighter cake texture.

Step 3: Whip the Egg Whites

  • Separate 4 large eggs, placing the whites in a large mixing bowl and the yolks in a smaller bowl.
  • Beat the egg whites with an electric mixer on medium speed until soft peaks form.
  • Gradually add 1 cup white sugar, beating well after each addition, until medium-stiff peaks form.

Tip: Medium-stiff peaks hold their shape but curl slightly at the tips. Don’t overbeat, or the whites can become dry.

Step 4: Mix the Batter

  • Beat the egg yolks on high speed until thick and pale yellow, about 2-3 minutes.
  • Using a wire whisk or rubber spatula, gently fold the yolks into the whipped egg whites with an over-and-under motion.
  • Gradually fold in the sifted flour mixture until just blended.
  • Fold in 1 tablespoon melted butter and 1 teaspoon almond extract.

Tip: Fold gently to keep the batter airy—avoid stirring, which can deflate the egg whites.

Step 5: Bake the Cake

  • Spread the batter evenly over the pineapple and cherry layer in the skillet.
  • Bake for 30-35 minutes, or until a toothpick inserted in the center comes out clean.

Tip: Check at 30 minutes, as ovens vary, to avoid overbaking.

Step 6: Cool and Flip

  • Remove the cake from the oven and let it cool in the skillet for 5 minutes.
  • Run a table knife around the edges to loosen the cake.
  • Place a serving plate over the skillet and carefully invert to flip the cake onto the plate, revealing the pineapple topping.

Tip: Flip confidently but carefully to keep the topping intact. If any pineapple sticks to the pan, gently place it back on the cake.

Step 7: Serve

  • Slice into wedges and serve warm or at room temperature.

 

Tip: Use a serrated knife for clean cuts through the fruit topping


FAQs

1. Why did my cake stick to the skillet?

Sticking can happen if the skillet isn’t greased enough or if the cake cools too long before flipping. Ensure the butter layer is even, and invert after 5 minutes of cooling.

2. Can I use fresh pineapple instead of canned?

Yes! Use 8-10 thin slices of fresh pineapple, peeled and cored. You may need to add a tablespoon of extra brown sugar for sweetness.

3. Is this cake gluten-free?

Not as written, but you can use a gluten-free cake flour blend to make it gluten-free.

4. Why is my cake dense?

A dense cake can result from overmixing the batter or underwhipping the egg whites. Fold gently and whip egg whites to medium-stiff peaks.

5. Can I make this ahead for a party?

Yes! Bake the cake a day ahead and store covered at room temperature or in the fridge. The flavors improve as the topping soaks in.

6. Can I skip the cherries?

Absolutely! Omit the cherries or replace with other fruits like berries or small peach pieces for a different look.

7. What are the health benefits of this cake?

Pineapple provides vitamin C and fiber, and eggs offer protein. Enjoy in moderation, as the butter and sugar make this an indulgent treat.

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