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Pineapple Upside-Down Cake is the ultimate retro dessert that never goes out of style. With its golden, caramelized pineapple rings, bright red cherries, and soft, buttery cake, this classic treat is as visually stunning as it is delicious. Whether you’re serving it for a family dinner, holiday gathering, or just because you’re craving something sweet, this cake is sure to delight all ages.

There’s something magical about flipping a cake out of the pan to reveal the perfectly arranged fruit topping. It feels like a little celebration every time! Plus, this recipe is surprisingly easy to make, even for beginners. With a cast iron skillet and a few simple steps, you can whip up a dessert that looks straight out of a bakery.

Let’s dive into the process of creating this show-stopping dessert. By the end, you’ll have a new favorite to add to your repertoire!

Recipe Overview

Pineapple Upside-Down Cake is a classic dessert that combines the sweetness of caramelized fruit with the lightness of a tender cake. What sets it apart is its signature presentation. The pineapples and cherries are arranged in a beautiful pattern at the bottom of the pan, and when the cake is flipped after baking, they become the star of the show.

The base of the cake is delightfully simple, often made with a boxed cake mix for convenience. You’ll enhance the mix with pineapple juice for extra flavor, resulting in a moist and fluffy texture. The topping, made with melted butter, brown sugar, and the fruit, caramelizes in the oven to create a sticky-sweet layer that pairs perfectly with the soft cake.

This dessert is perfect for any occasion. It’s nostalgic yet timeless, and it’s easy to customize to suit your taste.

Key Ingredients

For the Topping:

  • Butter: Creates the base for the caramelized topping, giving it a rich, buttery flavor.
  • Brown Sugar: Adds sweetness and helps form the gooey caramel glaze.
  • Pineapple Rings: The centerpiece of this cake, their tangy sweetness balances the richness of the caramel.
  • Maraschino Cherries: Bright pops of color and sweetness that complete the retro look.

For the Cake:

  • Cake Mix: A boxed mix makes this recipe quick and easy, but you can also use your favorite homemade vanilla or yellow cake recipe.
  • Pineapple Juice: Enhances the cake’s flavor, tying it to the topping.
  • Vegetable Oil and Eggs: Essential for creating a moist and fluffy cake.

How to Make Pineapple Upside-Down Cake

Step 1: Prepare Your Ingredients and Skillet

Preheat your oven to the temperature specified on your cake mix box, usually around 350°F. Drain the canned pineapple, reserving the juice for the cake batter. Arrange the pineapple rings and cherries on a plate, ready for assembly.

In a cast iron skillet, melt the butter over medium heat. Once melted, sprinkle the brown sugar evenly over the butter, creating the base for the caramel topping. Remove the skillet from the heat and let it cool slightly.

Step 2: Assemble the Topping

Arrange the pineapple rings in the skillet on top of the brown sugar and butter mixture. Place one cherry in the center of each ring. If you have extra pineapple, you can cut it into pieces and fill in any gaps between the rings.

Step 3: Prepare the Cake Batter

In a large mixing bowl, prepare the cake batter according to the instructions on the box. Replace the water in the recipe with an equal amount of the reserved pineapple juice for extra flavor. Mix in the vegetable oil and eggs until smooth.

Step 4: Combine and Bake

Pour the prepared cake batter over the arranged fruit in the skillet, spreading it evenly to cover the fruit completely. Be gentle to avoid disturbing the pattern.

Place the skillet in the preheated oven and bake until a toothpick inserted in the center comes out clean. This typically takes about 25-30 minutes, depending on your oven.

Step 5: Cool and Flip

Once the cake is done, remove it from the oven and let it cool in the skillet for about 10 minutes. Don’t wait too long—flipping the cake while it’s still warm ensures the topping releases easily.

Run an offset spatula around the edges of the cake to loosen it. Place a large plate or platter over the skillet, then quickly but carefully flip the skillet and plate together. Lift the skillet away to reveal your beautifully caramelized pineapple topping.

Tips for Success

  1. Use Pineapple Juice: Swap the water in your cake batter for pineapple juice to tie the flavors together and create a moist texture.
  2. Don’t Let It Cool Completely: Flip the cake while it’s still warm to prevent the caramel topping from sticking to the pan.
  3. Be Precise with the Topping: Arrange the fruit carefully, as it will be the focal point of your cake once flipped.
  4. Use a Cast Iron Skillet: A cast iron skillet evenly distributes heat and gives the cake a gorgeous caramelization.
  5. Check for Doneness: Insert a toothpick into the center of the cake. If it comes out clean, your cake is ready.

Variations and Customizations

  • Lemon Twist: Use lemon cake mix instead of white or yellow for a bright, citrusy flavor.
  • Coconut Flair: Sprinkle shredded coconut between the pineapple rings for a tropical twist.
  • Fresh Fruit: Swap the canned pineapple and cherries for fresh pineapple slices and pitted cherries for a fresher taste.
  • Upscale Version: Add a splash of almond extract to the cake batter for a subtle, nutty undertone.
  • Mini Cakes: Use muffin tins to create individual pineapple upside-down cakes—perfect for parties!

Serving and Storage Tips

Serving Suggestions

This cake is best enjoyed warm, when the caramel topping is still gooey and the cake is soft. Add a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent touch.

Storage Instructions

  • Room Temperature: Keep the cake covered at room temperature for up to two days.
  • Refrigeration: Store it in the fridge for up to four days in an airtight container.
  • Freezing: Wrap the cooled cake in plastic wrap and aluminum foil, then freeze for up to three months. Thaw in the fridge before serving.

Closing

Pineapple Upside-Down Cake is a timeless dessert that combines stunning presentation with irresistible flavor. Its caramelized topping, moist cake, and nostalgic charm make it a hit at any table.

So, why not bring a slice of retro magic to your next gathering? This recipe is easy enough for beginners and impressive enough to wow your guests. Once you’ve tried it, you’ll understand why this classic cake has stood the test of time. Happy baking!

Print
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Pineapple Upside-Down Cake


  • Author: Sarah
  • Total Time: 60 minutes
  • Yield: 12 servings 1x

Description

This timeless pineapple upside-down cake features sweet caramelized pineapple and cherries baked in a soft and fluffy cake. Made in a cast iron skillet, it’s a beautiful and easy dessert that will impress your guests and quickly become a favorite.


Ingredients

Scale
  • 1 (20 ounce) can pineapple rings
  • 1/4 cup water, or as needed
  • 1/2 cup unsalted butter
  • 1 (15.25 ounce) package white cake mix
  • 1/2 cup vegetable oil
  • 3 large egg whites
  • 1 1/2 cups brown sugar
  • 7 maraschino cherries

Instructions

  1. Preheat your oven to 350°F (175°C).
  2. Drain the canned pineapple and measure the juice. Add water if needed to make 1 cup of liquid. Set aside 7 pineapple rings and the juice for the recipe.
  3. Melt the butter in a 10- or 11-inch cast iron skillet over medium-high heat.
  4. Sprinkle the brown sugar evenly over the melted butter. Arrange 6 pineapple rings around the edge of the skillet and 1 in the center. Place a maraschino cherry in the center of each ring.
  5. In a large mixing bowl, combine the cake mix, reserved pineapple juice, vegetable oil, and egg whites. Beat the mixture with an electric mixer on medium speed for 2 minutes, until smooth.
  6. Carefully pour the prepared batter over the arranged pineapple and cherries in the skillet, spreading it evenly.
  7. Bake the cake in the preheated oven for 25–28 minutes, or until a toothpick inserted in the center comes out clean.
  8. Let the cake cool in the skillet for 10 minutes, but not longer to prevent sticking. Run a spatula around the edges to loosen the cake.
  9. Place a serving plate over the skillet. Carefully flip the skillet to release the cake onto the plate. If any pineapple or caramel sticks to the skillet, gently transfer it back onto the cake.

Notes

Use pineapple juice instead of water in the cake mix for extra flavor. Store the cake at room temperature for 1–2 days or refrigerate for up to 4 days. It can also be frozen for up to 3 months.

  • Prep Time: 20 minutes
  • Cook Time: 30 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 slice
  • Calories: 399
  • Sugar: 40g
  • Sodium: 350mg
  • Fat: 18g
  • Saturated Fat: 9g
  • Unsaturated Fat: 9g
  • Trans Fat: 0g
  • Carbohydrates: 59g
  • Fiber: 1g
  • Protein: 3g
  • Cholesterol: 45mg

Keywords: pineapple, dessert, cake, retro

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