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Introduction & Inspiration: A Tropical Classic, Reimagined

This Pineapple Upside-Down Cake is a sunny, sweet, and utterly delicious dessert! I love the combination of the tender, buttery cake, the caramelized pineapple topping, and the bright, cheerful presentation. It’s a classic for a reason.

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The inspiration for this recipe comes from the classic Pineapple Upside-Down Cake. But with a few key tweaks to enhance the flavor and texture. I wanted a cake that was both moist and flavorful.

I’ve experimented with different variations of this cake over the years. And this recipe is the culmination of that experimentation. It’s a recipe that I’m incredibly proud of.

This cake is perfect for any occasion, from a casual weeknight dessert to a special celebration. It’s a guaranteed crowd-pleaser. And it’s a beautiful centerpiece for any dessert table.

Nostalgic Appeal (and the Charm of Upside-Down Cakes)

Pineapple Upside-Down Cake is a dessert that evokes a sense of nostalgia and retro charm for many. It reminds me of vintage cookbooks, family gatherings, and the simple pleasure of a classic, home-baked cake. It’s timeless.

This recipe captures that classic appeal. With its caramelized pineapple topping and its moist, tender cake. It’s a way to enjoy a beloved dessert.

There’s something inherently fun and visually appealing about an upside-down cake. The reveal of the beautifully arranged fruit topping when you invert the cake is always a moment of delight. It is dramatic.

It’s the kind of cake that’s perfect for sharing with loved ones. Or for enjoying all to yourself with a cup of coffee or tea. It’s a celebration of simple ingredients and classic baking techniques.

Homemade Focus (and the Superiority of Scratch Baking)

I’m a strong advocate for homemade baked goods, and this Pineapple Upside-Down Cake is a perfect example of why. Making your own cake allows you to control the ingredients, the flavors, and the quality of the final product. It is worth it.

Store-bought versions of similar cakes often lack the fresh flavor, the moist texture, and the perfect balance of sweetness and tartness that you can achieve with homemade. When you bake from scratch, you can use the best ingredients.

This recipe is a testament to the fact that even seemingly complex desserts like upside-down cakes can be made at home with relative ease. It requires a bit of time and attention to detail. But the steps are straightforward.

It’s a recipe that I encourage everyone to try. It’s a great way to experience the true flavors of Pineapple Upside-Down Cake. And to enjoy the satisfaction of creating something beautiful.

Flavor Goal

The flavor goal of this Pineapple Upside-Down Cake is to achieve a perfect balance of sweet and tart. With a moist, tender cake, a rich, buttery caramel topping, and the bright, tropical flavor of pineapple.

The cake itself, made with butter, sugar, vanilla extract, eggs, flour, baking powder, baking soda, salt, and sour cream. It is tender, moist, and subtly sweet. It provides the perfect base.

The caramel topping, made with butter, brown sugar, honey, salt, and orange juice. Creates a rich, buttery, and slightly tangy layer that complements the pineapple beautifully.

The pineapple slices, arranged in the bottom of the pan before the batter is added. Become caramelized and intensely flavorful during baking. The maraschino cherries add a pop of color.

Ingredient Insights

Let’s take a closer look at the ingredients that make this Pineapple Upside-Down Cake so special.

Baking spray with flour (or butter and flour) is used to grease the cake pan and prevent sticking.

A 15-ounce can and an 8-ounce can of pineapple slices in juice, drained and patted dry. Using canned pineapple is a convenient shortcut.

Granulated sugar, divided, is used to sweeten both the caramel topping and the cake batter. Cornstarch is used to thicken.

Maraschino cherries add a pop of color. Unsalted butter, softened and divided, is used in both the caramel topping and the cake batter.

Light brown sugar adds a rich, molasses-like flavor to the caramel topping. Honey adds sweetness and helps to create a smooth, glossy caramel.

Kosher salt, divided, enhances the flavors of the other ingredients and balances the sweetness. Orange juice adds a touch of citrusy brightness to the caramel topping.

Vanilla extract complements the other flavors in the cake batter. Large eggs, at room temperature.

All-purpose flour, baking powder, baking soda are key. Sour cream, at room temperature.

Essential Equipment

You’ll need a few key pieces of equipment:

A 9×13-inch baking pan.

Parchment paper.

Medium and large bowls: For mixing.

A whisk.

A medium stainless-steel skillet: for the caramel.

A stand mixer (or a hand mixer) for making the cake batter.

A rubber spatula.

That’s it! This recipe is relatively straightforward in terms of equipment.

List of Ingredients with Measurements

Here’s the complete list of ingredients, with precise measurements:

Baking spray with flour
1 15-ounce can pineapple slices in juice
1 8-ounce can pineapple slices in juice
2 cups plus 2 tablespoons granulated sugar, divided
1 Tbsp. cornstarch
12 maraschino cherries
1 ¾ cups unsalted butter, softened and divided
¾ cup packed light brown sugar
1 ½ tsp. kosher salt, divided
1 Tbsp. orange juice
1 tsp. vanilla extract
3 large eggs, room temperature
3 cups all-purpose flour
2 tsp. baking powder
1 tsp. baking soda
1 cup sour cream, room temperature
Ice cream, to serve
Whipped cream, to serve

These are the quantities from the original recipe.

Remember to use fresh, high-quality ingredients whenever possible.

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Step-by-Step Instructions

Ready to bake a stunning Pineapple Upside-Down Cake? Here’s a detailed, step-by-step guide:

1. Prepare the Pan and Oven:

Preheat the oven to 350°F (175°C).

Spray a 9×13-inch baking pan with baking spray with flour.

Line the bottom of the pan with parchment paper. Do not spray the parchment paper again.

2. Prepare the Pineapple: Drain the pineapple slices (both cans) and reserve the juice for later use.

Pat the pineapple slices dry with paper towels. This is important to prevent the cake from becoming soggy.

Place the pineapple slices in a large bowl.

Sprinkle the pineapple slices with 2 tablespoons of granulated sugar and the cornstarch. Toss gently to coat.

Arrange the pineapple slices in the prepared pan, fitting them snugly together.

Add the maraschino cherries to the centers of the pineapple rings.

3. Make the Caramel:

In a medium stainless-steel skillet, melt ¾ cup of the softened butter over medium heat.

Stir in the light brown sugar and ½ teaspoon of the kosher salt.

Bring the mixture to a simmer. Cook until the sugar is melted and fragrant, about 3 minutes.

Slowly pour in 3 tablespoons of the reserved pineapple juice, whisking until combined and smooth.

Pour the caramel evenly over the pineapple slices in the pan.

4. Make the Cake Batter: In the bowl of a stand mixer (or using a hand mixer and a large bowl), beat the remaining 1 cup of softened butter, the remaining 2 cups of granulated sugar, the orange zest (if using), and the vanilla extract at medium speed until creamy, 2 to 3 minutes. Stopping occasionally to scrape the sides of the bowl.

Add the eggs, one at a time, beating well after each addition.

In a medium bowl, whisk together the all-purpose flour, baking powder, baking soda, and the remaining 1 teaspoon of kosher salt.

Gradually add the flour mixture to the butter mixture alternately with the sour cream. Beginning and ending with the flour mixture. Beat just until combined after each addition. Be careful not to overmix.

5. Pour Batter over Pineapple and Caramel: Carefully dollop the batter onto the pineapple and caramel in the pan.

Gently spread the batter with an offset spatula or the back of a spoon, making sure not to press too hard or move the pineapple slices.

6. Bake:

Bake for 30 minutes.

Place a piece of foil on top of the cake to prevent excess browning.

Continue baking until a wooden pick inserted into the center of the cake comes out clean, 15 to 20 minutes more.

7. Cool and Invert:

Remove the foil.

Let the cake cool in the pan on a wire rack for 10 minutes.

Run a thin knife or offset spatula around the sides of the cake to loosen it from the pan.

Carefully invert the cake onto a serving plate.

Remove the parchment paper.

Let the cake cool completely.

8. Serve: Serve warm, at room temperature, or cold.

Serve with ice cream or whipped cream, if desired. Enjoy!

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Troubleshooting

Here are some potential problems, and solutions:

Problem: The cake is dry.

Solution: Make sure you’re not overbaking the cake. Also, be sure to measure the flour correctly (spoon and level method, or use a kitchen scale).

Problem: The cake is dense.

Solution: Make sure you’re not overmixing the batter. Also, make sure your baking powder and baking soda are fresh.

Problem: The caramel is too runny.

Solution: Make sure you’re cooking the caramel until the sugar is completely melted and the mixture is slightly thickened.

Problem: The cake is sticking to the pan.

Solution: Make sure you’re greasing the pan thoroughly and lining the bottom with parchment paper. Also, make sure to run a knife around the edges of the cake before inverting it.

Problem: Cake is sinking in the middle. Solution: Make sure oven temperature is correct.

Tips and Variations

Here are some helpful tips:

Tip: For an even richer flavor, use brown butter in the cake batter.

Tip: If you don’t have parchment paper, you can grease and flour the pan thoroughly.

Tip: To make sure your cake is evenly baked, rotate the pan halfway through the baking time.

Variation: Add a teaspoon of ground cinnamon or nutmeg to the cake batter for extra spice.

Variation: Use fresh pineapple instead of canned pineapple. Cut the pineapple into rings or chunks.

Variation: Add a layer of chopped nuts, such as pecans or macadamia nuts, to the caramel topping before adding the cake batter.

Variation: Drizzle the finished cake with a glaze made from powdered sugar and pineapple juice.

Variation: Add coconut flakes to the batter.

Serving and Pairing Suggestions

This dessert is perfect for many occasions:

Serving Suggestions:

Serve the cake warm, at room temperature, or cold.

Serve it with a scoop of vanilla ice cream, whipped cream, or a dollop of crème fraîche.

Serve it as a dessert for a summer barbecue, a potluck, a picnic, or any casual gathering.

It’s also perfect for a special occasion, such as a birthday or holiday celebration.

Pairing Suggestions:

This cake pairs well with a variety of beverages.

A cup of coffee or tea.

A glass of milk.

A dessert wine, such as a Moscato d’Asti or a late-harvest Riesling.

A tropical cocktail, such as a Piña Colada or a Mai Tai.

It is a wonderful dessert.

Nutritional Information

Here’s an approximate nutritional breakdown per serving (assuming 12 servings):

Calories: Approximately 400-500
Protein: 4-6 grams
Fat: 20-30 grams (mostly from the butter and oil)
Carbohydrates: 50-60 grams
Fiber: 1-2 grams

This is a general estimate. This Pineapple Upside-Down Cake is a relatively rich and decadent dessert. Due to the butter, sugar, and caramel topping.

It does provide some vitamins and minerals from the pineapple. It’s best enjoyed in moderation as part of a balanced diet.

You can reduce the fat and calories by using less butter and sugar.

Pineapple Upside-Down Cake

Author: Alyssa

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Description

Ingredients

Scale

Baking spray with flour
1 15-ounce can pineapple slices in juice
1 8-ounce can pineapple slices in juice
2 cups plus 2 tablespoons granulated sugar, divided
1 Tbsp. cornstarch
12 maraschino cherries
1 ¾ cups unsalted butter, softened and divided
¾ cup packed light brown sugar
1 ½ tsp. kosher salt, divided
1 Tbsp. orange juice
1 tsp. vanilla extract
3 large eggs, room temperature
3 cups all-purpose flour
2 tsp. baking powder
1 tsp. baking soda
1 cup sour cream, room temperature
Ice cream, to serve
Whipped cream, to serve

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