Caramelized Pineapple Upside-Down Cake

After a long week, there’s truly nothing that brings more joy to our household than the aroma of something sweet baking in the oven. Last Sunday, that heavenly scent was none other than caramelized pineapple upside-down cake. From the moment the brown sugar and butter started to bubble in the skillet, filling the kitchen with a rich, toffee-like fragrance, I knew we were in for a treat. And boy, was I right! The cake emerged from the oven golden brown and beautifully moist, with that glistening, caramelized pineapple topping that’s just irresistible. Even my pickiest eater, my son, who usually shies away from fruit in desserts, devoured a slice and asked for seconds! The combination of the tangy pineapple, the rich caramel, and the fluffy, buttery cake was simply divine. It’s become an instant family favorite, and I’m so excited to share this recipe with you so you can bring a little sunshine into your kitchen too.

Ingredients

• For the Caramel Topping:
  • Unsalted Butter: 1/2 cup (1 stick), this forms the base of the caramel and adds richness.
  • Packed Light Brown Sugar: 3/4 cup, provides the deep caramel flavor and sweetness.
  • Fresh Pineapple Rings: 1 (20-ounce) can rings, or fresh pineapple sliced into rings about 1/2 inch thick, the star of the show, offering tangy sweetness and a beautiful caramelized texture. Maraschino cherries (optional): For a pop of color and classic touch, these are optional but add a festive look.
• For the Cake Batter:
  • All-Purpose Flour: 1 1/2 cups, the foundation of the cake, providing structure.
  • Granulated Sugar: 3/4 cup, adds sweetness to the cake and balances the brown sugar in the caramel.
  • Baking Powder: 1 1/2 teaspoons, a leavening agent that helps the cake rise and become fluffy.
  • Salt: 1/4 teaspoon, enhances the flavors of all the other ingredients and balances the sweetness.
  • Unsalted Butter, softened: 1/2 cup (1 stick), adds moisture, richness, and tenderness to the cake.
  • Eggs: 2 large, bind the ingredients together, add richness, and contribute to the cake’s structure.
  • Milk: 1/2 cup, adds moisture and helps to create a tender crumb.
  • Vanilla Extract: 1 teaspoon, enhances the overall flavor of the cake, adding warmth and depth.

Instructions

1. Prepare the Caramel and Pineapple Base: Preheat your oven to 350°F (175°C). In a 9-inch round oven-safe skillet (cast iron works beautifully, or any heavy-bottomed skillet that can go from stovetop to oven), melt the butter over medium heat. Once melted, sprinkle the brown sugar evenly over the butter. Cook over medium heat, stirring occasionally, until the brown sugar is melted and bubbly, about 2-3 minutes. Be careful not to burn the caramel; it should be bubbling gently. Remove the skillet from the heat.
2. Arrange the Pineapple: Arrange the pineapple rings in a single layer over the caramel in the skillet. You can cut the rings in half or use whole rings depending on the size of your skillet and preference. If using maraschino cherries, place one in the center of each pineapple ring and/or between the rings for added visual appeal and a touch of sweetness. Gently press the pineapple rings into the caramel to ensure they are slightly submerged.
3. Make the Cake Batter: In a medium bowl, whisk together the all-purpose flour, granulated sugar, baking powder, and salt until well combined. In a separate large bowl, cream together the softened butter and granulated sugar until light and fluffy using an electric mixer or by hand with a whisk. Beat in the eggs one at a time, mixing well after each addition. Gradually add the dry ingredients to the wet ingredients, alternating with the milk, beginning and ending with the dry ingredients. Mix until just combined; be careful not to overmix. Stir in the vanilla extract. The batter should be smooth and pourable.
4. Assemble and Bake: Carefully pour the cake batter evenly over the pineapple and caramel in the skillet, spreading it gently to the edges. Use a spatula to ensure the batter is evenly distributed and covers the pineapple completely. Place the skillet in the preheated oven and bake for 30-40 minutes, or until a wooden skewer inserted into the center of the cake comes out clean. The cake should be golden brown and spring back lightly when touched.
5. Cool and Invert: Once baked, remove the skillet from the oven and let it cool in the skillet for about 10-15 minutes. This cooling time is crucial as it allows the caramel to slightly set and makes inverting easier. Place a serving plate or cake stand over the skillet, ensuring it’s larger than the skillet. Holding the plate firmly against the skillet, carefully and quickly invert the cake onto the plate. Lift the skillet slowly to allow the caramel and pineapple to release and drizzle down the sides of the cake. If any pineapple slices stick to the skillet, gently remove them with a spatula and arrange them back on top of the cake.
6. Serve and Enjoy: Serve the caramelized pineapple upside-down cake warm or at room temperature. It’s delicious on its own, but even better with a dollop of whipped cream, a scoop of vanilla ice cream, or a drizzle of extra caramel sauce. Store any leftover cake in an airtight container at room temperature for up to 3 days or in the refrigerator for up to 5 days.

Nutrition Facts

(Per Serving, based on 8 servings. Nutritional values are approximate and can vary based on specific ingredients and brands used.)

• Servings: 8
• Calories: Approximately 350-400 kcal
• Total Fat: 15-20g

Preparation Time

• Prep Time: 20 minutes
• Cook Time: 30-40 minutes
• Total Time: 50-60 minutes

How to Serve

Caramelized Pineapple Upside-Down Cake is a versatile dessert that can be enjoyed in many ways. Here are some serving suggestions to elevate your experience:

• Warm: Serve the cake slightly warm, right after it has been inverted and cooled for a bit. The warmth enhances the caramel and pineapple flavors, making it extra comforting.
• Room Temperature: It’s equally delicious at room temperature, making it a great option for gatherings or potlucks where you want to prepare it ahead of time.
• With Whipped Cream: A classic pairing! A dollop of freshly whipped cream adds a light and airy contrast to the richness of the cake. You can even add a hint of vanilla or cinnamon to your whipped cream for extra flavor.
• With Vanilla Ice Cream: The cool, creamy vanilla ice cream melts slightly over the warm cake, creating a delightful combination of temperatures and textures.
• With Caramel Sauce: For an extra decadent treat, drizzle warm caramel sauce over each slice. This intensifies the caramel flavor and adds a beautiful glossy finish.
• With Toasted Coconut: Sprinkle toasted coconut flakes over the cake for a tropical twist. The nutty flavor and crunchy texture of the coconut complement the pineapple and caramel beautifully.
• With a scoop of Greek Yogurt: For a slightly lighter option, serve with a dollop of plain or vanilla Greek yogurt. It provides a tangy contrast to the sweetness of the cake.
• Alongside Fresh Berries: Add a side of fresh berries like raspberries, strawberries, or blueberries. The tartness of the berries cuts through the sweetness of the cake and adds a burst of freshness.

Additional Tips for the Perfect Caramelized Pineapple Upside-Down Cake

1. Use a Good Quality Skillet: A heavy-bottomed, oven-safe skillet, preferably cast iron, is ideal for making this cake. It distributes heat evenly for both the caramelizing process on the stovetop and baking in the oven. If you don’t have a cast iron skillet, any oven-safe skillet that is at least 9 inches in diameter will work, but ensure it’s heavy enough to prevent hot spots and scorching.
2. Don’t Overcrowd the Pineapple: Arrange the pineapple rings in a single layer in the skillet. Overcrowding can prevent proper caramelization and may result in a soggy topping. If you have extra pineapple, you can bake a second smaller cake or save it for another use.
3. Measure Flour Correctly: When measuring flour, spoon it into your measuring cup and level it off with a straight edge. Avoid scooping the flour directly from the bag, as this can pack it down and result in using too much flour, leading to a dry cake. Properly measured flour ensures the right texture and balance in your cake batter.
4. Don’t Overmix the Batter: Overmixing the cake batter can develop the gluten in the flour too much, resulting in a tough cake. Mix the wet and dry ingredients until just combined. A few streaks of flour are okay; they will incorporate during baking. Overmixing is a common mistake that can significantly affect the texture of your cake.
5. Let it Cool Slightly Before Inverting: Allow the cake to cool in the skillet for about 10-15 minutes after baking before inverting it. This cooling period allows the caramel to set slightly, making it less likely to run off completely when you invert the cake. However, don’t let it cool for too long, or the caramel might become too firm and stick to the skillet.
6. If Caramel Sticks, Use Gentle Heat: If you find that some of the caramel or pineapple is sticking to the bottom of the skillet after inverting, you can gently reheat the bottom of the skillet on the stovetop over low heat for a minute or two. This will help to loosen the caramel and allow you to scrape off any stuck pieces and arrange them back on top of the cake. Be careful not to overheat it and burn the caramel.

Frequently Asked Questions (FAQ) about Caramelized Pineapple Upside-Down Cake

Q1: Can I use canned pineapple instead of fresh pineapple?

A: Yes, canned pineapple rings work perfectly well and are a convenient option. Just make sure to drain them thoroughly before arranging them in the skillet. Using canned pineapple is a great time-saver and provides consistent results. You can also use tidbits or chunks if you prefer, though rings are traditional for the classic look.

Q2: Can I make this cake ahead of time?

A: Absolutely! You can bake the pineapple upside-down cake a day ahead of time. Store it at room temperature, loosely covered, after it has completely cooled. The flavors often meld together even more beautifully overnight. When ready to serve, it’s delicious cold, at room temperature, or you can warm it up slightly in the oven for a few minutes.

Q3: Can I add nuts to this recipe?

A: Yes, nuts would be a delicious addition! You can sprinkle chopped pecans or walnuts over the caramel and pineapple before pouring the cake batter. The nuts will toast slightly as the cake bakes, adding a wonderful crunch and nutty flavor that complements the caramel and pineapple. Consider toasting the nuts beforehand for even more enhanced flavor.

Q4: What if I don’t have brown sugar? Can I use granulated sugar for the caramel?

A: While brown sugar is ideal for the rich caramel flavor, you can substitute it with granulated sugar in a pinch. However, the caramel will have a slightly different flavor profile and may not be as deep or molasses-like. If using granulated sugar, you might want to add a tablespoon of molasses to mimic the flavor of brown sugar, or a touch of honey for depth.

Q5: My cake stuck to the pan when I tried to invert it. What went wrong?

A: Sticking can sometimes happen. Possible reasons include not enough butter in the caramel, not cooling the cake for long enough before inverting, or the caramel becoming too hard if cooled for too long. Next time, ensure you use the correct amount of butter and brown sugar for the caramel. Also, let the cake cool for the recommended 10-15 minutes before inverting. If it still sticks, try gently running a thin knife or spatula around the edges of the cake before inverting, and if necessary, use the gentle reheating method mentioned in the tips.

Q6: Can I make this recipe gluten-free?

A: Yes, you can easily adapt this recipe to be gluten-free. Simply substitute the all-purpose flour with a good quality gluten-free all-purpose flour blend. Ensure the blend is designed for baking and contains xanthan gum or another binder to provide structure to the cake. Gluten-free baking may require slightly adjusted baking times, so keep an eye on the cake and check for doneness with a skewer as usual.

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