This Pineapple Upside-Down Cake is insanely good. Soft and tender cake topped with juicy fresh pineapple, Amarena cherries, and brown sugar caramel sauce. Serve warm with vanilla ice cream—ahhhmazing.
When I was the pastry chef at Firefly Restaurant in San Francisco the thing that I was known for was creating “homey” desserts, and I think that’s fair and accurate. I am a sucker for classic Americana sweets. Give me a slice of apple pie or banana bread over a fancy French pastry any day.
I also am a dedicated and firm believer that the perfect dessert consists of something warm served with cold vanilla ice cream. All of this to say, that a slice of this pineapple upside down cake served warm from the oven with a scoop of vanilla ice cream is about as close to perfection as one dessert can strive to be.
What Is Pineapple Upside-Down Cake?
Upside-down cake is an all American dessert often thought of as a retro, homey dessert. This type of cake, with fruit on the bottom (which then becomes the top), has been popular since at least the 1920’s when the Dole Pineapple Company ran a contest for pineapple recipes and received 2,500 submissions for pineapple upside-down cake (that was 1 out of every 25 submissions).
If you love this pineapple version, I encourage you to try it with other fruit. Apples, pears, berries, apricots, or peaches would be good.
What Makes This The Best Pineapple Upside Down Cake?
- Let’s start with the cake. It is a simple sour cream cake that has the most tender, buttery crumb and is not too sweet.
- Salted butter adds balance and richness to the cake batter.
- Using only egg yolks creates a melt-in-your mouth cake with depth.
- We use fresh, not canned pineapple slices. Adding bright, tropical pineapple flavor, not tinny, musty, mushy canned pineapple.
- The cherries are top notch. This pineapple upside down cake recipe uses Amarena cherries not maraschino cherries. Amarenas are rich, tart, and not overly sweet with incredible texture.
Ingredients
- Fresh pinepple: No mushy canned stuff here.
- Amarena cherries: Spring for the fancy cherries, you won’t regret it. Use any leftovers in cocktails.
- Salted butter: Make sure the butter is at room temperature.
- Brown sugar: Light or dark brown sugar is fine.
- All purpose flour: Has the heft to stand up to the pineapple juices.
- Baking powder: Reacts with the sour cream for a light, tender cake.
- Kosher salt: Even with the salted butter we still need a little extra to make a nice balanced cake.
- Granulated sugar: For sweetening the cake batter.
- Large eggs: Yolks only
- Vanilla extract: Gentle kiss of vanilla rounds everything out.
- Sour cream: Adds tang and richness.
- Vanilla ice cream: For serving. Optional but not optional, if you know what I mean.
How To Make This Recipe
step one
Cut pineapple. Remove the ends of the pineapple then the skin by slicing it off in vertical slices. Cut the pineapple, moving around the core into 4 pieces then cut each piece into 1/4-inch thick slices. You will only use about 1/2 of the pineapple.
step two
Make the caramel. Melt butter over medium heat in a cast-iron skillet. Sprinkle the brown sugar over the melted butter and cook. Whisk constantly, until the mixture bubbles and the sugar is dissolved. You don’t want to cook it too long, just long enough to dissolve the sugar. Remove from the heat.
*The beauty of using a cast iron skillet to make this cake is you make the caramel right in the pan, which means there’s no need to use parchment paper or transfer the hot caramel to a cake pan.
step three
Arrange the pineapple. Place the pineapple slices over the caramel in concentric circles starting on the outside of the skillet with the rounded side of the slices pointing out. Place the cherries here and there pushing them down so they stick in the caramel. I also like to pour a little bit of the cherry syrup over the fruit for extra cherry flavor.
step four
Sift dry ingredients. Sift the flour, baking powder, and 1/2 teaspoon salt through a fine mesh sieve into a large bowl. Dump whatever salt that stays in the sieve into the bowl.
step five
Make the batter. Beat the 6 tablespoons butter and sugar in a stand mixer then add the egg yolks and 1 1/2 teaspoons vanilla extract. Add the dry ingredients in three batches alternating with the sour cream. Mix only until it is combined. The batter will be thick, that’s good. You want the cake to be dense to soak up the pineapple juice.
step six
Bake. Evenly spread the mixture over the pineapple being careful not to disturb the fruit and bake at 350°F for 40-50 minutes or until the top is golden and has a few gentle cracks in it and a toothpick inserted in the middle comes out mostly clean.
step seven
Cool and flip. Let the cake cool on a wire rack for 15 mins—not any longer—then run a knife around the edge of the skillet and invert the cake on to a large plate or serving platter. Let cool for another 30 minutes before slicing and serving warm with vanilla ice cream.
Storage Tips
The cake is best served warm from the oven but it can sit out on the counter at room temperature for up to 8 hours. Any longer than that and the cake should be wrapped tightly in plastic wrap and refrigerated for up to 5 days. Or it can be frozen for up to 3 months. The cake gets very dense when it is cold. Rewarm in the microwave or in a 350°F oven.
Pineapple Upside-Down Cake FAQ’s
Can I make this in a cake pan? Yes, you can use a round cake pan that is 9 or 10 inches wide. The wider the pan, the thinner the cake part will be. You can also use a 2-quart baking dish.
How do I make this ahead? You can assemble the cake and not bake it up to a day in advance. Wrap the skillet with plastic wrap and refrigerate. Then bake from cold. Add an extra 5-10 minutes to the bake time.
How do you get pineapple upside down cake to not stick to the pan? The secret is to not let it cool too long. The longer it sits, the more the caramel hardens and tends to stick. If the cake is sticking to the pan, warm the skillet on the stove for a couple of minutes to liquify the caramel and try again.
If You Love This Easy Pineapple Upside-Down Cake, Try…
- Homemade Conchas {Mexican Pan Dulce}
- Authentic Tres Leches Cake
- Molasses Banana Bread
- Strawberry Tres Leches Cake
- Creamy Coconut Lime Paletas
- Cajeta {Goat’s Milk Caramel}
- 12 S’mores Combinations That Will Blow Your Mind
Perfect Upside Down Pineapple Cake
Can be yours! Give this recipe a try then let me know when you make it by snapping a pic and tagging me on Instagram @holajalapeno and #holajalapeno so I can see or leave me a comment below (don’t forget to leave a ⭐️⭐️⭐️⭐️⭐️ rating)! Also, sign up for my weekly newsletter, lots of good stuff there too!
Pineapple Upside Down Cake
This Pineapple Upside-Down Cake is insanely good. Soft and tender cake topped with juicy fresh pineapple, Amarena cherries, and brown sugar caramel sauce. Serve warm with vanilla ice cream—ahhhmazing.
Ingredients
Topping
- 1/4 cup salted butter
- 1/2 cup dark brown sugar
- 1 medium pineapple, peeled, cored, sliced lengthwise, then sliced into 1/4-inch thick wedges
- 9-12 Amarena cherries, (add as many as you'd like)
Cake
- 1 1/4 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/2 teaspoons kosher salt
- 6 tablespoons salted butter, room temperature
- 3/4 cup granulated sugar
- 1 1/2 teaspoons vanilla extract
- 3 large egg yolks, room temperature
- 3/4 cup sour cream
For Serving
- Vanilla ice cream, optional
Instructions
To Make The Topping:
- Make the caramel. Melt the butter in a 8-10-inch cast iron skillet over medium-high heat. Add the brown sugar and cook, stirring constantly, until the mixture is bubbly and sugar has dissolved. You don't need to cook that long, just 2-3 minutes. Remove from the heat.
- Add pineapple and cherries. Starting at the outside of the pan, layer the pineapple in slightly overlapping concentric circles, rounded sides facing out. Tuck the cherries here and there and push down into the caramel. Set aside.
To Make The Cake:
- Heat oven. Heat the oven to 350°F.
- Sift. Sift together the flour, baking powder, and salt in a large bowl. Pour any leftover salt into the bowl.
- Cream butter. Place butter and sugar in the bowl of an electric mixer fitted with the paddle attachment. Beat on medium until very light in color. Scrape down sides of the bowl with a spatula.
- Add eggs. Add the egg yolks one at a time, beating after each addition. Add the vanilla and mix until smooth.
- Finish cake. On low speed add the dry ingredients in three batches alternating with the sour cream. Starting and ending with the dry ingredients. Beat only until everything is combined. Do not overmix. Spread the batter evenly over the pineapple.
- Bake. Bake on a parchment-lined baking sheet for 45-50 minutes, or until the top is springy to the touch, has a few shallow cracks in it and a toothpick inserted in the center comes out mostly clean (it's okay if a few moist crumbs stick to it).
- Flip. Let the cake cool for 15 minutes, then run a sharp knife around the inside edge of the skillet. Invert a large plate over the skillet and, using oven mitts, turn the skillet upside down to flip the cake over onto the plate. If the cake has cooled down too much, it may not release from the pan. If this happens, heat it for 2-3 minutes on the stovetop before attempting to turn it out.
- Serve. Let cake cool for another 30 minutes then serve warm slices of the cake with scoops of vanilla ice cream.
Notes
- Make-ahead instructions: You can assemble the cake through step 5, cover with plastic wrap and refrigerate up to a day in advance. Bake from cold, allowing for an extra 5-10 minutes bake time.
- Cast iron skillet: Use a 8-10 inch cast iron skillet. The 8-inch skillet will have a good chance of spilling over slightly so make sure to bake it on a parchment-lined baking sheet to catch any drips.
- Amarena cherries: These are Italian cherries that are sweet but with a tart edge. They can be found in the cocktail aisle of the grocery store or online.
- Fresh pineapple: You will only use about 1/2 of a medium pineapple (a little more if using a 10-inch skillet).
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Nutrition Information:
Yield: 10 Serving Size: 1Amount Per Serving: Calories: 150Total Fat: 14gSaturated Fat: 8gTrans Fat: 0gUnsaturated Fat: 5gCholesterol: 109mgSodium: 229mgCarbohydrates: 4gFiber: 0gSugar: 3gProtein: 3g
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