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This pineapple upside down cake is a little old and new, a homemade classic with fresh pineapple and a rich caramel flavor.
This isn’t the pineapple upside down cake many of us grew up with: the one made with canned pineapple slices, maraschino cherries, and a box of yellow cake mix. This version is completely homemade, with fresh caramelized pineapple and a moist, buttery cake that bakes golden brown. It takes a little more effort than the retro classic, but the flavor and texture are worth it, and it’s still easy enough for a relaxed weekend.
Caramel may seem a little intimidating, but it’s really not. Just stay nearby and keep an eye on the color while cooking. I’ve included visual cues along the way so you know exactly when it will be ready.
Serve the cake warm or at room temperature, alone or with vanilla ice cream or light whipped cream. And if you’re feeling nostalgic, go ahead and add a maraschino cherry on top for fun.
Contents
What You’ll Need to Make Pineapple Upside Down Cake
To make this pineapple upside down cake recipe, you will need the following ingredients: fresh pineapple, all-purpose flour, baking powder, salt, unsalted butter, granulated sugar, large eggs, vanilla extract, and milk.
Step by step instructions
Step 1. Prepare the caramel. In a light-colored 12-inch skillet, combine sugar and water and stir to moisten. Bring to a boil over high heat and cook without stirring until the edges are golden brown, 4 to 5 minutes. Stir occasionally until uniformly amber.
Pro Tip: The caramel goes from perfect to burnt in seconds: stand right next to the stove as soon as it starts to turn golden. If it’s too dark, it will taste bitter; better to pull it a little earlier than to push too far.
Step 2. Add the butter and pineapple. Reduce the heat to low, carefully add the butter (it will bubble), then stir until smooth. Add the pineapple chunks and cook over medium-low heat, stirring occasionally, until lightly browned and softened, about 8 minutes.
Step 3. Transfer the filling. Use a slotted spoon to arrange the pineapple evenly in a prepared cake pan. Boil the caramel for another 2 to 3 minutes, until foamy and slightly thickened, then pour it evenly over the pineapple. Let cool slightly.
Step 4. Mix the dry ingredients. In a medium bowl, combine flour, baking powder and salt.
Step 5. Beat the butter, sugar and eggs. Next, in the bowl of a stand mixer fitted with the paddle attachment, beat the butter and sugar until light and fluffy, 2 to 3 minutes. Add the eggs one at a time, beating well and scraping the bowl after each one. Add the vanilla.
Pro Tip: Make sure your butter is at room temperature (soft enough to dent with your finger but not greasy). Too cold and it won’t cream properly; too hot and the dough may collapse.
Step 6. Add flour and milk. With the mixer on low, add the flour mixture in three additions, alternating with the milk in two additions, starting and ending with the flour. Mix until combined.
Step 7. Assemble and bake the cake. Spread the batter evenly over the pineapple and smooth the top with a spatula. Bake at 350°F for 45 to 50 minutes, until the top is golden brown and a toothpick comes out clean.
Step 9. Cool and invert. Leave to cool in the pan for 30 minutes on a wire rack. Run a knife around the edges, then invert onto a plate. Replace any sticking pineapple.
MORE Cakes That Celebrate Fruit
Pineapple Upside Down Cake
A buttery golden cake topped with caramelized pineapple: simple, classic and old-fashioned in the best way.
Ingredients
For the pineapple topping
- ¾ cup Powdered sugar
- ½ cup water
- 5 cups fresh pineapple, cut into 1-inch (2.5 cm) pieces
- 6 tablespoons butter
For the cake batter
- 1½ cups all-purpose flour, poured into a measuring cup and leveled
- 1½ teaspoons baking powder
- ½ teaspoon salt
- ¾ cup (1½ sticks) unsalted butter, at room temperature
- 1 cup Powdered sugar
- 3 large eggs
- 1½ teaspoons vanilla extract
- ¼ cup milk
- Vanilla ice cream or whipped cream, optional, to serve
Instructions
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Preheat the oven to 350°F (175°C) and place an oven rack in the middle position. Grease a 9-inch (23 cm) round cake pan with butter or nonstick cooking spray.
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Make the pineapple topping: In a 12-inch stainless steel or other light-colored pan (so you can easily monitor the color of the caramel), combine the sugar and water. Stir gently to moisten all the sugar. Bring to a boil over high heat and cook, without stirring, until the mixture begins to brown around the edges, 4 to 5 minutes. Once it begins to caramelize, swirl the pan occasionally until the caramel turns an even amber color, a few minutes more. Stay nearby at this point to monitor the color. You’ll know it’s close when you start smelling burnt sugar.
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Reduce the heat to low and carefully add the butter, it will bubble. Swirl the pan until the butter is melted and the mixture is smooth, then carefully add the pineapple chunks (remember you don’t want it to splatter as it’s very hot). Some of the caramel may harden at first; don’t worry, it will melt again as the pineapple warms up. Bring to a boil over high heat, then reduce the heat to medium-low and cook, stirring occasionally, until the pineapple is lightly browned and softened, about 8 minutes.
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Using a slotted spoon, transfer the pineapple to the prepared cake pan, arranging it in an even layer. (It’s easier to tilt the pan so the juices collect on one side, making it easier to extract the fruit.) Once you’ve removed all the pineapple, continue cooking the caramel over high heat for 2 to 3 minutes, or until it’s foamy and slightly thickened. If you scrape a wooden spoon across the bottom of the pan, the caramel should hold a line for 2 to 3 seconds before flowing back down. Pour the caramel sauce evenly over the pineapple. Let cool slightly while you prepare the cake batter.
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Prepare the cake batter: In a medium bowl, whisk together the flour, baking powder, and salt.
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In the bowl of an electric mixer fitted with the paddle attachment or paddle attachments, cream the butter and sugar on medium speed until light and fluffy, 2 to 3 minutes. Add the eggs one at a time, beating well and scraping down the sides after each addition. Add the vanilla. Don’t worry if the mixture seems a little curdled.
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With the mixer on low speed, add the flour mixture in three additions, alternating with the milk in two additions, starting and ending with the flour. Mix until combined.
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Pour the batter over the pineapple and smooth the top with an offset spatula.
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Bake the cake for 45 to 50 minutes, or until the top is golden brown and a toothpick inserted in the center comes out clean.
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Cool the cake in the pan on a rack for 30 minutes. Run a knife around the edge of the mold to loosen it, then invert it onto a serving dish. If a pineapple sticks to the pan, carefully return it to the pan. Serve warm or at room temperature. (A serrated knife is best for slicing through the pineapple layer.)
Remarks
- This cake is best served fresh the same day it is made, when the filling is shiny and the cake is tender. Store it at room temperature, ideally in a cake stand or covered with an inverted bowl to protect the filling (you can also cover lightly with foil).
- If you need to prepare it further, you can refrigerate the completely cooled inverted cake. Just be sure to cover it carefully to avoid damaging the trim. Before serving, let the cake come to room temperature. If you wish to serve it hot, individual slices can be gently warmed in the microwave.
- To freeze leftovers, wrap individual slices in plastic wrap and foil and freeze for up to 2 months. The caramel topping may lose some of its shine, but the flavor will still be delicious. Thaw at room temperature or reheat briefly in the microwave before serving.
Nutritional information
Per serving (10 servings)Calories: 448kilocaloriesCarbohydrates: 60gProtein: 4gFat: 22gSaturated fat: 13gCholesterol: 104mgSodium: 197mgFiber: 2gSugar: 43g
This website is written and produced for informational purposes only. I am not a certified nutritionist and the nutritional information on this site has not been evaluated or approved by a nutritionist or the Food and Drug Administration. Nutrition information is provided as a courtesy and should not be construed as a guarantee. Data is calculated via an online nutritional calculator, Edamam.com. Although I do my best to provide accurate nutritional information, these numbers should only be considered estimates. Various factors such as types of produce or brands purchased, natural fluctuations in fresh produce, and how ingredients are processed change the effective nutritional information of a given recipe. Additionally, different online calculators provide different results based on their own nutritional data sources and algorithms. To get the most accurate nutritional information in a given recipe, you should calculate the nutritional information with the actual ingredients used in your recipe, using your favorite nutritional calculator.
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