This Pineapple Upside Down Cake is an old-fashioned dessert featuring sweet pineapple rings, buttery brown sugar, and optional maraschino cherries baked beneath a soft, moist vanilla cake. Made from scratch in a 12-inch cast-iron skillet, this classic recipe creates a beautifully caramelized fruit topping when the finished cake is inverted onto a serving plate.
Inspired by Ree Drummond’s Pioneer Woman recipe, this homemade pineapple upside down cake combines simple pantry ingredients with a traditional skillet-baking method. The pineapple juice adds extra fruit flavor to the batter, while the brown sugar and melted butter form a rich, glossy topping.
Why You’ll Love This Pineapple Upside Down Cake
- Made from scratch: Uses flour, sugar, butter, eggs, milk, and vanilla.
- Classic caramelized topping: Brown sugar and butter surround sweet pineapple rings.
- Cast-iron preparation: A skillet works for both preparing the topping and baking the cake.
- Beautiful presentation: Pineapple rings and cherries create a decorative finish.
- Perfect served warm: Delicious for family dinners and special occasions.
How to Make Pineapple Upside Down Cake
Start by preheating your oven to 350°F.
Combine the flour, baking powder, salt, granulated sugar, softened butter, shortening, milk, eggs, vanilla, and reserved pineapple juice. Beat until combined, leaving a few small lumps in the batter.
Melt the remaining butter in a 12-inch cast-iron skillet. Sprinkle the brown sugar evenly over the butter without stirring, then arrange the pineapple rings on top. Add maraschino cherries to the centers if desired.
Carefully spread the cake batter over the pineapple topping.
Bake for 30–40 minutes, until a toothpick inserted into the center comes out clean.
Run a knife around the edge of the skillet, place a large serving plate over the top, and carefully invert the cake while it is still warm.
A well-seasoned 12-inch cast-iron skillet is especially useful because it allows you to prepare the topping and bake the cake in the same pan.
Tips for the Best Results
Drain the pineapple rings before arranging them in the skillet, reserving the juice needed for the batter.
Use a serving plate larger than the skillet, and protect your hands when inverting the hot cake.
Let the cake cool slightly before cutting into eight wedges. Serve warm for the best combination of tender cake and buttery pineapple topping.
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Pineapple Upside Down Cake
The Pioneer Woman’s old-fashioned Pineapple Upside-Down Cake delivers a really good take on the dessert classic: pineapple upside down cake be Ree Drummond.
- Total Time: 1:00
- Yield: 8 1x
Ingredients
- 2 1/2 cups all-purpose flour
- 1 tablespoon baking powder
- 1 teaspoon salt
- 2 cups granulated sugar
- 1 stick unsalted butter, at room temperature
- 1/4 cup vegetable shortening
- 1 1/2 cups whole milk
- 2 large eggs
- 2 teaspoons vanilla extract
- 1 20 –ounce can sliced pineapple,
- 2 tablespoons juice reserved (drink the rest!)
- 1 1/3 cups packed light brown sugar
- Maraschino cherries, stemmed (optional)
Instructions
- Preheat the oven to 350 degrees F. Make the cake batter: Combine the flour, baking powder, salt, granulated sugar, 1/2 stick butter, the shortening, milk, eggs, vanilla and 2 tablespoons pineapple juice in a large bowl. Beat with a mixer on medium speed until well combined. (There will still be a few small lumps in the batter.) Set aside.
- Melt the remaining 1/2 stick butter in a 12-inch cast-iron skillet over medium heat; swirl to thoroughly coat the skillet. Sprinkle the brown sugar over the butter, making sure it’s evenly distributed-you want the entire surface of the butter to be covered in brown sugar. Do not stir. As soon as the sugar dissolves, remove from the heat and layer the pineapple slices over the top. If desired, place maraschino cherries in the centers of the pineapple slices.
- Pour the batter evenly over the pineapple slices and gently spread to even out the top. Bake the cake 30 to 40 minutes, or until a toothpick inserted into the center comes out clean.
- Immediately run a knife around the edge of the cake, then put a plate upside down on top of the skillet. Carefully invert the skillet so the cake is turned onto the plate. It should come out pretty easily; if bits of cake stick to the skillet, use a small knife to patch it together. Let cool slightly before cutting into wedges. It’s best served warm.
- Prep Time: :20
- Cook Time: :40
- Category: Desserts
- Method: Baked
Nutrition
- Serving Size: 8