Old Fashioned Pineapple Upside Down Cake
This Old Fashioned Pineapple Upside Down Cake is a classic homemade dessert with a buttery brown sugar caramel topping, juicy pineapple slices, and bright maraschino cherries. The tender vanilla cake bakes directly over the fruit, then is flipped to reveal a beautiful golden pineapple topping.
- Prep Time: 20 minutes
- Cook Time: 45 minutes
- Total Time: 1 hour 5 minutes
- Yield: 10 servings
- Category: Dessert
- Method: Oven
- Cuisine: American
- Diet: Vegetarian
Ingredients
- For the Caramel Topping:
- 1/2 cup (1 stick) unsalted butter, melted
- 1 cup packed light brown sugar
- 1 can (20 oz) pineapple slices, juice reserved
- 12–15 maraschino cherries, stems removed
- For the Cake Batter:
- 2 cups all-purpose flour
- 1 1/4 cups granulated sugar
- 3 teaspoons baking powder
- 1/2 teaspoon salt
- 1/2 cup (1 stick) unsalted butter, softened to room temperature
- 2 large eggs, room temperature
- 1 cup reserved pineapple juice
- 1 1/2 teaspoons vanilla extract
Instructions
- Preheat the oven to 350°F (175°C). Grease a 9-inch round cake pan or deep 9-inch skillet.
- Pour the melted butter evenly into the bottom of the prepared pan. Sprinkle the brown sugar evenly over the butter.
- Arrange the pineapple slices over the brown sugar and place a maraschino cherry in the center of each pineapple slice. Set aside.
- In a medium bowl, whisk together the flour, granulated sugar, baking powder, and salt.
- In a separate large bowl, beat the softened butter until creamy. Add the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
- Gradually add the dry ingredients to the butter mixture, alternating with the reserved pineapple juice. Mix just until combined.
- Carefully spread the cake batter evenly over the pineapple slices and cherries.
- Bake for 40–50 minutes, or until the cake is golden brown and a toothpick inserted into the center of the cake comes out clean.
- Let the cake cool in the pan for 10–15 minutes. Do not allow it to cool completely in the pan, as the caramel topping may stick.
- Place a serving plate over the cake pan. Carefully but quickly invert the pan onto the plate. Allow the pan to sit upside down for a few seconds before lifting it away.
- If any pineapple or cherries remain in the pan, carefully place them back onto the cake.
- Serve warm or at room temperature.
Notes
- Reserve the pineapple juice before draining the pineapple slices because it is used in the cake batter.
- Make sure the cake is inverted while still warm so the caramel topping releases more easily.
- Use a deep cake pan to prevent the batter from overflowing during baking.
- For an even fruit pattern, arrange the pineapple slices and cherries carefully before adding the batter.
- Let the cake rest for about 10–15 minutes after baking, but avoid leaving it in the pan for too long.
- Store covered at room temperature for up to 2 days or refrigerate for longer storage.