Description
Classic pineapple upside down cake with caramelized brown sugar topping, juicy pineapple rings, and maraschino cherries over tender vanilla cake. This easy retro dessert is stunning and delicious.
Ingredients
Scale
For the Topping:
- ¼ cup (½ stick) unsalted butter
- ⅔ cup packed light brown sugar
- 7–8 canned pineapple rings, drained and patted dry
- 7–8 maraschino cherries, drained and patted dry
For the Cake:
- 1½ cups all-purpose flour
- 1½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup (1 stick) unsalted butter, softened
- ¾ cup granulated sugar
- 2 large eggs, room temperature
- 1 teaspoon pure vanilla extract
- ½ cup whole milk, room temperature
Instructions
- Preheat Oven: Preheat your oven to 350°F (175°C). Position rack in center of oven.
- Prepare Topping: In a medium saucepan over medium heat, melt ¼ cup butter. Add brown sugar and stir constantly until sugar dissolves and mixture is smooth and bubbly, about 2-3 minutes. Pour this caramel mixture into the bottom of a 9 or 10-inch round cake pan, tilting to coat the bottom evenly.
- Arrange Fruit: Place pineapple rings in a single layer over the caramel mixture. You should fit 7 rings in a 9-inch pan (one in center, six around it) or 8 in a 10-inch pan. Place a maraschino cherry in the center of each pineapple ring, pressing gently into the caramel. Set aside.
- Mix Dry Ingredients: In a medium bowl, whisk together flour, baking powder, and salt. Set aside.
- Cream Butter and Sugar: In a large bowl using an electric mixer, beat softened butter and granulated sugar on medium-high speed for 3-4 minutes until light, fluffy, and pale yellow. Scrape down bowl sides as needed.
- Add Eggs and Vanilla: Add eggs one at a time, beating well after each addition until fully incorporated. Beat in vanilla extract. The mixture should be smooth and creamy.
- Alternate Dry and Wet: With mixer on low speed, add flour mixture in three additions, alternating with milk in two additions. Begin and end with flour (flour-milk-flour-milk-flour pattern). Mix just until combined after each addition—don’t overmix or cake will be tough.
- Pour Over Pineapple: Carefully spoon cake batter over the arranged pineapple and cherries, spreading gently and evenly to cover. The batter is thick—use your spatula to spread it carefully without disturbing the fruit pattern.
- Bake: Bake for 40-45 minutes, until a toothpick inserted in the center comes out clean or with just a few moist crumbs. The cake should be golden brown and spring back when gently pressed. The edges may pull away slightly from the pan.
- Cool Briefly: Remove from oven and let cool in the pan on a wire rack for exactly 10 minutes. This cooling time is crucial—too short and the cake falls apart, too long and it sticks to the pan.
- The Big Flip: After 10 minutes, run a thin knife around the edges to loosen. Place your serving plate upside down on top of the cake pan. Using oven mitts, hold both plate and pan firmly together and quickly but confidently flip them over. Carefully lift the pan off, revealing your beautiful pineapple topping. If any fruit sticks, simply lift it off and replace it on the cake.
- Cool and Serve: Let cake cool for at least 15-20 minutes before slicing. Serve warm, room temperature, or chilled. Delicious with vanilla ice cream or whipped cream!
Notes
- Pan size matters: Use exactly 9 or 10-inch round pan for proper fruit arrangement and baking time
- Don’t skip the 10-minute cooling: This timing is crucial for successful flipping
- Drain fruit well: Excess moisture prevents proper caramelization
- Room temperature ingredients: Ensure eggs, butter, and milk are room temp for smooth mixing
- Cast iron option: A 10-inch cast iron skillet works beautifully and can go straight to the table
- Check doneness: Toothpick should come out clean; don’t overbake or cake becomes dry
- Prep Time: 15 minutes
- Cook Time: 45 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 slice (based on 10 servings)
- Calories: 340
- Sugar: 35g
- Sodium: 150mg
- Fat: 14g
- Saturated Fat: 8g
- Unsaturated Fat: 5g
- Trans Fat: 0g
- Carbohydrates: 52g
- Fiber: 1g
- Protein: 4g
- Cholesterol: 75mg