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Pineapple Upside Down Cake pinterest

Pineapple Upside Down Cake

This classic Pineapple Upside Down Cake features a perfect arrangement of caramelized pineapple rings and maraschino cherries atop a moist vanilla cake. A beloved American dessert for nearly a century that promises both visual appeal and comforting flavors.
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Course: Dessert
Cuisine: American
Keyword: Pineapple Upside Down Cake, Vintage Cake, Caramel Pineapple, Retro Dessert
Prep Time: 20 minutes
Cook Time: 45 minutes
Cooling Time: 10 minutes
Total Time: 1 hour 15 minutes
Servings: 8 slices
Calories: 320kcal

Equipment

  • 9-inch round cake pan (at least 2 inches high)
  • Mixing bowls
  • Electric Mixer
  • Serving plate

Ingredients

For the Topping

  • 1/4 cup unsalted butter substitute: coconut oil for dairy-free version
  • 2/3 cup packed brown sugar light or dark both work
  • 1 can pineapple rings in juice 20 oz, drained and juice reserved
  • 10-12 maraschino cherries patted dry
  • 1/4 cup chopped pecans optional

For the Cake

  • 1 1/3 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/3 cup unsalted butter softened
  • 1/2 cup reserved pineapple juice
  • 2 large eggs at room temperature
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1 teaspoon pure vanilla extract
  • 1/4 teaspoon almond extract optional

Instructions

  • Preheat your oven to 350°F (175°C). Use a 9-inch round cake pan with sides at least 2 inches high, or a well-seasoned cast iron skillet.
  • Melt 1/4 cup butter in your cake pan. Sprinkle the brown sugar evenly over the melted butter, gently tilting the pan to create a uniform layer.
  • Arrange pineapple rings decoratively on top of the brown sugar mixture. Place a maraschino cherry in the center of each pineapple ring and in any gaps between rings. Sprinkle chopped pecans in the remaining spaces if using.
  • In a medium bowl, whisk together flour, baking powder, and salt.
  • In a separate large bowl, cream the butter and sugar until light and fluffy (about 3 minutes with an electric mixer). Add eggs one at a time, beating well after each addition, then stir in vanilla extract and almond extract if using.
  • Gradually add the flour mixture to the butter mixture, alternating with reserved pineapple juice, beginning and ending with flour. Mix just until incorporated.
  • Carefully pour the batter over the pineapple arrangement, spreading gently to avoid disturbing your design. Tap the pan gently on the counter 2-3 times to release any air bubbles.
  • Bake in the preheated oven for 40-45 minutes, until a toothpick inserted in the center comes out clean and the top is golden brown.
  • Allow the cake to cool in the pan for exactly 10 minutes. Run a knife around the edge of the cake to loosen it, then place a serving plate upside down over the cake pan. Using oven mitts, carefully flip the cake and plate together in one smooth motion. Wait 30 seconds before removing the pan to allow the caramel to drizzle over the cake.

Notes

For best results, use room temperature ingredients to ensure proper incorporation of air into the batter. The timing of the flip is critical - too soon and the caramel will be too runny, too late and it may stick to the pan. Fresh pineapple can be substituted but should be patted dry thoroughly to prevent excess moisture. For a healthier version, you can reduce sugar in the cake batter by 1/4 cup and add cinnamon to enhance sweetness.

Nutrition

Calories: 320kcal | Carbohydrates: 52g | Protein: 3g | Fat: 12g | Saturated Fat: 7g | Cholesterol: 75mg | Sodium: 210mg | Fiber: 1g | Sugar: 38g | Vitamin C: 15mg | Iron: 8mg
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