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4.31 from 83 votes
Top-down view of my pineapple upside down cake.
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Best Pineapple Upside Down Cake
Prep Time
20 mins
Cook Time
35 mins
Total Time
55 mins
 

My pineapple upside-down cake with caramelized fruit and a soft, buttery texture, is easy to prep in 20 minutes, and ready in an hour.

Course: Dessert
Cuisine: American
Servings: 12 people
Author: Gemma Stafford
Ingredients
For the Caramel
  • ½ cup (4 oz/115 g) butter
  • 1 ¼ cups (7½ oz/213 g) dark brown sugar
  • 2 cans (20 oz/567 g) sliced pineapple in juice (12 slices)
  • 10-13 maraschino cherries (stems removed)
For the Cake
  • 2 cups (10 oz/284 g) all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
  • ½ cup (4 oz/115 g) butter, softened
  • ½ cup (4 oz/115 g) granulated sugar
  • ⅓ cup (2 oz/57 g) dark brown sugar
  • 2 large eggs, at room temperature
  • ½ cup (4 fl oz/120 ml) whole milk
  • ½ cup (4 fl oz/120 ml) juice from the tinned pineapple
  • 1 teaspoon almond extract
Instructions
To Make The Caramel

  1. Preheat the oven to 350°F (180°C) and generously butter a 9x13-inch (23x33cm) baking pan. Set aside.

  2. In a small saucepan over medium-low heat, combine butter and brown sugar and simmer until the sugar is dissolved in about 2-3 minutes. Pour into the prepared baking pan.

  3. Drain the pineapple rings and reserve ½ cup (4floz/120ml) of juice. Arrange as many rings 4 x 3 or as you can fit in a single layer in the pan on top of the butter and brown sugar mixture.

  4. Place a maraschino cherry in the center of each pineapple ring.

To Make The Cake

  1. In a medium mixing bowl, combine the flour, baking powder and salt, mix well and set aside.

  2. Using a stand mixer (or electric hand mixer) cream together the butter with both sugars on high speed until light and fluffy, around 3 minutes.

  3. Whisk in one egg at a time until fully incorporated.

  4. Then mix in the dry ingredients until it comes together and resembles bread crumbs.

  5. Slowly stream in milk, reserved pineapple juice and almond extract. Mix until just combined and the batter is light and fluffy.

  6. Carefully spread the batter over the pineapples and then bake for 35-40 minutes, until a wooden skewer inserted into the center comes out clean.

  7. Let the cake cool for 10 minutes in the pan before inverting onto a serving tray.

  8. This cake is best the day it is made, but you can store leftovers covered at room temperature for up to 2 days.

Watch the Recipe Video!

Recipe Notes
  • Use Fresh Pineapple: Elevate with fresh fruit: You can use fresh pineapple for this recipe. Peel, core, and slice it to 1/2 inch thick. If you do this, replace the reserved can juice with ½ cup (4floz/120ml) of pineapple or orange juice in the cake batter.
  • Fresh Cherries: Upgrade with homemade glacé cherries: If you have fresh cherries, make homemade glacé cherries instead of using store-bought maraschino cherries for a more authentic flavor.
  • Perfect Inversion: Let it rest for easy flipping. Be sure to invert the cake while it is still warm, but not hot out of the oven. Let it rest for 10 minutes before flipping to prevent it from sticking or breaking.
  • Coconut Whipped Cream: Add a creamy, dairy-free topping. This cake is delicious served with coconut whipped cream. Refrigerate a can of full-fat coconut milk, scoop out the solids, discard the liquid, and whip until soft peaks form.
  • Pineapple Rum Twist: Infuse with tropical flavor. Make a pineapple rum upside-down cake by stirring 2 tablespoons of rum into the butter and brown sugar mixture before pouring it into the pan.