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Pineapple Upside-Down Cake

This recipe creates a classic Pineapple Upside-Down Cake featuring a glistening caramelized pineapple and crushed pineapple topping baked beneath a moist, tender cake. Prepared in a cast-iron skillet, it's inverted after baking to reveal its beautiful presentation, offering a delightful balance of sweet fruit and rich cake.
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Cook Time 25 minutes
Total Time 1 hour 15 minutes
Course lunch/dinner, Snack
Cuisine American
Servings 8 people
Calories 2016 kcal

Equipment

  • 1 10-inch Cast-Iron Skillet
  • 1 Stand Mixer with paddle attachment
  • 2 Mixing Bowls For dry and wet ingredients
  • 1 Whisk
  • 1 Cutting Board or Large Plate For inverting the cake

Ingredients
  

Main

  • 2 tablespoons unsalted butter
  • 1/2 cup lightly packed dark brown sugar
  • One 20-ounce can sliced pineapple drained and juice reserved
  • One 20-ounce can crushed pineapple drained and juice reserved
  • 1 1/3 cups all-purpose flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon fine salt
  • 1/2 cup whole milk
  • 2 teaspoons pure vanilla extract
  • 1/4 cup reserved pineapple juice from the cans
  • 3/4 cup granulated sugar
  • 1/2 cup unrefined coconut oil
  • 1 large egg

Instructions
 

  • Preheat the oven to 350 degrees F.
  • For the pineapple: In a 10-inch cast-iron skillet over medium heat, melt the butter and add the brown sugar. Cook, stirring constantly, until the sugar melts, about 2 minutes. Remove from the heat and arrange the pineapple slices in the skillet. Fill in the spaces with the crushed pineapple. Set aside.
  • For the cake: Meanwhile, combine the cake ingredients in this fashion: In one bowl, whisk together the flour, baking powder and salt. In bowl number 2, combine the milk, vanilla extract and 1/4 cup of the reserved pineapple juice.
  • In the bowl of a stand mixer fitted with a paddle attachment, combine the granulated sugar and coconut oil on medium speed until thick and creamy, about 3 minutes. Beat in the egg. Add half of the flour mixture and mix on low until just combined. Add the milk mixture and stir until just combined. Add the rest of the flour and mix until combined, about 1 minute.
  • Pour the batter over the pineapple slices in the skillet and spread evenly. Bake until the top is golden brown and a toothpick comes out clean when inserted, 25 to 35 minutes, checking after 20 minutes to make sure the top isn't getting too brown. If it is, cover loosely with aluminum foil.
  • Let cool for 15 minutes. Cover with a cutting board or large plate and invert the cake. Ta daaaaaaa, you are ready to eat!

Notes

For a perfect caramel topping, ensure the butter and brown sugar mixture is gently melted and well-combined without burning. The use of coconut oil contributes to a unique texture; ensure it's properly creamed with sugar. When adding dry and wet ingredients to the cake batter, mix just until combined to prevent overdeveloping gluten, which can lead to a tough cake. The critical step for a beautiful upside-down cake is the inversion: allow it to cool for the recommended 15 minutes before inverting onto a plate to ensure the caramel sets slightly and the cake releases cleanly without sticking, keeping the pineapple topping intact and glossy.