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Pineapple Upside-Down Cake

This recipe creates a classic Pineapple Upside-Down Cake, starting with a rich, caramelized brown sugar and pineapple base cooked directly in a cast-iron skillet. A tender cake batter is poured over the fruit and baked until golden. The cake is then inverted, revealing a beautiful, glistening pineapple top, offering a delightful balance of sweet and tangy flavors.
Cook Time 25 minutes
Total Time 1 hour 15 minutes
Course lunch/dinner, Snack
Cuisine American
Servings 8 people
Calories 2016 kcal

Equipment

  • 1 Cast-iron skillet 10-inch size recommended
  • 1 Stand Mixer With paddle attachment
  • 2 Mixing Bowls For wet and dry 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

1. Ensure pineapple is thoroughly drained to prevent a soggy cake base. Press out excess liquid from both sliced and crushed pineapple.2. For best results, ensure your egg and milk are at room temperature. This helps them combine more smoothly with the other ingredients, leading to a more uniform cake batter and a tender crumb.3. When melting the brown sugar and butter, cook until just melted and syrupy, being careful not to burn it. This caramel layer is crucial for flavor and appearance.4. When baking, if the top browns too quickly, a loose foil tent will prevent over-browning while the interior cooks through. Cool time before inverting is essential for the cake to set and release cleanly.