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"A freshly baked Pineapple Upside Down Cake on a white plate with a slice served beside it, set on a wooden kitchen counter."

The Best Pineapple Upside Down Cake (Caramelized, From Scratch)

A classic pineapple upside down cake with caramelized brown sugar pineapple rings and maraschino cherries, baked over a buttery from-scratch vanilla batter and flipped warm to reveal a glossy, golden topping. No frosting, no decorating, no boxed mix.
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Prep Time 20 minutes
Cook Time 45 minutes
Total Time 1 hour 5 minutes
Servings: 10 Servings
Course: Dessert
Cuisine: American
Calories: 380
Ingredients Equipment Method Notes

Ingredients
  

Pineapple Topping
  • 4 tbsp unsalted butter
  • 3/4 cup light brown sugar packed
  • 1 can 20 oz sliced pineapple in juice drained, juice reserved
  • 10-12 maraschino cherries
Vanilla Cake Batter
  • 1 1/2 cups all-purpose flour spooned and leveled
  • 1 tsp baking powder
  • 1/4 tsp baking soda
  • 1/4 tsp salt
  • 1/2 cup unsalted butter room temperature
  • 3/4 cup granulated sugar
  • 2 large eggs room temperature
  • 1 tsp vanilla extract
  • 1/3 cup sour cream room temperature, full-fat (Daisy or Philadelphia Cream Style recommended)
  • 1/3 cup reserved pineapple juice from the can

Equipment

  • 1 10-inch cast iron skillet or 9-inch round metal pan Light-colored metal or cast iron only
  • 1 KitchenAid stand mixer or hand mixer For the batter
  • 1 Digital kitchen scale For accurate flour measurement
  • 1 Cake tester or toothpick For doneness check
  • 1 Wire rack For cooling after flipping
  • 1 Large heatproof serving plate Must be larger than the pan

Method
 

  1. Preheat oven to 350 degrees F.
    "A modern white wall oven with a digital display set to 350 degrees F, located in a bright and clean contemporary kitchen."
  2. Melt 4 tablespoons butter in a 10-inch cast iron skillet or 9-inch round cake pan over medium heat. Remove from heat. Sprinkle brown sugar evenly over the butter and stir into a rough paste.
    "A black cast iron skillet containing a bubbling mixture of melted butter and brown sugar, forming a thick, smooth caramel base on a wooden kitchen counter."
  3. Pat drained pineapple slices dry. Arrange over brown sugar: one ring in center, remaining rings around it. Press firmly. Place a maraschino cherry in each ring center and in gaps between slices.
    "A cast iron skillet prepared with a base of butter and brown sugar, topped with arranged pineapple rings and maraschino cherries in a beautiful pattern."
  4. Whisk flour, baking powder, baking soda, and salt in a bowl. Set aside.
    "Flour being sifted into a clear glass bowl, with a strainer resting on top, set on a wooden kitchen counter to prepare the dry ingredients for a cake."
  5. Beat butter and granulated sugar on medium-high for 3 minutes until pale and fluffy. Add eggs one at a time, scraping bowl between each. Add vanilla. Mix in sour cream on low.
    "A clear glass mixing bowl containing creamed butter, sugar, fresh eggs, vanilla extract, and sour cream, ready to be blended into a smooth cake batter."
  6. Add flour mixture in two additions, alternating with pineapple juice. Mix on low. Stop as soon as incorporated.
    "Pineapple juice being poured into a large glass mixing bowl containing flour and wet cake batter, demonstrating the process of combining ingredients."
  7. Pour batter gently over the fruit from the center outward. Spread carefully without disturbing the fruit.
    "A cast iron skillet filled with smooth, prepared cake batter, ready to be baked into a delicious pineapple upside-down cake on a kitchen counter."
  8. Bake 38 to 45 minutes until cake tester comes out clean and edges are golden.
    "A golden-brown pineapple upside-down cake baking inside a hot oven in a cast iron skillet."
  9. Rest in pan 5 to 10 minutes. Place large heatproof plate firmly over pan. Flip in one confident motion. Hold 5 seconds. Lift pan away slowly. Spoon any dripped caramel back over the cake.
    "A cast iron skillet placed upside down on a large white plate, just before being lifted to reveal a freshly baked pineapple upside-down cake."
  10. Serve warm or at room temperature. Dust with powdered sugar if desired.
    "A freshly baked, golden-brown Pineapple Upside Down Cake revealed after lifting the cast iron skillet, showcasing beautifully caramelized pineapple rings and cherries."

Notes

  • Do not use dark nonstick pans. They cause the brown sugar to burn.
  • Do not use uncooked fresh pineapple. Active bromelain enzyme can prevent the batter from setting.
  • Dry pineapple slices before arranging. Excess juice makes the caramel too thin.
  • Flip within 5 to 10 minutes of removing from oven. Too late and the caramel sticks.
  • Best served warm on day of baking. Reheat at 300 degrees F for 8 to 10 minutes if made ahead.