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pineapple upside down skillet cake

Pineapple Upside Down Skillet Cake

This Pineapple Upside Down Skillet Cake is soft, buttery, and full of caramelized pineapple flavor. Baked right in a cast iron skillet, it’s sweet, golden, and old-fashioned in the best way — a true comfort dessert that’s as fun to flip as it is to eat.
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Prep Time 15 minutes
Cook Time 40 minutes
Total Time 55 minutes
Servings: 8 servings
Course: Dessert
Cuisine: American, Classic Home Baking
Calories: 320
Ingredients Method Notes

Ingredients
  

For the topping:
  • ¼ cup unsalted butter
  • ½ cup packed brown sugar
  • 6 –8 pineapple slices fresh or canned, drained
  • 6 –8 maraschino cherries optional
  • For the cake batter:
  • 1½ cups all-purpose flour
  • 1½ tsp baking powder
  • ¼ tsp salt
  • ½ cup unsalted butter softened
  • ¾ cup granulated sugar
  • 2 large eggs
  • 1½ tsp vanilla extract
  • ½ cup milk room temperature

Method
 

Step 1: Caramelize the topping
  1. Preheat oven to 350°F (175°C). Place your 10-inch cast iron skillet on medium heat. Melt ¼ cup butter and stir in brown sugar until it turns glossy and bubbly. Turn off heat. Arrange pineapple slices over the caramel and place a cherry in each center.
Step 2: Make the batter
  1. In one bowl, whisk together flour, baking powder, and salt. In another bowl, cream butter and sugar until light and fluffy. Add eggs one at a time, then mix in vanilla. Alternate adding dry ingredients and milk until you get a smooth batter.
Step 3: Assemble and bake
  1. Pour the batter evenly over the caramelized pineapple in the skillet. Smooth the top with a spatula. Bake for 35–40 minutes or until golden and a toothpick comes out clean.
Step 4: The flip
  1. Let the cake cool for about 5 minutes. Run a knife around the edges, place a plate on top of the skillet, and carefully flip it over. Lift the skillet to reveal your glossy caramelized pineapple top.
Step 5: Serve and enjoy
  1. Serve warm with vanilla ice cream, whipped cream, or just as is. Every bite is buttery, tangy, and sweet all at once.

Notes

  • Let the cake rest for a few minutes before flipping so the topping sets.
  • Pat dry the pineapple slices to prevent a soggy topping.
  • If using fresh pineapple, slice it thin for even cooking.
  • For a twist, add a dash of cinnamon or a splash of dark rum to the caramel.
  • The cast iron skillet gives the best crust, but you can use a heavy ovenproof pan if needed.