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Pineapple Upside Down Cake

This stunning Pineapple Upside Down Cake features caramelized pineapple rings on top, creating a sweet and impressive dessert that's perfect for any occasion.
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Prep Time 15 minutes
Cook Time 45 minutes
Total Time 1 hour
Servings: 12 slices
Course: Dessert, Snack
Cuisine: American
Calories: 290
Ingredients Method Notes

Ingredients
  

For the Topping
  • 1/4 cup unsalted butter Melt in the skillet
  • 2/3 cup packed brown sugar For caramelizing the pineapple
  • 1 can (20 oz) pineapple slices, drained Canned for convenience
  • 10-12 pieces maraschino cherries For decoration
  • pecan halves Optional but recommended for added crunch
For the Cake
  • 1 and 1/2 cups all-purpose flour For cake batter
  • 1 and 1/2 teaspoons baking powder Ensure it's fresh for best results
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter, softened At room temperature
  • 3/4 cup granulated sugar For sweetness
  • 2 large eggs Room temperature for easier mixing
  • 1 teaspoon vanilla extract Use real vanilla for best flavor
  • 1/2 cup whole milk At room temperature

Method
 

Making the Topping
  1. Melt butter in your cast-iron skillet over medium heat. Watch it carefully—don't let it brown.
  2. Add brown sugar and stir until completely dissolved for about 2-3 minutes.
  3. Remove from heat once the sugar dissolves completely.
  4. Let the butter-sugar mixture cool for 5 minutes before arranging the pineapple.
  5. Arrange pineapple rings and cherries in the pan, tucking pecans between the rings if desired.
Making the Cake Batter
  1. Whisk together flour, baking powder, and salt in a medium bowl. Set aside.
  2. Beat softened butter in a large bowl for 2 minutes, then gradually add granulated sugar.
  3. Cream together until light and fluffy for 3-4 minutes.
  4. Add eggs one at a time, mixing well after each addition, and then mix in vanilla extract.
  5. Add half the flour mixture to the batter, then pour in whole milk, mixing gently.
  6. Add the remaining flour mixture, mixing just until combined. Don't overmix.
Baking Process
  1. Pour batter carefully over the arranged pineapple and spread it evenly.
  2. Preheat your oven to 350°F (175°C) and bake for 45-50 minutes.
  3. Test with a toothpick; it should come out clean when done.
  4. Cool in the pan for 10 minutes before flipping onto a serving plate.

Notes

Serve warm with vanilla ice cream or whipped cream. For variations, consider using fresh pineapple or adding a cream cheese glaze.