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5.0 from 6 votes

Grilled Pineapple Upside-Down Skillet Cake

My mom used to make a warm classic pineapple upside-down cake made with yellow cake mix that was simply sinful. This recipe is inspired by mom’s cake, but made from scratch and is baked in a cast-iron skillet and topped with fresh grilled pineapples.

Prep Time
10 mins
Cook Time
10 mins
Total Time
1 hr 2 mins
Servings: 8 to 10 Servings
Calories: 454 kcal
Course: Dessert
Cuisine: American

Ingredients

  • Fresh pineapple slices
  • 1 tablespoon vegetable oil
  • 11 tablespoons unsalted butter divided
  • ¾ cup packed light brown sugar
  • 1/3 cup maraschino cherries without stems
  • 1½ cups all-purpose flour
  • 1½ teaspoons baking powder
  • ¼ teaspoon salt
  • ¾ cup granulated sugar
  • 1 teaspoon pure vanilla extract
  • 2 eggs
  • ½ cup milk

Instructions

    Cup of Yum
  1. Lightly brush both sides of pineapple rings with vegetable oil and grill them, turning once, until lightly charred, about 3 minutes per side. Let cool and set aside.
  2. Melt 3 tablespoons of butter in a 10-inch cast-iron skillet. Add brown sugar and cook while stirring, until sugar is melted and begins to bubble. Remove from heat and cool. Once cool, arrange the pineapple slices in the melted sugar and add cherries pineapple slices. Set aside.
  3. Preheat oven to 350 degrees F.
  4. In a bowl sift the flour, baking powder, and salt.
  5. In a separate bowl, beat remaining 8 tablespoons butter and the granulated sugar until creamy. Add the vanilla and then the eggs, one at a time, beating until smooth.
  6. Add the flour mixture little by little as you slowly stir in the milk. Do not over mix: stir just until the flour is incorporated into the batter.
  7. Pour cake batter over fruit in skillet, using a spoon to gently spread it to the edge.
  8. Bake for 30 to 40 minutes, until a toothpick inserted in the middle comes out clean.
  9. Remove from oven. Let cool about 5 to 10 minutes—do not let cool too long or it will stick in your skillet. Place a cake platter over skillet and, wearing oven mitts, carefully flip the cake onto the cake platter.

Notes

  • The cake is not grilled, but the fresh pineapple slices are. Grilled pineapple gives them a candied caramel flavor. The key is not to char the pineapple, but to just achieve golden brown delicious coloring on your fruit.

Nutrition Information

Calories 454kcal (23%) Carbohydrates 68g (23%) Protein 5g (10%) Fat 19g (29%) Saturated Fat 12g (60%) Cholesterol 84mg (28%) Sodium 105mg (4%) Potassium 250mg (7%) Fiber 2g (8%) Sugar 47g (94%) Vitamin A 609IU (12%) Vitamin C 36mg (40%) Calcium 91mg (9%) Iron 2mg (11%)

Nutrition Facts

Serving: 8to 10 Servings

Amount Per Serving

Calories 454

% Daily Value*

Calories 454kcal 23%
Carbohydrates 68g 23%
Protein 5g 10%
Fat 19g 29%
Saturated Fat 12g 60%
Cholesterol 84mg 28%
Sodium 105mg 4%
Potassium 250mg 5%
Fiber 2g 8%
Sugar 47g 94%
Vitamin A 609IU 12%
Vitamin C 36mg 40%
Calcium 91mg 9%
Iron 2mg 11%

* Percent Daily Values are based on a 2,000 calorie diet.

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