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old fashioned pineapple upside down cake
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Old-Fashioned Pineapple Upside-Down Cake

This old-fashioned pineapple upside-down cake features buttery vanilla cake and sticky caramelized pineapple. A classic, nostalgic dessert that’s simple, comforting, and always impressive.
Prep Time15 minutes
Cook Time40 minutes
Total Time55 minutes
Course: Dessert
Cuisine: American
Calories: 2104kcal

Ingredients

  • ¼ cup butter, melted
  • ½ cup brown sugar
  • 7 pineapple rings
  • 7 maraschino cherries (optional)
  • ½ cup granulated sugar
  • ¼ softened butter
  • 1 large egg
  • ½ cup milk
  • 1 cup all-purpose flour
  • 1 teaspoon baking powder

Instructions

  • Preheat the oven to 350°F (175°C). Pour the melted butter into an 8-inch round cake pan, then sprinkle the brown sugar evenly over the top.
  • Place the pineapple rings over the sugar mixture. Add a cherry to the center of each ring if you are using this ingredient. Set aside.
  • In a bowl, cream the softened butter and granulated sugar until light and fluffy. Beat in the egg, then stir in the milk. Add the flour and baking powder, mixing just until smooth.
  • Gently spread the batter over the pineapple layer, smoothing the top without disturbing the fruit.
  • Bake for 38–40 minutes, until golden, and a toothpick inserted into the center comes out clean.
  • Let the cake cool for 10 minutes, then carefully invert it onto a serving plate. Let the pan release naturally — don’t rush this part.

Video

Notes

Taste & Texture

Soft, moist vanilla cake
Sticky, caramelized pineapple topping
Buttery crumb with light tang
Sweet, nostalgic, and comforting

Storage, Freezing & Reheating

Fridge:
Store covered for up to 3 days.
Freezer:
Freeze the cake without the topping glaze for up to 2 months.
Reheat:
Microwave slices for 15–20 seconds, or warm in the oven at 300°F (150°C) until just heated through.
 

Nutrition

Calories: 2104kcal | Carbohydrates: 388g | Protein: 25g | Fat: 56g | Saturated Fat: 33g | Polyunsaturated Fat: 3g | Monounsaturated Fat: 15g | Trans Fat: 2g | Cholesterol: 301mg | Sodium: 519mg | Potassium: 1446mg | Fiber: 10g | Sugar: 283g | Vitamin A: 2075IU | Vitamin C: 38mg | Calcium: 555mg | Iron: 9mg