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 mins
Cook Time40 minutes mins
Total Time55 minutes mins
Course: Dessert
Cuisine: American
Calories: 2104kcal
- 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
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.
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.
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