This delightful sinfully dairy pineapple upside down cake features a soft, buttery base topped with caramelized pineapples and cherries in a rich brown sugar glaze. As the juices from the fruit mingle with the cake during baking, they infuse it with an irresistible flavor and moist texture. A beloved classic that utilizes canned pineapple and maraschino cherries, this retro dairy dessert is perfect for any occasion and is served in its unique inverted presentation.

Pineapple Upside Down Cake (D)

Dairy

Yield: Serves 8-10

Ingredients:

For the Topping:

• 1/4 cup (4 tablespoons; 56g) unsalted butter, melted
• 1/2 cup (100g) packed brown sugar (light or dark)
• 8–10 pineapple slices
• 15–20 maraschino cherries

For the Cake:

• 1 and 1/2 cups (177g) cake flour
• 1 teaspoon baking powder
• 1/4 teaspoon baking soda
• 1/2 teaspoon salt
• 6 tablespoons (85g) unsalted butter, softened
• 3/4 cup (150g) granulated sugar
• 2 large egg whites, at room temperature
• 1/3 cup (80g) sour cream, at room temperature
• 1 teaspoon pure vanilla extract
• 1/4 cup (60ml) pineapple juice, at room temperature (can use leftover juice from canned pineapple)
• 2 tablespoons (30ml) milk, at room temperature

Method:

1. Preheat your oven to 350°F (177°C).
2. Start with the topping: Pour the melted butter into an ungreased 9×2-inch pie dish or round cake pan (ensure it’s 2 inches deep). Evenly sprinkle the brown sugar over the butter. Pat the pineapple slices with a clean towel to remove excess moisture, as wet fruit can cause overflow during baking. Arrange about 6-7 pineapple slices and all the cherries over the brown sugar, optionally halving some rings to create a decorative arrangement along the edges. Chill the pan in the refrigerator briefly while you prepare the batter.
3. For the cake batter, whisk together the cake flour, baking powder, baking soda, and salt in a separate bowl, then set aside.
4. Using a handheld or stand mixer with a paddle attachment, beat the softened butter until creamy. Gradually add the sugar and beat until well combined. Incorporate the egg whites, then add the sour cream and vanilla extract. Once combined, gradually mix in the dry ingredients, followed by the pineapple juice and milk, beating just until combined. Take care not to over-mix; a few lumps are fine.
5. Remove the topping from the refrigerator and pour the cake batter evenly over it.
6. Bake for 43-48 minutes, covering the top with aluminum foil halfway through to prevent burning. The cake is ready when a toothpick inserted in the center comes out mostly clean, with a few moist crumbs acceptable. It’s normal for the cake to rise and make contact with the foil since you’ll be serving it upside down.
7. After baking, let the cake cool for about 20 minutes on a wire rack. Carefully invert it onto a serving platter; it’s fine if some juices run over the edges. While you can enjoy it warm, allowing it to completely cool at room temperature before slicing will yield the best results. Avoid refrigerating the cake to speed up cooling, as this can affect its texture.
8. Store any leftovers in the refrigerator for up to 3 days or freeze for up to 3 months. If freezing, thaw at room temperature, as the topping arrangement may not hold up if the entire cake is frozen.