Description

This classic Pineapple Upside-Down Cake features a caramelized brown sugar and butter topping with juicy pineapple slices and maraschino cherries, layered under a moist, tender vanilla cake batter infused with pineapple juice and buttermilk. Perfect for a nostalgic dessert that is both visually stunning and deliciously sweet.

Ingredients

Topping

1/4 cup (1/2 stick) butter
1/2 cup brown sugar, packed
1 can (20 oz) pineapple slices, drained (reserve juice)
10-12 maraschino cherries (or as desired)

Cake Batter

1 1/2 cups all-purpose flour
1 teaspoon baking powder
1/2 teaspoon baking soda
1/4 teaspoon salt
1/2 cup (1 stick) butter, softened
1 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
1/2 cup pineapple juice (from canned pineapple)
1/2 cup buttermilk (or regular milk)

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Instructions

Prepare the Topping: Preheat the oven to 350°F (175°C). In a 9-inch round cake pan, melt 1/4 cup of butter in the oven. Once melted, sprinkle the brown sugar evenly over the butter. Arrange the pineapple slices in a circular pattern over the sugar, placing a maraschino cherry in the center of each pineapple ring.
Prepare the Cake Batter: In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. In a separate large bowl, cream the softened butter and granulated sugar together until light and fluffy, about 2 to 3 minutes. Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
Combine Wet and Dry Ingredients: Gradually add the dry ingredients to the creamed butter mixture, alternating with the pineapple juice and buttermilk. Begin and end with the dry ingredients, mixing just until combined to avoid overmixing.
Assemble the Cake: Pour the batter evenly over the arranged pineapple slices in the prepared cake pan. Smooth the top gently with a spatula to ensure even baking.
Bake: Bake the cake in the preheated oven for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean and the cake surface is golden brown.
Cool and Invert: Let the cake cool in the pan for 10 minutes. Run a knife around the edges to loosen it. Place a plate on top of the pan and carefully invert the cake onto the plate. Allow the cake to cool completely before serving to set the topping.

Notes

For a richer flavor, you can caramelize the brown sugar thoroughly but be careful not to burn it.
If buttermilk is unavailable, regular milk with a teaspoon of lemon juice or vinegar can be used as a substitute.
Ensure the cake cools slightly before inverting to prevent the topping from sliding off.
This cake can be served warm or at room temperature and pairs wonderfully with whipped cream or vanilla ice cream.