Double-Layer Old-Fashioned Pineapple Upside-Down Cake
A stunning, two-layer twist on the nostalgic Southern classic! Features a tender from-scratch cake base topped with a gorgeous, sticky brown sugar and pineapple ring glaze.
Equipment
- 2 (9-inch) round cake pans
- Stand mixer or electric hand mixer
- Wire cooling rack
Ingredients
- Topping:
- 1/2 cup 1 stick unsalted butter, melted
- 1 cup light or dark brown sugar packed
- 1 20 oz can pineapple slices in juice (reserve 1/4 cup juice)
- 1 jar maraschino cherries stems removed
- Cake Batter:
- 2 cups all-purpose flour
- 2 tsp baking powder
- 1/2 tsp salt
- 1/2 cup 1 stick unsalted butter, softened
- 1 cup granulated sugar
- 2 large eggs room temperature
- 2 tsp vanilla extract
- 1/2 cup whole milk room temperature
- 1/4 cup reserved pineapple juice
Instructions
- Preheat oven to 350°F (175°C). Grease the sides of two 9-inch round cake pans.
- Pour the 1/2 cup melted butter evenly into the bottom of one cake pan. Sprinkle the brown sugar evenly over the butter.
- Pat the pineapple slices and cherries dry. Arrange the pineapple rings over the brown sugar in a single layer. Place a cherry in the center of each ring.
- In a medium bowl, whisk together the flour, baking powder, and salt.
- In a large bowl, beat the softened butter and granulated sugar until light and fluffy (about 3 mins).
- Add the eggs one at a time, beating well. Stir in the vanilla extract.
- Combine the milk and reserved pineapple juice. Alternate adding the dry ingredients and the milk mixture to the butter, mixing just until combined.
- Divide the batter evenly between the two pans, carefully spreading it over the fruit in the first pan, and smoothing the plain batter in the second pan.
- Bake for 30-35 minutes until a toothpick comes out clean.
- Remove from oven. Let the plain cake cool completely in its pan. Let the pineapple layer rest for exactly 10 minutes, then invert it onto a wire rack to cool.
- Once completely cool, place the plain cake on a serving platter. Carefully place the pineapple layer directly on top. Slice and serve!
Notes
The Flip: Do not skip the 10-minute wait before flipping the pineapple layer. It allows the caramel to thicken slightly without hardening to the pan. Assembly: If the plain bottom layer has a dome, trim it flat with a serrated knife before stacking so the top layer doesn't slide.
