The Best Pineapple Upside Down Cake - Like Momma Used To Make
There are some desserts that don't just taste good — they take you somewhere. Pineapple upside down cake is one of them. One look at those golden caramelized pineapple rings resting on a perfectly browned, buttery cake and you're instantly transported to Momma's kitchen, where the oven was always warm and something sweet was never far away. This version stays true to everything that made the classic great — a rich brown sugar caramel base, fresh pineapple, and a hint of dark rum and cardamom that add just enough sophistication to feel special without straying from its roots. Baked in a cast iron skillet the way it was always meant to be, this is the cake that earns a handwritten recipe card and gets passed down for a reason.
INGREDIENTS
1/4 cup butter
3/4 cup light brown sugar
1 tablespoon pineapple juice
1 tablespoon dark rum (optional)
1/2 small fresh pineapple - peeled, cored, and sliced
1 1/2 cups all-purpose flour
1/8 teaspoon ground cardamom
1/2 teaspoon salt
2 teaspoons baking powder
1/2 cup white sugar
1 egg
1/2 cup cold milk
STEPS
Preheat the oven to 400 degrees F (200 degrees C).
Melt 1/4 cup butter in a 12-inch cast iron skillet over medium-low heat. Stir in brown sugar, pineapple juice, and dark rum. Cook over medium-low heat until sugar is dissolved and mixture is bubbling, about 5 minutes.
Remove from heat and spread pineapple slices in a layer over the brown sugar mixture, completely covering the mixture. Set skillet aside.
Melt 1/2 cup butter in small skillet over low heat until the butter begins to brown and release a nutty fragrance, about 5 minutes. Watch carefully, butter burns easily. Remove from heat and let cool for 10 minutes.
Whisk together flour, cardamom, salt, baking powder, and white sugar in a large bowl. Whisk in egg and cold milk until just combined. Pour in melted butter and stir to mix thoroughly.
Pour batter over the pineapple slices in the skillet; spread evenly to cover.
Bake in preheated oven until the cake begins to bubble around the edges, the top is browned, and a toothpick inserted into the center comes out clean, about 30 to 35 minutes. Let cool in the skillet for 10 minutes.
Loosen the cake from the skillet by running a knife around the inside edge of the cake. Invert a large plate over the top of the skillet and flip over, releasing the cake to show the pineapple slices on top.