Pineapple upside-down cake is traditionally a skillet cake, and a 10-inch cast iron skillet is still the most practical pan for it. The butter and brown sugar for the topping are melted in the skillet on the stove, the pineapple rings are laid straight into it, the batter goes on top, and the same pan moves to the oven.
Cast iron holds heat well, so the sugar underneath the fruit cooks into a glossy caramel instead of staying pale and wet, and the heavy pan gives the cake an even golden edge. The batter is a simple creamed butter cake, with some of the juice from the pineapple can replacing part of the milk so the fruit flavor carries through the crumb.
Two details make the turn-out clean. Drain the pineapple and pat it dry so the topping is not watery, and invert the cake 10 minutes after it leaves the oven, while the caramel is still soft enough to let go of the pan. The same skillet also makes this cast iron skillet cornbread.

Cast Iron Skillet Pineapple Upside-Down Cake
Ingredients
Method
- Heat the oven to 350°F with a rack in the center. Drain the pineapple, saving 1/4 cup of the juice for the batter, and pat 7 slices dry with paper towels. Pat the cherries dry, if using.
- Melt the 4 tablespoons butter in a 10-inch cast iron skillet over medium-low heat, tilting the pan so the butter also coats the sides. Take the skillet off the heat.
- Sprinkle the 2/3 cup brown sugar evenly over the melted butter. Do not stir.
- Lay one pineapple slice in the center and six around it in a single layer. Put a cherry in the hole of each slice. Set the skillet aside.
- In a medium bowl, whisk together the 1 1/2 cups flour, the baking powder and the salt. In a measuring cup, combine the 1/4 cup milk and 1/4 cup reserved pineapple juice; the mixture may look slightly curdled, which is fine.
- In a large bowl, beat the 1/2 cup softened butter and the 3/4 cup granulated sugar with an electric mixer on medium speed until pale and fluffy, about 3 minutes.
- Beat in the eggs one at a time, then the vanilla.
- On low speed, add the flour mixture in three parts, alternating with the milk and juice mixture in two parts, beginning and ending with flour. Mix only until the batter is smooth.
- Spoon the batter over the fruit in dollops and spread it gently to the edge of the skillet without disturbing the pineapple.
- Bake for 40 to 45 minutes, until the cake is golden brown, springs back when pressed in the center and a toothpick inserted into the cake layer comes out clean.
- Set the skillet on a wire rack and let it stand for 10 minutes, no longer. Run a thin knife around the edge of the cake.
- Place a flat serving plate, larger than the skillet, upside down over the pan. Wearing oven mitts and holding the plate and skillet firmly together, flip them over in one motion. Leave the skillet in place for a minute so the caramel can run down, then lift it off. Put back any fruit that sticks to the pan.
- Serve warm or at room temperature.


