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Pineapple upside-down cake with seven pineapple rings and cherries beside a cast iron skillet

Cast Iron Skillet Pineapple Upside-Down Cake

A vanilla butter cake baked over pineapple rings, cherries and a butter and brown sugar caramel in a 10-inch cast iron skillet, then turned out upside down.
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Prep Time 20 minutes
Cook Time 45 minutes
Cooling time 10 minutes
Total Time 1 hour 15 minutes
Servings: 8 slices
Course: Dessert
Cuisine: American
Ingredients Method Notes

Ingredients
  

Topping
  • 4 tablespoons (1/2 stick) unsalted butter
  • 2/3 cup packed light brown sugar
  • 1 can (20 ounces) pineapple slices in juice, drained, 1/4 cup of the juice reserved
  • 7 maraschino cherries stemmed and drained (optional)
Cake
  • 1 1/2 cups (180 g) all-purpose flour, spooned and leveled
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon fine sea salt
  • 1/2 cup (1 stick) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 2 large eggs at room temperature
  • 1 teaspoon vanilla extract
  • 1/4 cup milk at room temperature
  • 1/4 cup reserved pineapple juice from the can

Method
 

Prepare the skillet
  1. 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.
  2. 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.
  3. Sprinkle the 2/3 cup brown sugar evenly over the melted butter. Do not stir.
  4. 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.
Make the batter
  1. 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.
  2. 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.
  3. Beat in the eggs one at a time, then the vanilla.
  4. 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.
  5. Spoon the batter over the fruit in dollops and spread it gently to the edge of the skillet without disturbing the pineapple.
Bake and turn out
  1. 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.
  2. 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.
  3. 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.
  4. Serve warm or at room temperature.

Notes

The skillet and its handle stay very hot for a long time after baking. Keep a mitt or towel over the handle as a reminder, and get help with the flip if the pan is heavy.
Do not let the cake cool completely or store it in the skillet. The caramel sets and glues the fruit to the pan, and the acidic pineapple can pick up a metallic taste from the iron and wear away the pan's seasoning. If the cake has cooled too long, warm the skillet over low heat for 1 to 2 minutes to loosen the caramel before inverting.
A 20-ounce can holds about 10 slices; 7 fit in a 10-inch skillet. Halved slices can be stood around the side of the pan if desired. For a 12-inch skillet the cake will be thinner; start checking it at 30 minutes.
Fresh pineapple works as well: cut peeled, cored slices 1/2 inch thick, and replace the pineapple juice in the batter with the same amount of milk.
Cover leftover cake and keep it at room temperature for up to 2 days or in the refrigerator for up to 4 days. Rewarm slices briefly before serving.