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Pineapple Upside-down Cake

From smittenkitchen.com, adapted from Gourmet.

Difficulty rating: 5 out of 10 (For the caramel only because of the potential burning factor. And, I suppose, if you actually peeled and cored a whole pineapple. The cake itself is simple.)


  • 1/2 medium pineapple, peeled, cored and quartered lengthwise
  • 3/4 stick unsalted butter
  • 3/4 C. light brown sugar


  • 1 1/2 C. all-purpose flour
  • 2 tsp. baking powder
  • 1/4 tsp. salt
  • 3/4 stick unsalted butter, softened
  • 1 C. granulated sugar
  • 2 large eggs
  • 1 tsp. vanilla
  • 1 Tbsp. dark rum
  • 1/2 C. unsweetened pineapple juice
  • 1 to 2 Tbsp. dark rum to sprinkle over cake

Special equipment: 10-inch cast iron skillet, seasoned. (If you don’t have one of these, you can make the caramel in a small saucepan and then pour into a 9-inch cake pan to bake instead.)

Preheat oven to 350°F.

Making topping:
Cut pineapple crosswise into 3/8-inch-thick pieces.

Melt butter in skillet. Add brown sugar and simmer over medium-low heat, stirring, for four minutes. (Adjust heat level to your stovetop, but err on the low side. You can always cook it longer or turn up the heat, but you can’t un-burn it!) Remove from heat.

Arrange pineapple on top of sugar mixture in concentric circles, overlapping pieces slightly, from the middle to the edge of the skillet/pan. (See above photo for an example.)

Making batter:
Sift flour, baking powder and salt into small bowl.

Beat butter in a large bowl with an electric mixer until light and fluffy, then gradually beat in granulated sugar. Add eggs, one at a time, beating well after each addition. Beat in vanilla and rum.

Add half of flour mixture and beat on low speed just until blended. Beat in pineapple juice, then add remaining flour mixture, beating just until blended.

Spoon batter over pineapple topping and spread evenly. Bake cake in middle of oven until golden and a tester comes out clean, about 45 minutes.

Let cake stand in skillet five minutes, then lay a plate over skillet and invert cake onto plate. (I inverted mine directly onto my cake stand.) Replace any pineapple that may have stuck to the bottom of skillet. Sprinkle rum over cake and cool on plate on a rack.

(We stopped at 1 Tbsp. of rum because it already smelled pretty strongly of rum at this point for one thing and also, Katie & Patrick don’t drink, so we didn’t want to douse the cake too heavily. It was perfectly delicious this way.) 

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