Pineapple Upside-Down Cake

  • Level: Easy
  • Yield: 8 servings
  • Total: 1 hr 10 min
  • Active: 20 min
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Ingredients

2 1/2 cups all-purpose flour

2 cups granulated sugar 

1 1/2 cups whole milk 

1/4 cup vegetable shortening 

1 tablespoon baking powder 

2 teaspoons vanilla extract 

1 teaspoon kosher salt 

2 large eggs 

One 20-ounce can sliced pineapple plus 2 tablespoons juice

1 stick (8 tablespoons) unsalted butter, at room temperature 

1 1/3 cups packed light brown sugar 

Maraschino cherries, as needed, stemmed

Directions

  1. Preheat the oven to 350 degrees F.
  2. Make the cake batter: Combine the flour, granulated sugar, milk, shortening, baking powder, vanilla, salt, eggs, pineapple juice and 4 tablespoons of the butter in a large bowl. Beat with a mixer on medium speed until well combined. (There will still be a few small lumps in the batter.) Set aside.
  3. Melt the remaining 4 tablespoons butter in a 12-inch cast-iron skillet over medium heat; swirl to thoroughly coat the skillet. Sprinkle the brown sugar over the butter, making sure it's evenly distributed--you want the entire surface of the butter to be covered in brown sugar. Do not stir. As soon as the sugar dissolves, remove from the heat, layer the pineapple slices over the top and add cherries to the middle of the pineapple slices. Pour the batter evenly over the pineapple and gently spread to even out the top. Bake until a toothpick inserted into the center of the cake comes out clean, 30 to 40 minutes.
  4. Immediately run a knife around the edge of the cake, then put a plate upside down on top of the skillet. Carefully invert the skillet so the cake is turned onto the plate. It should come out pretty easily; if bits of cake stick to the skillet, use a small knife to patch it together. Let cool slightly before cutting into wedges. It's best served warm, but room temperature is fine too.

Let's Get Cooking!

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Anonymous

There are some pretty big flaws with this recipe. 4 stars because I made tweaks to override those flaws. First of all, if you want a light, fluffy cake you better cream the fats and sugar, and then beat more after each egg. A lot more. I decreased the 2 cups of sugar in the cake to 1.5 cups, and it was still very sweet. Doubled the vanilla to give some good flavor to an otherwise bland cake. The amount of brown sugar is also crazy…I used 3/4 c. And it was still a very generous amount. And the baking time in the recipe? Follow it and you’ll get an uncooked cake. Instead of 40-50 min. mine baked for 70 min.

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