Double Layer Pineapple Upside Down Cake

Double Layer Pineapple Upside Down Cake

Believe it or not, this is one gorgeous cake.

Unfortunately, the photos don’t reflect how beautiful it is. It can be hard to be a foodblogger in the Winter. I’ll let you in on a secret. I take my best photos in the daylight…usually on my porch. I have a special food photography light, but I don’t feel like I get the same kind of result. So as the day goes on, I feel like I’m racing the sunset.

I made this cake for a friend by special request, but it was evening before I could shoot it. In my opinion, the photos don’t do it justice. In person, this cake looks like a party! The pineapple and cherries glisten like colorful jewels. The white pineapple frosting and toasted pecans that surround the cake bring a beautiful textural and visual contrast.

This is a dessert with tons of TA DA!

Double Layer Pineapple Upside Down Cake
Adapted from a recipe by Paula Deen.

  • 3 cups cake flour, plus more for pan
  • 1 cup butter, softened, plus 1/2 cup, melted
  • 2 1/4 cups sugar
  • 5 large eggs
  • 1 teaspoon vanilla extract
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1 1/4 cups whole buttermilk
  • 1 1/2 cups firmly packed brown sugar
  • 2 (20-ounce) cans pineapple slices in juice, drained well (reserve 2 tablespoons juice for frosting)
  • 1 (10-ounce) jar maraschino cherries, drained well
  • Pineapple Buttercream Frosting, recipe follows
  • Chopped pecans, for garnish, optional


  • 8 ounces cream cheese
  • 4 ounces unsalted butter, room temp
  • 1 tablespoon pineapple juice from the can
  • 2 1/2 to 3 cups powdered sugar
  • Chopped toasted pecans, for garnish, optional

Preheat the oven to 350 degrees F. Spray 2 (9-inch) round cake pans with nonstick cooking spray.

In a large bowl, beat 1 cup butter at medium speed with an electric mixer until creamy. Gradually add the sugar, beating until fluffy. Add the eggs, 1 at a time, beating well after each addition. Stir in the vanilla and set aside.

In a small bowl, add the 3 cups of flour, baking powder, and salt. Stir to combine. Add the flour mixture into the egg mixture alternately with the buttermilk, beginning and ending with the flour mixture.

Divide the brown sugar evenly into each pan. Pour the melted butter equally over the brown sugar. Arrange the pineapple slices and cherries over the brown sugar. Isn’t that pretty?

You will have pineapple and cherries left over. Pour equal amounts of batter over the fruit and bake until a wooden pick inserted in center comes out clean, about 40 to 45 minutes.

Let the cakes cool in the pans for 10 minutes. Invert the cakes onto wire racks to cool completely.

To assemble the cake, carefully arrange 1 cake layer, pineapple side up, on a cake plate.

Then, I recomend that you pipe a ring of frosting around the outer top edge of the cake. The reason for this is that the cake isn’t flat on top and when you stack the second later, it will want to bend creating little cracks on the surface of the top layer of cake. The ring of frosting flattens the top of the bottom layer to receive the top later. I hope this makes sense because I failed to take a picture.

Carefully stack the remaining cake layer, pineapple side up, over the first layer (with the frosting piped around the edge). Frost the sides of the cake with Pineapple Buttercream Frosting. Press chopped pecans into sides of cake.

Slice and eat.