Pineapple Upside Cake

We have been doing some intense cooking the last couple of weeks of school. In my quest of encouraging my students to use fresh ingredients and making items from scratch. I  bought fresh pineapples for them to make pineapple upside down cake. Most of my students  have never cut into a fresh pineapple. I was a little nervous watching them cut them up and cutting out the cores. The students were using the big chef knives to cut the pineapples apart. I think I only had to hand out one band aide.  Relief. Not to brag (but I am) my class made beautiful double layered upside down cakes. Yes, you read right. Double Layers! I let them find a recipe they all agreed upon. They chose a double layered and iced pineapple upside-down cake from Paula Deen. The cake was such a hit and so many teachers wanted to try a bite, that I went and bought another fresh pineapple and made one for them.

You will need a pineapple, flour, sugar, brown sugar, powdered sugar, butter milk, eggs, maraschino cherries, baking powder, vanilla and salt. (I forgot to include salt in the picture) oops.


The first thing you do is cream two sticks of softened butter with a mixer.


Add in the granulated sugar and cream together.


Now it is time to add the eggs one at a time to the creamed sugar and butter mixture.


When all the eggs are added in the mixture turns very cream. Now, you can add in the vanilla and mix.


In a separate mixing bowl, mix together the flour, salt and baking soda. This is also the time to measure out the butter milk.


Alternately add a little bit of the flour mixture and combine. Then add in a little bit of the buttermilk and combine.


Continue to alternate adding the flour and buttermilk, until all the flour and buttermilk is used.


Next, I cut up the fresh pineapple. I first cut off the top and then then started cutting the outer part of the pineapple off.


I sliced the pineapple into 1/2 in slices. I took a small biscuit cutter and cut out the cores of the pineapple slices.


When you pick out the round pans to make this cake, pick the taller pans as the cake rises up and the brown sugar cannot bubble out.  I prepared both pans with a spray of vegetable spray and lining the bottom of each pan with parchment paper.


I put equal amounts of brown sugar in the bottom of each pan. Spread the brown sugar evenly on the bottom of each pan.


Pour equal amounts of melted butter on the brown sugar in each pan.


Now, you can get a little creative and decorate the bottom (which will be the top) of each cake with pineapple and maraschino cherries. Equally fill both pans with cake batter.


Bake in the oven until the cake is done. Cool the cake on a cooling rack until the cakes are completely cool. (I refrigerated mine for a time to make the cake easier to ice)


You make the icing by creaming the butter with a mixer. (You use two sticks of butter, I just took my picture before I put the other stick of butter in the mixing bowl)


Add in the vanilla. Add in enough water to make a spreadable icing. You could also use pineapple juice or the maraschino cherry juice (it will turn pink) instead if you want.


Here is a picture of the finished icing. Now, gently stack the cakes on top of each other.


Very gently, ice the sides of the cake. This cake is really tender and moist, which is a great thing, but you have to be careful of crumbs coming off in the icing.

Isn’t this slice of cake a beautiful thang…thing?

I refrigerated the cake overnight, before I cut it into slices. It sliced beautifully this way.

If you are looking for a show stopper kind of cake or want to try making this cake with fresh pineapple…it really does make a difference….give this cake a try.

Here is the recipe:

Adapted from Paula Deen

Ingredients for the cake:

3 cups of cake flour (I used all purpose flour)

1 cup butter soften PLUS 1/2 cup butter melted

2 1/4 cups sugar

5 large eggs

1 tablespoon vanilla extract

2 teaspoons baking soda

1/4 teaspoon salt

1 1/4 cups buttermilk

1 1/2 cup firmly packed brown sugar

1 fresh pineapple, sliced, peeled and cored (if you do not want to use fresh pineapple use 2 – 20 ounces cans of sliced pineapple)

1 – 10 ounce jar of maraschino cherries

Ingredients for the buttercream frosting:

1 cup butter softened

2 tablespoons of water or you can use pineapple juice or maraschino cherry juice

3 1/2 cups of powdered sugar

1 teaspoon vanilla

Directions for the cake:

Preheat the oven to  350 degrees. Spray two 9 inch round cake pans with vegetable spray and line the bottoms with parchment paper.

In a large mixing bowl, cream the butter with an electric mixer. Add in the sugar and mix until fluffy.. Add in the eggs, one at a time. Beating well after each egg. Stir in the vanilla. Set aside.

In a medium mixing bowl, stir together the flour, baking powder and salt.

Alternately mix in the flour mixture and the buttermilk into the egg mixture.

Press 3/4 of a cup of brown sugar onto the bottom of each round cake pan. Pour the 1/2 cup of melted butter equally onto the brown sugar in each pan. Arrange the pineapples and cherries over the brown sugar.

Top the pineapples with equal amounts of cake batter.

Bake for about 40 minutes or until tooth pick comes out clean.

Let the cakes cool for 10 minutes, then invert onto a cooling rack. Remove the parchment paper. Cool completely.


In a mixing bowl, beat all the icing ingredients together until fluffy.

To assemble the cake:

Carefully stack one cake onto of the other cake. Ice the cake with the buttercream frosting.

You can press chopped pecans into the icing for a garnish if desired.

I hope you love this cake enough to jump upside down ; )



Other cake post you make enjoy:


Peanut Butter Mousse Cake              Best Ever Chocolate Cake           Blueberry and Blackberry Oat Cake