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Over-the-top Pineapple Upside-down Cake

Updated: Jan 15, 2019

This is an amalgamation of 3 different recipes to create a more interesting version of the classic pineapple upside-down cake. The cake itself is rich and spicy (lots of brown sugar, butter and cinnamon here!) In between the layers is a boozy adaptation of Magnolia Bakery's coconut filling, with some walnuts added for texture. Topped off with a sunburst design of pineapple slices, this traditional cake is brought to a whole 'nother level!




1/4 C. butter

1-2 tsp. brandy

1/2 C. packed brown sugar

6 pineapple rings

11 maraschino cherries

11 walnut halves

Coconut Walnut filling - adapted from Magnolia Bakery

3/4 C. milk

1/2 C. granulated sugar

2 Tbsp. all-purpose flour

4 oz. sweetened shredded coconut

3 oz. chopped walnuts

1 teaspoon vanilla extract

1 Tbsp. brandy

Brown Butter Spice Cake

2 sticks of butter (unsalted or salted is fine), browned and cooled

2 C. brown sugar

4 eggs

1 Tbsp. + 1 tsp. vanilla

1/2 tsp. coconut extract

3 C. all-purpose flour

1 tsp. baking soda

1 tsp. baking powder

1 heaping Tbsp. cinnamon

1 1/2 tsp. ground ginger

1 1/2 tsp. nutmeg

1 1/2 C. crushed pineapple


For the cake

1. Grease two 8" cake pans with butter. Cut out a circle of parchment paper to line the bottom of one pan. (This will make the cake easier to turn out.)

2. In the other cake pan (the upside-down layer), arrange the topping ingredients. Pour in the melted butter and brandy, sprinkle evenly with brown sugar, and then create the fruit and nut design. I went for a sunburst pattern as pictured, but feel free to change it up. You're the artist! :)

3. Combine butter, brown sugar, eggs and vanilla. Slowly increase mixer speed to medium-high, until ingredients are creamed together.

4. In another bowl, thoroughly mix together the flour, baking soda and powder, and spices.

5. Add dry ingredients to the butter mixture, little by little. Mix until just incorporated.

Note: At this point, the batter may seem very heavy and almost dough-like. Not to worry! This will be remedied in the next step...

6. Gently fold in crushed pineapple. The fruit juices will help to thin down the cake batter, so it becomes easier to spread.

7. Divide the batter (almost) evenly between the cake pans and smooth to the edges with a spatula. I skimped on batter for the upside-down layer because the fruit of course takes up some space.

8. Bake at 350⁰F for 50-60 minutes. The upside-down layer will take longer due to all the moisture from the fruit. I had great success with baking this on our grill (don't want to heat up the house with the oven.) If you choose to bake on the grill too, just be cautious of hot spots.

9. Turn out the upside-down layer immediately onto a pan and allow to sit, so the caramel begins to soak into the cake. The other layer should cool approximately 15-20 minutes before turning out.

For the filling

1. Combine milk, sugar, and flour in a saucepan on medium heat. Stir constantly until mixture has thickened, approximately 5 minutes.

2. Remove from heat and quickly whisk in coconut, walnuts, extract and brandy. Feel free to add more brandy, so long as it doesn't become runny. We want to maintain a frosting texture that will hold the cake layers together.


I'm going to be very honest here and say that assembling this cake is not easy. You have my permission to laugh when I tell you that the upside-down layer kind of fell apart... chunks of fruit all over the counter. I simply pieced it back together. The moist, caramel-y texture of this layer actually make it quite easy to reassemble if need be.

Remember, you are all alone in the kitchen, and no one can see you. ~Julia Child

I was working on this by myself, but if you can employ someone's help to stack the cake layers, I would encourage you to do so. Extra hands (and spatulas) can be invaluable in a precarious task like this.

1. Center the plain cake layer on a decorative plate or stand.

2. Spread all of the coconut filling evenly across the top.

3. Using a large spatula, carefully ease the upside-down layer from the pan onto the frosted layer. If you have one of those handy-dandy round cake lifter spatulas, now is the time to use it. I don't have one yet, but it's certainly on my wishlist!

4. Breath a very large sigh of relief. :)

It's a great deal of work, but I believe this cake is worth it. Served warm with a scoop of ice cream, it is simply marvelous!

'Til next time,



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