I’ve tried quite a few Upside Down Pineapple Cake recipes. This recipe, courtesy of Simply Recipes, is hands down the best. The cake itself is heaven and the topping is rich and delicious. It is divine when served with whipped cream.
A few notes: There is an option of using either all purpose flour or using a mix of all purpose / cake flour / ground almond. I have always used just the regular all purpose flour and the cake turns out incredible.
In the original recipe, the brown sugar mixture for the topping is prepared on the stove and brought up in heat until it is bubbling. I usually just melt the butter and brown sugar, stir well, and call it good, either in the microwave or on the stove top. I just note this now if you were wondering if you could save a few minutes to skip that step. I do and it turns out great anyways.
The rest of my notes are regarding to how I prepare the cake.The original recipe uses a 2 inch deep cake dish. I prefer a thinner cake so I split the batter in two and use two slightly smaller cake plates (1 1/2 inch deep plates). Since I split the cake in two, I double the topping and divide it between the two plates.
My cook time is less than the original recipe because my cakes are thinner. If you prefer to only make one large, extra deep cake, please follow the original recipe at Simply recipes.
Overall I just like making two cakes instead of one because I feel like the cake to topping ratio is perfect that way, and you also have one cake to keep for yourself and one to give away to a friend. Enjoy!
The Best Pineapple Upside Down Pineapple Cake
Makes two 9″ cakes.
Note: I used 1 1/2″ tall cake pans, which makes two cakes. If you use a 2″ tall cake pan you should be able to fit all the batter into one dish, but it will take longer to bake, about 1 hour and 15 minutes.
- For the topping (for 2 cakes)
- 2 cups brown sugar
- 1 cup butter
- 14 sliced pineapple rings (which is 1 1/2 20 oz. cans)
- 14 maraschino cherries
- For the cake:
- 2 cups flour (Or 1 1/2 cups flour + 6 Tbsp. cake flour + 6 Tbsp. ground almond)
- 3/4 tsp. baking powder
- 1/2 tsp. salt
- 1 3/4 cup sugar
- 1 cup butter
- 4 large eggs
- 3/4 tsp. vanilla
- 3/4 cup sour cream
- Prepare the topping: Melt the butter and brown sugar in a sauce pan over medium heat and stir until completely dissolved. Place the pineapple rings into the two prepared 9″ cake pans. Add a cherry inside of each pineapple ring. Divide the topping mixture in two. Pour topping over pineapple slices.
- Prepare the cake: Preheat oven to 325 degrees F. Whisk the flour, baking powder, and salt in a large mixing bowl. In a separate bowl, use an electric mixer to beat the sugar and butter together until light. Add eggs one at a time, beating after each addition. Beat in the vanilla. Add dry ingredients alternately with sour cream in 2 additions each, beating well after each addition. Divide batter in half. Pour cake batter over caramel and pineapple in pans.
- Bake cake until tester inserted into the center comes out clean, about 35-40 minutes. (See notes above if you used a 2″ cake pan – It will take longer to bake if so). Cool cake in pan on a rack for 10 minutes. Turn cake out onto a platter. Serve warm or at room temperature.