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Pineapple Upside Down Cake Day

Pineapple Upside Down Cake

Apparently this is the “most amazing thing” I have ever made.  So, I just had to share it here because it is National Pineapple Upside Down Cake Day!  

With that being said, you should all run right out and make these asap.  I was really unsure about how these guys would go over.  I mean, there is an avid group out there that does not like desserts without chocolate.  I had to make a dessert for 30ish people (thus the use of the GIANT mixer) for a “luau” themed party.  I decided on Pineapple Upside Down Cupcakes, but I was nervous about how people would like them.

Pineapple Upside Down Cake



Not only did they turn out FANTASTIC, but I had enough extra cake batter to make a bundt cake and people were obsessed with them.  The cupcakes were amazing, and the cake was delicious with some fruit or whipped cream on top.  The desserts fit perfectly with the theme and were an overall huge success! In fact, they went so fast, that I didn’t really have time to take any pictures! I apologize for the poor lighting here, but please take my word for it, they are amazing.



Pineapple Upside Down Cupcakes (adapted from The Comfort of Cooking)


Pineapple Upside Down Cake
Before flip…
Pineapple Upside Down Cake
After flip! 


36 pineapple slices

18 tbsp unsalted butter

3 cups packed brown sugar

6 tbsp light corn syrup

9 eggs

6 cups sugar

3 cups canola oil

3 cups (24 oz) sour cream

6 tsp vanilla

7 1/2 cups flour

1 1/2 tsp baking powder

1 1/2 tsp baking soda

1 1/2 tsp salt





1. Grease enough cupcake pans to make 36 cupcakes. Preheat oven to 350 degrees.

2. In a large saucepan over medium heat, melt the butter and stir in the brown sugar and corn syrup. Scoop 1 tbsp of this mixture into the bottoms of each cupcake well. Place 1 pineapple slice in each well.

3. In a large bowl (or giant stand mixer) beat the eggs and sugar until light and fluffy.  Beat in the oil, sour cream, and vanilla until well combined.  Mix in the flour, baking soda, baking powder, and salt.  Beat until just combined.

4. Fill each cupcake well to the top with batter.  Bake for 25-28 minutes.  Let cool for 5 minutes before flipping.

Enjoy 🙂

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Just a college girl learning how to be the best math teacher ever, and cooking and baking my way through life.

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