Brown Sugar Crumble Pineapple Upside Down Cake

Originally published on “Blaise the Baker” April 21st, 2015

Yesterday was “National Pineapple Upside Down Cake”, and of course I had to make one – and if you ask me…it was fabulous! I make mine a little different than most, by adding extra butter and brown sugar (color you surprised, right!?) – but it really makes a difference! It adds almost like a “brown sugar crumble” on top of the cake that is super sweet and really adds to the cake, and forms a delicious crust around the edges of the cake. You really must try it…

Yes, I have made these from scratch – no, I did not yesterday. I used a cake mix because honestly, it is the cake mix version of this recipe that I remember from childhood, and I needed a trip down memory lane yesterday. If you want to use this recipe with your homemade pineapple cake recipe, please feel free. It will work out either way.


Brown Sugar Crumble Pineapple Upside Down Cake

1 box of “Duncan Hines” pineapple supreme cake mix and the ingredients to go along with it (eggs and oil)
1 can of sliced pineapple rings in their own juice (20 oz.)
Small jar of maraschino cherries (without their stems)
1 stick of salted butter (4 oz.)
2 cups light brown sugar, lightly packed

Start by preheating the oven to 350 degrees-F. Place the stick of butter in a 13×9-inch cake pan and place it into the oven, to melt, while the oven is preheating.

Open the can of sliced pineapple rings, and drain the juice into a measuring cup. Fill the rest of the measuring cup with water until it reaches the “1 cup” mark and set aside.

In a large bowl, whisk together the cake mix, eggs, oil and pineapple juice/water until there are no more lumps in the batter, and it’s smooth and pale in color.

Carefully remove the 13×9-inch cake pan from the oven. If the butter is completely melted (if not – place back in oven for a couple of minutes), sprinkle the brown sugar all over the top of the melted butter, evenly.

Place the pineapple slices on top of the brown sugar. I place mine from left to right – 3 slices, 2 slices, 2 slices, and then 3 slices – 10 slices total.

Next, place single maraschino cherries in the hole of each pineapple slice. I also place a few of the cherries around the pan – just for extra – it’s really up to you.

Pour the cake batter, evenly, over the pineapple slices, cherries and brown sugar.

Place into preheated oven for exactly 44 minutes.

Once the cake is baked, remove from oven and allow to sit only 5 minutes before running a knife around the edges of the pan, and flipping it upside down on a piece of parchment paper. Be careful of this step – the pan is hot. If anything “sticks” to the inside of the pan, remove with fork or knife, and place back on the cake.

Allow to cool slightly before serving.

Store any leftovers in an airtight container in the refrigerator.



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