Posted by: A Part of the Solution | May 17, 2012

Cast Iron Pineapple Upside Down Cake

Don’t you just love a good pineapple upside down cake? Not so much? They’re too sugary, right? And those pineapple upside down cakes were mooshy on top and in the middle, am I wrong? I hear you. But they always look like they’re going to be just so good.

As it happens, I have the solution to the conundrum of the desirable pineapple upside down cake. That recipe, the one which doesn’t use a box mix or a can of tinny tasting pineapple chunks exists. Dry your eyes, now. I appreciate those tears of relief and gratitude, but you’ll want to read carefully and follow the directions exactly.

Cast Iron Pineapple Upside Down Cake

For the Pineapple Upside Down:

4 TBSP, 1/2 stick or 2 oz, softened butter (out a room temperature for a while, or in the microwave at half power for a ten second interval)

3/4 cup, 5.25 oz, brown sugar

4 cups, 1 1/2 lbs, fresh pineapple in half inch pieces

For the Cake:

1 1/2 cups, 7.5 oz, all purpose unbleached flour

2 tsp baking powder

1/2 tsp salt

8 TBSP, 1 stick or 4 oz, softened butter (see note above)

3/4 cup, 5.25 oz, granulated sugar–if you’ve got vanilla sugar now would be a good time to use it

2 large eggs at room temperature

1 large egg white at room temperature

1 tsp vanilla extract

1/3 cup, 2.67 oz, whole milk at room temperature

Set your oven rack for the middle position. Preheat the oven to 350°. Place the 2 0z portion of butter in a cast iron pan measuring  9″ across the bottom and set the pan in the oven until the butter is completely melted (about 6-8 minutes). Stir the brown sugar into the melted butter and spread the mixture evenly across the pan’s bottom. Now press the pineapple pieces into the sugar-and-butter mixture. Make them as level as possible. Set the pan aside.

In a small mixing bowl, stir together the flour, baking powder and salt with a fork until well combined. In a large mixing bowl, cream the 4 oz portion of butter with the granulated sugar. Beat this, by hand using a wooden spoon or with a mixer, until the butter and sugar are light colored and very thick and about twice the volume they started. Add the eggs one at a time and beat well in before adding the next. Beat in the egg white the same way. Now add the vanilla extract and incorporate fully.

Add one third of the flour mixture to the big mixing bowl and slowly beat the dry ingredients into the creamed mixture. Now add half the milk and beat until the batter is just smooth. Add another third of the flour, as before. Add the rest of the milk to the mixing bowl. And lastly, beating only until just combined, add the rest of the dry ingredients.

Spoon the batter gently onto the pineapple. Smooth the thick batter carefully with a spatula. Bake the pineapple upside down cake for 45 minutes. It will be quite brown on top, and a toothpick inserted in the middle will come out clean. Take the pan from the oven and let it sit for 10 minutes undisturbed. Invert a large plate over the cake. Using pot holders, invert the pan and the plate. Let the pan sit on the plate for a full minute. Give it a hefty thump (again using a pot holder to protect your hand), and lift the cast iron pan straight up–and not too quickly.

Push any stray pieces of pineapple back onto the top of the cake. Let it cool for 20-30 minutes before serving. Oh gosh!



  1. Sounds like a fun project! I read somewhere you can substitute 3 tbsp molasses + 1 cup sugar (ratio) for brown sugar. Does that work here? I know you said “follow directions exactly” but wasn’t sure if that applied to substitutes 🙂

    • Yvette, you’ll want 1 TBSP molasses + 1 cup granulated sugar (- 1 TBSP sugar), or 15 TBSP–but really it’s easier to subtract one than it is to add fifteen, so do it the easy way. That will give you the lighter brown sugar you’re looking for. If you want dark brown sugar, add 2 TBSP molasses and subtract 2 TBSP sugar to get the right proportions. Happy baking!

  2. Mmmm…yummy!! definitely gonna try this one! Pineapple Upside Down Cake was my dad’s favorite, so i had lots of mushy insides when i was growing up…but that’s another topic altogether!

    • I hear it. That’s why this one really does shine. It just isn’t damp in the middle. And I had some the next day, 24 hours after baking–still structured. Still not mooshy! This is very much worth making.

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