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Writer's pictureJoyce

Dreamy-Good Pineapple Upside-Down Pound Cake

Updated: Feb 29, 2020

I've made a lot of cakes in my life, but I made my first pineapple upside down cake this month. When looking for a recipe I could use as a starting point, I ruled out all the versions using cake mixes and pudding mixes because avoiding excessive preservatives and ingredients I can't pronounce is important to me.


Real cakes are made with fat (oil/butter), sugar, eggs, and vanilla... and then they alternate between adding a flour mixture and adding milk/buttermilk. This process allows a made-from-scratch cake to absorb the ingredients properly. When I found that kind of recipe, I started to tweak it and make it my own. I adjusted the ingredients to fit my needs and then I pureéd some pineapple and juice to replace the milk concept and to add more pineapple flavor and more moisture.


The end result is a fantastic pineapple-flavored pound cake that might even taste better the second day. Here's the recipe:


Ingredients for a Party-Size Cake:


In the pan:

1 stick unsalted butter

1 1/2 cups brown sugar

One 20-ounce can sliced pineapple (set aside the leftover slice and juice in case you need to use them in the pureé below)

9 pitted cherries or maraschino cherries (preferrably homemade maraschino cherries)


In the mixer:

2/3 cup unsalted butter, softened

1 cup minus 1 Tbsp sugar

4 eggs

2 tsp pure vanilla

3 1/2 cups flour, spooned and leveled (use 3 1/3 cups flour for lower elevations)

5 tsp baking powder

1/2 tsp salt

3 cups pineapple pureé (roughly one 20-ounce can of pineapple (slices/chunks/tidbits) pureéd in a blender)


Instructions:


1. Using a fork, gently remove 9 pineapple slices from the can and put them in a colander with the 9 cherries. (You won't need the juice that drains off of the pineapple and cherries.)


2. In a full-size cast iron skillet, melt the butter and spread it up the sides of the pan. Mix in the brown sugar, and spread the mixture evenly along the bottom of the pan. Turn off the heat. (If you don't have a cast iron skillet, melt the butter, mix in the brown sugar, and spread it on the bottom of a deep 9X13 pan.)


3. Preheat the oven to 375 degrees (Fahrenheit).


4. Arrange nine pineapple slices in a ring around the pan. Put one slice in the middle. Add the cherries to the center of each pineapple ring. You can try other patterns and other forms of pineapple (like chunks or tidbits), but this pattern is the most consistently recognizable after it has been baked.


5. In the mixer, blend the butter and sugar until smooth. I rarely measure butter this way, but for cakes, I do if the butter is still somewhat firm because then I know it has been softened enough and that there are no cold spots.


6. Add the eggs and vanilla, blend until smooth and scrape the bowl and the beaters and blend it again.


7. In a separate bowl (this does matter), mix the flour, baking powder, and salt.


8. Add about 1/3 of this dry mixture to the mixing bowl and mix just until it's combined.


9. Pour 1/2 of the pineapple mixture in to the mixing bowl and mix just until it's combined.


10. Add another 1/3 of the dry mixture to the mixing bowl and mix just until it's combined.


11. Pour the remaining pineapple mixture into the mixing bowl and mix just until it's combined.


12. Add the remaining flour mixture, mix it in, and scrape down the bowl and the beaters and blend it again. The resulting batter should be somewhat similar to pancake batter.


13. Pour this mixture into the cast iron skillet (or the 9X13 pan) and bake at 375 degrees for about 45 minutes. The top should be golden brown. When you insert a toothpick to test if it's cooked, you'll need to wiggle the insertion hole a little wider - otherwise the tiny opening will scrape off any evidence from the toothpick and you will have a hard time knowing if it's really cooked.


Please note: Almost EVERYONE says that you should bake a cake until a toothpick comes out clean (with no cake batter on it). To me, this is a LIE. It's only true if you enjoy dry cake, but virtually no one does! If you want a moist cake, you should bake it until the toothpick comes out with CRUMBS on it.


These are your options:

A. The toothpick is wet with batter - bake it for another 1-2 minutes if it has a LITTLE BIT of wet batter or another 5 minutes if it has A LOT of goopy batter on it, then check it again in a new spot after the timer goes off again.

B: The toothpick has crumbs stuck to it - THIS IS CAKE PERFECTION. Remove it from the oven IMMEDIATELY and then quickly do a little happy dance!

C: The toothpick is dry - this cake is overdone. Go buy some ice cream and serve it with the cake so hopefully no one will notice.



14. Let it cool for 12-14 minutes (but not longer!). If you wait longer than 14 minutes, you will have a very hard time getting it out of the pan. If you try flipping it sooner than 12 minutes, you risk having the whole thing fall apart.


15. Run a sharp knife gently around the edge of the pan (between the cake and the pan) to make sure none of the sides of the cake are stuck to the pan.


16. Invert a cooling rack on top of the cake, then grip both the cake and cooling rack and flip it over. Remove the pan and let the cake cool for 30-40 minutes while you clean up the kitchen.



Please note: I left the maraschino cherries in this recipe because my husband truly enjoys them - I scoop the little red demon out of my slice and discard it. If you're looking for a healthier option, please remove them. Don't let this alleged fruit fool you; I promise that there is literally nothing in a commercially-produced maraschino cherry that is good for your health. (Bottling and using your own maraschino cherries decreases the health risks significantly).


Another note: My husband swears that this cake is better when it's cold, but truthfully, he prefers EVERY cake he eats to be cold, so I'll let you be the judge of that.


Final note: If you want a more family-size cake, just cut all the ingredients in half and bake it in a smaller cast iron skillet (or in a deep 8X8 pan). I made sure this recipe was super-easy to make in a smaller size because the recipe above really is meant to be served at a party.


If you make this in a 9X13 or 8X8 pan, please let me know about your experience in the comments below. I use two sizes of cast iron skillets (one for party-size and one for family-size), so I haven't had to resort to using any other pans yet.


RECIPE SUMMARY


Ingredients for a Party-Size Cake


In the pan:

1 stick unsalted butter

1 1/2 cups brown sugar

One 20-ounce can sliced pineapple

9 pitted cherries


In the mixer:

2/3 cup unsalted butter, softened

1 cup minus 1 Tbsp sugar

4 eggs

2 tsp pure vanilla

3 1/2 cups flour, spooned and leveled (use 3 1/3 cups flour for lower elevations)

5 tsp baking powder

1/2 tsp salt

3 cups pineapple pureé


Instructions:


1. Using a fork, gently remove 9 pineapple slices from the can and put them in a colander with the 9 cherries.


2. In a full-size cast iron skillet, melt the butter and spread it up the sides of the pan. Mix in the brown sugar, and spread the mixture evenly along the bottom of the pan. Turn off the heat.


3. Preheat the oven to 375 degrees (Fahrenheit).


4. Arrange nine pineapple slices in a ring around the pan. Put one slice in the middle. Add the cherries to the center of each pineapple ring.


5. In the mixer, blend the butter and sugar until smooth.


6. Add the eggs and vanilla, blend until smooth and scrape the bowl and the beaters and blend it again.


7. In a separate bowl (this does matter), mix the flour, baking powder, and salt.


8. Add about 1/3 of this dry mixture to the mixing bowl and mix just until it's combined.


9. Pour 1/2 of the pineapple mixture in to the mixing bowl and mix just until it's combined.


10. Add another 1/3 of the dry mixture to the mixing bowl and mix just until it's combined.


11. Pour the remaining pineapple mixture into the mixing bowl and mix just until it's combined.


12. Add the remaining flour mixture, mix it in, and scrape down the bowl and the beaters and blend it again. The resulting batter should be somewhat similar to pancake batter.


13. Pour this mixture into the cast iron skillet (or the 9X13 pan) and bake at 375 degrees for about 45 minutes.


14. Let it cool for 12-14 minutes (but not longer!).


15. Gently run a sharp knife gently around the edge of the pan (between the cake and the pan) to make sure none of the sides of the cake are stuck to the pan.


16. Invert a cooling rack on top of the cake, then grip both the cake and cooling rack and flip it over. Remove the pan and let the cake cool for 30-40 minutes while you clean up the kitchen.

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