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Pineapple Upside Down Cake

Pineapple Upside Down Cake is a classic cake that is unlike any other. The combination of pineapple with the delicious brown sugar caramel topping makes this cake a real treat.

Prep Time - 20 mins
Cook Time - 40 mins
Total Time - 1 hr

Course: Dessert
Cuisine: American
Keyword: cake, pineapple
Servings: 8 servings
Author: Jennifer

  • 2 1/2 cups all-purpose flour
  • 2 cups sugar
  • 1 cup milk
  • 2/3 cup pineapple juice reserved from pineapple slices
  • 1/4 cup Crisco shortening
  • 1 Tbsp baking powder
  • 2 tsp vanilla extract
  • 1 tsp salt
  • 2 eggs
  • 1 can (20 oz) sliced pineapple juice reserved
  • 1/2 cup butter softened
  • 1 1/3 cup brown sugar
  • 1 jar Maraschino cherries
  1. Preheat oven to 350ºF. Drain can of sliced pineapple into a measuring cup.  If juice measures less than 2/3 cup, add water to equal 2/3 cup.
  2. In medium bowl, cream together 4 tablespoons of butter, shortening, and sugar. Add eggs and vanilla extract. Slowly mix in salt, baking powder and flour. Add milk. Add pineapple juice and beat until just combined. 
  3. In 12-inch cast iron skillet, melt remaining 4 tablespoons of butter over medium heat. Coat skillet well. Sprinkle brown sugar evenly over the butter. Do not stir. 
  4. Let sugar dissolve then turn off heat. Layer pineapple slices over the brown sugar/butter mixture then place cherries in the middle of pineapple slices. 
  5. Pour cake batter evenly over the pineapple and gently spread to even out the top. Bake 30-45 minutes until a toothpick inserted into the center comes out clean.
Key to Success #1 – Use a Big Skillet
This Pineapple Upside Down Cake needs a BIG skillet – a 12-inch cast iron skillet. If might be able to get away with an 11-inch skillet if it’s plenty deep, but if you choose to use a 10-inch or smaller skillet I’d suggest putting a baking sheet underneath it to catch the drips.

I really prefer a cast iron skillet for this recipe but if you don’t have one you can also make this cake in a 13X9-inch baking dish.

Key to Success #2 – Amp Up The Pineapple
Instead of just layering the pineapple slices in this Pineapple Upside Down Cake, we’re putting all that yummy pineapple juice into the cake batter for even more flavor.

You can also use pineapple tidbits in place of the pineapple rings. I often use the pineapple tidbits when I want to have more pineapple in every single bite. It’s not nearly as pretty though.

Key to Success #3 – Flip Right Away
After the cake is fully baked (make sure you do the toothpick test!) you’ll want to run a sharp knife around the outside of your cake then flip it over onto a large platter right away.

If you wait too long to flip, the brown sugar will start to cool down and it’ll be harder to get the cake out of the pan. If you have a pineapple or two that stick to the bottom of the pan, you can just loosen them up and put them back into place. It’ll still be delicious!

I hope you’ll try this easy and delicious dessert.

Please share the image below on Pinterest!


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