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.

Disclosure – I may get a small commission for purchases made through affiliate links in this post.

Key to Success #1 – Use a Big Skillet
This Pineapple Upside Down Cake needs a BIG skillet.
I recommend making this fruity cake in a 12-inch cast iron skillet.
You might be able to get away with an 11-inch skillet if it’s deep enough.
If you use a 10-inch or smaller skillet, a baking sheet beneath it to catch the drips is a good idea.
This recipe calls for a cast iron skillet, but if you don’t have one, you can also make this cake in a 13×9-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 incorporating all of the delicious pineapple juice into the cake batter for added flavor.
You can also use pineapple tidbits in place of the pineapple rings.
When I want more pineapple in every bite, I frequently use pineapple tidbits.
However, it is not nearly as attractive.

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.
Pin this Pineapple Upside Down Cake recipe to your favorite Fruity Dessert board or your Pineapple Dessert board.


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.
Ingredients
- 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
Instructions
- 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.
- 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.
- 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.
- 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.
- 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.
Nutrition Information:
Yield: 8 Serving Size: 1 gramsAmount Per Serving: Calories: 681Total Fat: 20gSaturated Fat: 11gTrans Fat: 1gUnsaturated Fat: 8gCholesterol: 83mgSodium: 608mgCarbohydrates: 120gFiber: 1gSugar: 88gProtein: 7g
Nutrition Information Provided For Educational and Informational Purposes Only.