Old-Fashioned Pineapple Upside Down Cake

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You’ll love this pineapple upside down cake using crushed pineapple. Not only is it delicious, but it is much easier to serve than using the slices.


How to make good old-fashioned Pineapple Upside Down Cake from A Good Life Farm

This cake has been my favorite cake of all time since I was a kid. I often requested this for my birthday, and now-a-days my daughter does the honors when it rolls around.

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To begin, preheat your oven to 350 degrees.

In a 10 inch cast iron skillet, melt 1/3 cup of butter over very low heat.

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Meanwhile, drain a 14 ounce can of crushed pineapple. Press the excess juice from the pineapple as well. You want this as dry as possible. Set aside.

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In a bowl, combine 1 1/3 cup all-purpose flour, 2 teaspoon baking powder and 1/2 teaspoon salt. Stir together and set aside.

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When the butter is melted, add in 1/2 cup brown sugar. Stir it together to dissolve, and remove it from the heat.

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In your mixing bowl, beat together 1/3 cup shortening and 1 cup sugar until creamed together. Beat in 2 eggs.

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Mix in half of your dry ingredients.

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Mix in 2/3 cup milk

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Mix in the remaining dry ingredients, and finally add in 1 1/2 teaspoon vanilla.

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Grab your pineapple and spread it over the bottom of the skillet with the butter and brown sugar.

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Gently spread the batter over pineapple.

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Bake this for 40-50 minutes or until it tests done with a toothpick. Allow it to rest in the skillet for a couple minutes, then turn it out onto your platter.

I love this part…the little bits of pineapple that OOPS! Get left in the pan. Let me take care of this real quick!

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Cool the cake completely.

How to make good old-fashioned Pineapple Upside Down Cake from A Good Life Farm

Enjoy!

How to make good old-fashioned Pineapple Upside Down Cake from A Good Life Farm

Did You Make This Recipe? I would love for you to rate it in the recipe card, and I’d love to hear your thoughts!

How to make good old-fashioned Pineapple Upside Down Cake from Cosmopolitan Cornbread

Old-Fashioned Pineapple Upside Down Cake

Constance Smith – A Good Life Farm
You’ll love this pineapple upside down cake using crushed pineapple. Not only is it delicious, but it is much easier to serve than using the slices.
4.70 from 131 votes
Prep Time 10 mins
Cook Time 1 hr
Total Time 1 hr 10 mins
Course Cakes, Sweets, Treats & Desserts
Cuisine American
Servings 8
Calories 428 kcal

Ingredients
  

  • 1/3 c butter, unsalted
  • 1/2 c brown sugar
  • 14 oz crushed pineapple
  • 1 1/3 c all-purpose flour
  • 2 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1/3 c shortening
  • 1 c sugar
  • 2 eggs
  • 2/3 c milk
  • 1 1/2 teaspoon vanilla extract

Instructions
 

  • To begin, preheat your oven to 350 degrees.
  • In a 10 inch cast iron skillet, melt the butter over very low heat.
  • Meanwhile stir the flour, baking powder and salt together in a bowl. Set aside.
  • To the melted butter, add the brown sugar. Stir together and let the brown sugar dissolve.
  • Remove from heat.
  • In a mixing bowl, beat together the shortening and sugar until creamy.
  • Add in the eggs, and mix well.
  • Mix in half of your dry ingredients. Then add in the milk, and finally the remaining dry ingredients.
  • Stir in the vanilla. Beat for just a minute until smooth.
  • Press any excess liquid from the pineapple and then spread the pineapple over the bottom of the skillet.
  • Gently pour the batter over the top and smooth the top.
  • Bake for 40-50 minutes or until it tests done with a toothpick.
  • Allow it to cool a couple minutes in the skillet, then turn it out onto a platter.
  • Cool completely, and enjoy!

Notes

If you do not have a cast iron skillet, this can be made in a round cake pan. Simply melt the butter before adding it to the pan. Do the same from there.

Nutrition

Serving: 1cCalories: 428kcalCarbohydrates: 63gProtein: 5gFat: 18gSaturated Fat: 8gPolyunsaturated Fat: 3gMonounsaturated Fat: 6gTrans Fat: 1gCholesterol: 64mgSodium: 341mgPotassium: 152mgFiber: 1gSugar: 47gVitamin A: 354IUVitamin C: 5mgCalcium: 115mgIron: 2mg

Nutritional information is auto-generated and the accuracy is not guaranteed.

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42 thoughts on “Old-Fashioned Pineapple Upside Down Cake”

  1. HI. There is a problem with the printable version of the recipe. The ingredients print out fine but the instructions disappear. I had to keep my laptop open on the counter when I made the cake but it was delicious.

    Reply
  2. This was the best cake I’ve ever had. I used fresh pineapple it was delicious. I’m actually making it again today 2x’s in 1 week. Thanks for the amazing recipe. I love the crispy edges from the cast iron skillet.

    Reply
  3. Simple & Delicious! Just the way I love to cook. I added a little unsweetened coconut to the batter before baking and, as I said “DELICIOUS”

    Reply
  4. This was simply Wonderful, I have made my second one, it is so good! Thank you for the recipe and I love it with the crushes pineapple. I also love the gooey edges!😋

    Reply
  5. So delicious! I used a fresh pineapple and my 10” cast iron skillet. Thank you! I posted photos and recipe link to The Blue Willow Pantry Facebook page😊

    Reply
  6. I made this today, but cut the recipe in half so that I could bake it in my Ninja Foodi. I also used Featherweight no sodium baking powder and added nearly 1/2 cup of sour cream. I also used oat milk and organic coconut oil. I added @ 15 chopped raspberries to the brown sugar/butter mixture. Thank you so much for giving me a recipe I could actually use in my Foodi! It is light, fluffy and delicious!

    Reply
  7. Hello Diana! I looked back over and saw what you were talking about with the missing line of instructions. Thankfully it was correct in the printable version, but I have made that correction. I hope the cake turned out great for you! Let me know how the substitution of the butter for the shortening worked out.

    Reply
  8. Pineapple Upside Down Cake is my #1 favorite cake too! We make it for Christmas dinner dessert & I make it for special occasions! I use pineapple rings, but I might use crushed next time so I can pick up the bits like you! Mmmm

    Reply
  9. Pineapple upside down cake has got to be one of the best old fashioned cakes. It look amazing Constance, and so lucky to have someone bake it for you!

    Reply
  10. Constance, You've brought back so many delicious memories. We used to bake a pineapple upside down cake religiously while I was growing up since it was my father's favorite cake (that and Boston Cream Pie). There's just nothing quite like this classic cake!

    Reply
  11. I love the idea of a pineapple upside down cake made with crushed pineapple! This is one of my dad's favorite cakes!

    Reply
  12. Oh, the crushed pineapple would make it so much easier than trying to lay rings down all pretty. I end up buying fresh pineapple and cutting it in wedges and laying it out grid like. I feel like I'd have to add some marashino cherries though just for that clasic look ;)

    Reply
  13. I so very much like this recipe with the crushed pineapple instead of those sliced rings. And I know I'd be like you to take care of any bits that clung to the pan.

    Reply
  14. Pineapple upside down cake is one of my favorites too, Constance, but I usually use the little rings of pineapple. I love your version with the crushed pineapple. I'll bet it makes the cake even more moist.

    Reply
    • Using the sliced pineapple is pretty, but I find that it is a pain in the hiney to slice the cake with those on top. Using the crushed pineapple is much easier when it comes to serving time.

      Reply
  15. I've never seen a pineapple upside down cake baked in an iron skillet. You are so clever, Constance! Thanks to you I've got another scrumptious to-do in my newly acquired iron skillet =)

    Reply

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