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.
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.
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.
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.
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.
When the butter is melted, add in 1/2 cup brown sugar. Stir it together to dissolve and remove it from the heat.
In your mixing bowl, beat together 1/3 cup shortening and 1 cup sugar until creamed together. Beat in 2 eggs.
Mix in half of your dry ingredients.
Mix in 2/3 cup milk
Mix in the remaining dry ingredients and finally add in 1 1/2 teaspoon vanilla.
Grab your pineapple and spread it over the bottom of the skillet with the butter and brown sugar.
Gently spread the batter over pineapple.
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!
Cool the cake completely.
Enjoy!
Did you Make this Recipe? I’d love for you to give me a 5 star rating in the recipe card below. If you share it on Instagram, please tag me! You can also post it to my Facebook Page.
Old-Fashioned Pineapple Upside Down Cake
Ingredients
- ⅓ c butter, unsalted
- ½ c brown sugar
- 14 oz crushed pineapple
- 1 ⅓ c all-purpose flour
- 2 teaspoon baking powder
- ½ teaspoon salt
- ⅓ c shortening
- 1 c sugar
- 2 eggs
- ⅔ c milk
- 1 ½ 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
Nutrition
If nutritional values are provided for this recipe, they are an estimate and will vary depending on the brands of ingredients you use. The values do not include optional ingredients or when ingredients are added to taste or for serving. If nutritional values are very important to you, I suggest using your favorite nutritional calculating tool with the brands you use.
Unit Conversions:
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This is a keeper. Thank you for sharing!
So glad you liked it!
I have made this several times just as it is to rave reviews from everyone, but the last time I didn’t have any pineapple. I did have a can of fruit cocktail, so I used that, and everyone loved it So now I’m going to try it with peaches. However, I don’t think anything will quite match the original.
I used fresh pineapple, chunks sliced thin. I melted the butter in a saucepan and then added the pineapple and cooked for about 3 minutes. Then I added 2/3 c brown sugar and after brown sugar melted I cooked about another minute. I pored this in my cast iron skillet and carefully added batter on top. It only needed 35 minutes to cook. It was absolutely delicious! I’ll definitely make again!
I made this tonight. It was my first time making pineapple upside down cake and I found it to be very easy to make. This cake is a hit in my house!!
So glad you liked it!
Constance, this was delicious. I followed the recipe exactly, absolutely no changes made. This tasted just like the ones my dad used to make. Of course, we had to eat it with vanilla ice cream on top so it was like eating it with him. Thank you so much for the recipe and the wonderful memories.
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.
Hi Maria! Thank you for bringing that to my attention. I am not sure what was causing that, but I believe I have fixed the issue now.
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.
Wonderful! I am so happy to hear that :)
What is I’m making this in a 10×13 rectangular pan? How do I measure the ingredients for that?
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”
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!😋
That is the best part! :D
So yummy!! I didn’t have shortening so I used butter. Best pineapple upside down cake we have had
Is the flour plain or self rising?
It is all-purpose (plain) flour
I don’t own a cast iron skillet can I use something else???
Yes, see the note in the recipe card.
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😊
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!
So basically you made a different cake. Glad it was delicious though!
👏🏻Make👏🏻this👏🏻cake! Delicious. Moist. Nice crisp on the edges. So good.
So glad you liked it!
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.
Can I say DELICIOUS!!!
I was trying to describe the fresh pineapple taste – which I love. Thank you so much! I made this cake in an old round cake pan !!! Fantastic ‼️
So glad you liked it!
Using crushed pineapple is such a good idea! This looks so good. An oldy, but a goody!
Wow this looks really delicious! go to try out this recipe (:
Love those caramelized pineapple bits in the bottom of the pan! I've never mad pineapple upside down cake before. This needs to be rectified.
My recent post Raspberry Lime Cupcakes #SundaySupper
I have never made an upside down cake before, but this looks SO good!
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
Gorgeous gorgeous cake and with lovely flavors going on! Looks like a must try for sure :)
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!
Anything that starts with butter and brown sugar in a skillet is bound to be good. I love the last picture. Simple and elegant.
Hey, at least you used a fork for the pineapple bits. I'd just get in there with my fingers.
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!
You are my cast iron skillet hero! I love this. Looks amazing.
I can't believe I've never made a pineapple upside down cake! This will need to be my first… love it!!!
I love the idea of a pineapple upside down cake made with crushed pineapple! This is one of my dad's favorite cakes!
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 ;)
I like that you used crushed pineapple instead of rings, easier to nom!
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.
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.
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.
I had one that subbed coconut oil for butter on my bday…so good!
The classics never go out of style, and this one looks fantastic.
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 =)
Really?! That is the only way I have ever seen it made! How funny! You definitely need to give it a try :)
Thank you for participating this week! I'll have to give this a try.