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The Best Pineapple Upside Down Cake

I’ve tried quite a few Upside Down Pineapple Cake recipes. This recipe, courtesy of Simply Recipes, is hands down the best. The cake itself is heaven and the topping is rich and delicious. It is divine when served with whipped cream.

A few notes:  There is an option of using either all purpose flour or using a mix of all purpose / cake flour / ground almond.  I have always used just the regular all purpose flour and the cake turns out incredible.

In the original recipe, the brown sugar mixture for the topping is prepared on the stove and brought up in heat until it is bubbling. I usually just melt the butter and brown sugar, stir well, and call it good, either in the microwave or on the stove top. I just note this now if you were wondering if you could save a few minutes to skip that step. I do and it turns out great anyways.

The rest of my notes are regarding to how I prepare the cake.The original recipe uses a 2 inch deep cake dish. I prefer a thinner cake so I split the batter in two and use two slightly smaller cake plates (1 1/2 inch deep plates). Since I split the cake in two, I double the topping and divide it between the two plates.

My cook time is less than the original recipe because my cakes are thinner. If you prefer to only make one large, extra deep cake, please follow the original recipe at Simply recipes.

Overall I just like making two cakes instead of one because I feel like the cake to topping ratio is perfect that way, and you also have one cake to keep for yourself and one to give away to a friend. Enjoy!

The Best Pineapple Upside Down Pineapple Cake
Makes two 9″ cakes.

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Note: I used 1 1/2″ tall cake pans, which makes two cakes. If you use a 2″ tall cake pan you should be able to fit all the batter into one dish, but it will take longer to bake, about 1 hour and 15 minutes.


  • For the topping (for 2 cakes)
  • 2 cups brown sugar
  • 1 cup butter
  • 14 sliced pineapple rings (which is 1 1/2 20 oz. cans)
  • 14 maraschino cherries
  • For the cake:
  • 2 cups flour (Or 1 1/2 cups flour + 6 Tbsp. cake flour + 6 Tbsp. ground almond)
  • 3/4 tsp. baking powder
  • 1/2 tsp. salt
  • 1 3/4 cup sugar
  • 1 cup butter
  • 4 large eggs
  • 3/4 tsp. vanilla
  • 3/4 cup sour cream
  1. Prepare the topping: Melt the butter and brown sugar in a sauce pan over medium heat and stir until completely dissolved. Place the pineapple rings into the two prepared 9″ cake pans. Add a cherry inside of each pineapple ring. Divide the topping mixture in two. Pour topping over pineapple slices.
  2. Prepare the cake: Preheat oven to 325 degrees F. Whisk the flour, baking powder, and salt in a large mixing bowl. In a separate bowl, use an electric mixer to beat the sugar and butter together until light. Add eggs one at a time, beating after each addition. Beat in the vanilla. Add dry ingredients alternately with sour cream in 2 additions each, beating well after each addition. Divide batter in half. Pour cake batter over caramel and pineapple in pans.
  3. Bake cake until tester inserted into the center comes out clean, about 35-40 minutes. (See notes above if you used a 2″ cake pan – It will take longer to bake if so). Cool cake in pan on a rack for 10 minutes. Turn cake out onto a platter. Serve warm or at room temperature.
Recipe adapted from Simply Recipes.

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  1. Your recipe looks so good! =)
    I **love** Pineapple upside down cake!!

    I just pinned it to my Cake board.

  2. This sounds so good. It reminds me of the one my mom made. Pinned it.

    Wishes for tasty dishes,
    Linda @ Tumbleweed Contessa

  3. Mmmmmm…I've got a cup of coffee in my hand right now…I'd like a slice of this cake to go with it!

  4. I printed off the recipe and hopefully I will make this soon. I have one I just made that was very good but always willing to try another. Thanks, Andi

  5. I made this cake for the fair two years ago and the other one you posted for last year's last year and they both got second place! The funny thing is I made them both for the fair and never even tasted it myself (yes I'm crazy like that). So if you say this one is the best I think I'll make this one for us. 🙂

    1. This is the only recipe I make now when it comes to Pineapple Upside Down Cake. I'm a little tempted to take the other recipes down because this one is just that good.

  6. I made this last weekend and it was a MAJOR hit! I did tweak it some a bit, but not too much. My batter was way too thick so I added pineapple juice to thin it out, and I also threw in some coconut flavoring which was awesome. I've been requested to make this again very soon! Thanks!

  7. I was pretty skeptical to try this recipe because it calls for sour cream, but decided to try it anyways because your pictures look so delicious. I followed your recipe, except like the comment above, I added a tiny bit of pineapple juice. It made two round cakes so I brought one to work today and everybody loved it! This is the BEST pineapple upside down I’ve ever had hands down! Thank you for this recipe!

    1. Thank you for the feedback 🙂 I'm happy to hear that you liked the recipe. Sour cream is wonderful in a lot of baked goods. Don't let that put you off in the future. 🙂

    2. Your welcome:) I'm not a huge fan of cakes but your recipe is the best ever & this is now my favorite desert. You have made me love cake! And you also have made me a believer in sour cream into deserts lol.

    1. A cup of butter is 2 sticks or 227 grams or 8 ounces. Remember that Google is your friend and if you need a conversion you can search for it faster than I can do it for you. 😉

  8. I've tried for years to come up with a really good recipe for this for my husband, its his favorite. Finally after 12 years, this one is IT! I did do the almonds — added a nice flavor. I prepared the caramel topping as the Simple Recipe says to do. I did it all in one round cake pan. All I did was grease the pan to prepare it (recipe didn't say). I did this for Valentine's Day — so arranged the pineapple as a big heart in the middle of pineapple scalloped edges with the cherries in the nooks. Best cake ever! The sour cream helped so much.

  9. Just made this this afternoon – they smell wonderful, but I just went to take them out of he oven and they are nowhere near done. Is the baking time listed for one cake, or both at the same time? I was cooking both of them….I think that may have been where I went wrong…

    1. The baking time is for two cakes, but ovens are all different. Always test cakes for doneness with a toothpick 🙂

    2. Also, there are factors that I cannot know, like if your oven runs cold, what type of pan you used, what size it was, if you didn't preheat it long enough, if you opened up the door a lot during baking and let the heat out, etc. That's why you should always check with a toothpick 🙂

  10. I just baked your recipe and there was too much batter to put in two 9 inch pans so … I made a third "small" cake! I'm sure it will be great as I've made a coffee cake similar to this recipe that calls for sour cream and it's very tasty! The brown sugar, butter mixture will be very tasty and I'm anxious to try it. It's in the oven now! Can't wait! Thanks!

  11. This cake was wonderful! I think the sour cream makes a big difference in the texture and taste. The only thing I did different was I melt the butter directly in the baking dish in the oven while watching closely, then I sprinkle the brown sugar over the melted butter, place the pineapple all over, then place the cherries in. The butter absorbs up the brown sugar. This method leaves a little bit of grainy texture to a few bites usually around the edges, that I like!

  12. I love the adaptations! Good to know the timing when you split the batter into two pans. Sour cream makes all the difference, doesn't it?

  13. Just saves your recipe, hoping to try it this weekend….. My husband loves pineapples and so do I …..

  14. Hi! I'm thinking of trying this out this weekend, but wondering if there's anything else I can use as a substitute for the sour cream?

    1. Hi – I think you are best off Googling 'substitute for sour cream in baked goods' and try your luck. I have never substituted for sour cream so I have no recommendation on that. Good luck!

  15. Hello, I would love to try this recipe. But want to know, if not having cake flour and only using all purpose flour. Will that be fine or should go ahead and get some cake flour will it make a difference?

  16. I'm going to make this for my hubster's birthday because it's his favourite! Going to be one large cake! Thanks for the recipe x