Have you ever been invited to someone’s house for dinner and loved a dish so much that you had to hold yourself back in order not to eat it all by yourself? Well, I have. This upside-down pineapple cake was one of the many desserts that Eva and Carey made for us during the British Virgin Islands workshop back in January. Actually, it was the dessert for the first evening’s dinner.

Close view of a person holding an Upside Down Pineapple Cake

I loved it so much that if it weren’t inappropriate I would have eaten it all by myself. Imagine, how would that go on the first night with a group of people that I have never met before?! It was such a surprise to me, because I wouldn’t even call pineapple as one of my favorite fruits. But this cake paired with a light cake batter and brown sugar & butter topping blew my socks off. As soon as I made it back home I made it for myself. Since then, it has become our favorite cake.

Overhead view of a Pineapple Cake
Overview of a slice of Upside Down Cake

Eva got the recipe from Smitten Kitchen who got it from the Gourmet Magazine that was published back in 2000. It was a success on the very first try. So the recipe is 100% foolproof.

However, after making a couple of times I learned some things that may help you get a perfect pineapple upside down cake in your first try.

Pineapple Upside Down Cake Recipe – Baker’s Notes:

So here are the baker’s notes:

Use fresh pineapple: I have made this using pineapple from a jar and it ended up being too sweet for our taste. Even during the winter months you can find fresh pineapple in most supermarkets. For best results, I recommend using fresh pineapple.

Overhead view of two slices of Upside Down Pineapple Cake

You can use a 10-inch cast iron skillet or a 9-inch cake pan: The cake you see in the photos was made in a 9-inch cake pan, but I have made it in a 10-inch cast iron skillet as well. Obviously, 10-inch cake was a little thinner, but still, it was great.

First make the batter and then the butter-sugar topping: On my first try, I made the topping first and then set it aside while making the batter. However, I think it is better to make the butter and brown sugar topping right before baking the cake. Plus, if you are short on time you can make the batter a day in advance, keep it sealed with plastic wrap in the fridge, and bake it the next day. When it is time to bake, simply make the topping, arrange the pineapples on top, and pour the batter.

Overhead view of one slice of partially eaten Upside Down Pineapple Cake
Person about to cut an Upside Down Pineapple Cake

Arranging the pineapple slices: Keep in mind that the way you arrange pineapple slices is important as they make the “face” of the cake. Feel free to arrange them as close to one another as possible and fill the empty spots with smaller slices.

Wait 5 minutes before removing the cake pan: Once the cake comes out of the oven, let it cool for 10 minutes. After then, invert it onto the cake platter. However, instead of removing the cake pan right away allow it sit for 5 minutes so that the brown sugar will have time to fully drizzle over the cake while the cake pan is still intact.

Overhead view of Upside Down Pineapple Cake with one slice removed and placed on a plate

Serve it warm: Quite honestly, I am not a warm dessert person but this cake is an exception. Though it is still delicious at room temperature, it is exceptionally tasty when it is warm. Feel free to store it in the fridge in an airtight container. When ready to serve, let it come to room temperature, cut yourself a slice, and microwave it for 15-20 seconds before serving.

Can you make pineapple upside down cake the day before?

While I personally like this pineapple cake on the day it is made, you can make it the day before. Simply, bake it as directed, let it fully cool to room temperature, and store it in the fridge.

When ready to serve, slice it up, and warm up each slice for 15-20 seconds in the microwave.

Other Fruity Desserts You Might Also Like:

Upside-Down Pineapple Cake

5 from 1 vote
Yields8 servings
Prep Time15 minutes
Cook Time45 minutes
Total Time1 hour
Upside Down Pineapple Cake for a scrumptious treat perfect for the tea time. Adapted from Smitten Kitchen’s recipe, this pineapple cake has the most delicious crumb to fruit ratio with an addictive brown sugar glaze. Easy to make with everyday ingredients you most likely have in your pantry.

Ingredients 

To make the batter:

  • 1 1/2 cups (7 1/2 ounces) all purpose flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 6 tablespoons (3 ounces) unsalted butter, at room temperature
  • 1 cup (7 ounces )granulated sugar
  • 2 large eggs, at room temperature
  • 1 teaspoon vanilla
  • 1/2 cup unsweetened pineapple juice
  • Lavender leaves, optional

To make the topping:

  • 1/2 medium pineapple, peeled, cored, and sliced into small size (as seen in the photos)
  • 6 tablespoons (3 ounces) unsalted butter
  • 3/4 cups (5.25 ounces) light brown sugar

Instructions 

  • Preheat the oven to 375 degrees. Lightly butter and flour a 9-inch cake pan. I used one with a removable bottom.

To make the batter:

  • Mix together the flour, baking powder, and salt together in a small bowl and set aside.
  • Place the butter and sugar in the bowl of a standing mixer (or a hand mixer would work as well) attached with the paddle attachement. Mix in medium speed until totally combined and creamy. While the mixer is running, add eggs one at a time beating well after each addition. Stir in the vanilla and mix for 15-20 seconds.
  • Turn the speed to low and add half of the flour mixture. Mix until barely combined. Beat in the pineapple juice and the rest of the flour mixture. Mix until just blended. Do not overmix. Do not be alarmed if it looks slightly curdled. Set aside.

To make the topping:

  • Melt the butter in a saucepan. Add in the brown sugar. Let it simmer, while stirring it frequently 3-4 minutes.

To assemble the cake:

  • Pour the butter-brown sugar mixture in the prepared pan. Arrange pineapple slices over the mixture in concentric circles, overlapping pieces slightly. Spoon the batter over. Using the back of a spoon spread it evenly throughout the cake pan. Place it on a sheet pan and bake for 40-45 minutes or until a toothpick inserted comes out clean.
  • Let it cool for 10 minutes. Place a serving plate upside down onto the pan and turn plate and pan over. Let it sit for 3-5 minutes so the brown sugar topping can drizzle over the cake. Remove pan. Cool 15 minutes. If preferred, garnish it with fresh lavender leaves.
  • Serve while it is still warm.
  • Store covered in the fridge. Bring it to room temperature and serve. If preferred, warm it up for 15-20 seconds in the microwave.

Nutrition

Calories: 483kcal | Carbohydrates: 77g | Protein: 4g | Fat: 18g | Saturated Fat: 11g | Cholesterol: 86mg | Sodium: 204mg | Potassium: 149mg | Fiber: 1g | Sugar: 57g | Vitamin A: 617IU | Vitamin C: 29mg | Calcium: 100mg | Iron: 2mg

Nutrition information is automatically calculated, so should only be used as an approximation.

Additional Info

Course: Cake
Cuisine: American
Tried this recipe?Mention @foolproofliving or tag #foolproofeats!

 Adapted from Smitten Kitchen’s Pineapple Upside-Down Cake recipe.


About Aysegul Sanford

Hello Friend! I'm Aysegul but you can call me โ€œIce." Iโ€™m the cook/recipe-tester/photographer behind this site.

If youโ€™re looking for approachable, yet creative recipes made with everyday ingredients, youโ€™ve come to the right place. Here, weโ€™re all about recipes thatโ€™s been meticulously tested to provide you with a truly foolproof cooking experience regardless of your level of cooking.

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22 Comments

  1. Hi Aysegul, unfortunately my upside down cake wasn’t terribly successful. I followed instructions and tips to the T but it didn’t look anything like yours! The butter/sugar topping seemed to just stay on the top and totally masked the pineapple slices. I probably used too dark a brown sugar to begin with. In your pictures, the pineapple slices seemed to be sitting atop the butter/sugar topping, but that wasn’t the case with mine!

    1. I am very sorry to hear that it didnโ€™t look like the one in the photos. I had the same issue when I made this same cake with blood oranges.
      When I made this cake I remember that the key was to let the cake sit upside down for a little while with the cake tin intact. I know you said that you followed it to the T, so I really do not know why it didnโ€™t work. In terms of brown sugar, I think both light and dark would work in this recipe. I guess, it is a preference.

      I went back and read the recipe to see if I made a mistake, but it is correct.. I will make this recipe one more time just to test it again just to be sure.

      Once again, I am very sorry that it didnโ€™t work out for you. Still, I am hoping that at least it tasted good.

      1. Thanks for your message. Trying again today and just put another into the oven, crossing both fingers and toes!!

      2. How was it Jacqueline? I am wondering.
        We are currently moving into our new house, but as soon as I have my baking supplies I am going to give this recipe another try.
        Meanwhile, I am here if I can help in any way.
        Please let me know. ๐Ÿ™‚

      3. Dear Aysegul, it was a success second time around!! I am soooo pleased and so grateful to have been inspired and encouraged by your post.
        Ingredients: I changed the sugar from dark brown Demerara to light brown cane sugar. That made a big difference to the colour of the topping. I also cut down on sugar quantities in both the topping and batter by one-third each. Personal preference for less sweet cakes. Added the rum and cardamom powder as per Smitten Kitchen’s recipe (but reduced pineapple juice by a commensurate amount of spiced rum). I used strained fresh pineapple juice. I think because there was less topping sugar, there was less cake soaked in syrup and more of a distinct fluffy cake layer which went down well in this household.
        Method: I left it to cool once out of the oven for only 3 min. Then turned it upside down and left it for 15 min before opening the springform. For the 1st cake, I left it to cool for 10 min before inverting it which may have been too long in my cold kitchen, i am guessing the topping set too much so that it didn’t drizzle down when I inverted it.
        I am going to tag you in my Instagram post so that you can see how it turned out. Big kisses!

  2. Gorgeously shot as always! There is something so deliciously retro about an upside down cake, I love them! I can just imagine how good this tastes with juicy caramelised pineapple . I make a blood orange version and it took ages to get the recipe right. Can’t wait to try this, Aysegul! x

    1. Hi Louise… I love that you call it retro. I have never thought about it that way. But I can see how you feel that way. I think it is super cool.. Ha ha..
      Thanks my friend!
      PS: I need the recipe for the blood orange version. I cannot seem to be able to get my ratios right. ๐Ÿ™‚

  3. That is one gloomy pineapple cake ๐Ÿ™‚ jokes aside, it looks nice and easy to make i guess. It would be a nice touch over a sunday breakfast.

    1. Dear Alp… Thank you so much. Yes, it is out of this world delicious. And yes, I cannot imagine a better cake for a sunday morning breakfast table served with a ince belli glass of freshly brewed Turkish tea. ๐Ÿ˜‰

  4. This looks absolutely gorgeous, Aysegul! You have me craving this cake so badly now <3 You arranged the slices so perfectly as well. Fabulous job, and wonderful tips!!

  5. I am bookmarking this post as this is my father-in-law’s favourite cake and his birthday is coming up.
    Beautiful photos, Ice, and thank you SO MUCH for all the tips. ๐Ÿ™‚
    xoxo

    1. YAY! I hope he will like it as much we do. I have struggled with upside-down cakes in the past, but this one is a really good recipe that works.
      Thank you for your kind words Pang. They mean so much to me. <3

  6. The way you’ve described it is making my mouth water. And it looks so beautiful too!

  7. This looks delicious and as luck would have it I have a pineapple in the kitchen. Beautiful photographs too.

  8. I admit I’m usually not an upside down-cake kind of girl, but you have me totally convinced that this is worth a try. It’s glamorous and cozy at the same time. Such helpful tips, such beautiful photos. It’s just lovely all around.

    1. Thank you Emily. <3
      Let me know how it turns out when you try it. I am sure your kids will love it. ๐Ÿ™‚

  9. This is my nemesis. Upside down cakes are my nemesis. I have already given up on them, never being able to make them come out right. Still, I might take back that decision and try this one…
    http://bloglairdutemps.blogspot.pt/

    1. Oh no! It is funny you say that because I feel that way about blood orange upside down cakes. I tried several recipes and haven’t been able to achieve a good result. They did taste good, but weren’t pleasing to the eye.
      However, this recipe is a good one. Just follow the steps and you’ll be fine. Let me know if you do. If you have any questions, I am here.
      Thanks Miranda!