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Pineapple Upside Down Cake | Beyond Frosting

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March 12, 2025
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This pineapple upside-down cake is just like Grandma used to make. It’s a moist yellow cake baked over caramelized pineapple, dotted with maraschino cherries, and flipped for a beautiful top with minimal effort.

I love making upside-down cakes for special occasions, and they’re so easy!

Overhead view of a pineapple upside down cake on a parchment-lined cutting board.

Old-Fashioned Pineapple Upside-Down Cake

My grandmother inspired this pineapple upside-down cake. Well, her original recipe did! The first time I made it, my mom and I set out to decipher Grandma’s notes on the recipe card, which were… vague, to say the least. Over the years, I’ve continued to fill in the gaps and add my own spin to it, finally settling on the version I’m sharing today. I like to think this updated version would make her proud

This cake is soft and fluffy, topped with rich caramelized pineapples and cherries just like the classic recipe. I still catch my breath before turning over an upside-down cake, anticipating how it’ll turn out. What I love about this recipe is that there aren’t any surprises. I’m sharing my tips so that yours will come out perfect too.

A slice of pineapple upside down cake partially removed from the rest of the cake with a cake server.A slice of pineapple upside down cake partially removed from the rest of the cake with a cake server.

Ingredient Notes

In addition to your typical baking ingredients like flour, baking soda, and vanilla, this easy upside-down cake recipe uses a handful of key ingredients between the caramelized pineapple topping and the cake itself. I go over these below.

You’ll find the full printable ingredients list and recipe details in the recipe card underneath the post.

  • Brown Sugar – Light or dark brown sugar, lightly packed. You’ll use it in the cake and in the topping. I don’t recommend granulated white sugar, at least for the topping. For the caramel to turn out correctly, it needs the molasses found in brown sugar. 
  • Pineapple Slices – Canned pineapple rings are the classic choice. Pat the slices dry before you start and reserve the leftover juice for the cake batter. If you’re using fresh pineapple slices, you’ll need to buy pineapple juice separately.
  • Maraschino Cherries – Another classic topping for an upside-down cake. You could use fresh pitted cherries if you prefer.
  • Sour Cream – Full-fat sour cream adds loads of moisture to cake recipes. If you don’t have sour cream, Greek yogurt is a good substitute.
Pineapple upside down cake ingredients with text labels overlaying each ingredient.Pineapple upside down cake ingredients with text labels overlaying each ingredient.

Julianne’s Recipe Tips

  • Use room temperature ingredients. Make sure that the butter and eggs are at room temperature so they’re more easily incorporated.
  • Creaming the butter. It’s important to incorporate air into the batter to help the cake rise, and if the butter and sugar are not creamed well, the cake may not rise properly and can end up dense.  
  • Try not to disturb the pineapple. While adding the cake batter to the pan, do your best not to disturb the pineapple layer underneath. I like to dollop the batter over the pineapple and cherries, then add the rest of the batter and smooth it out with a spatula.
  • Don’t let the cake cool completely in the pan. Just like baking a bundt cake, it’s important not to let an upside-down cake cool fully in the cake pan. Doing so can cause the caramel to harden and the cake to get stuck in the pan.
  • To avoid a soggy upside-down cake, pat the canned pineapple dry before you add it to the pan, to avoid too much moisture in the topping. Also, it’s best to serve this cake the same day as the fruit softens the top with time. See below for storing and freezing directions if needed.
Side view of a slice of pineapple upside down cake being lifted from the rest of the cake with a cake server.Side view of a slice of pineapple upside down cake being lifted from the rest of the cake with a cake server.

How to Make a Pineapple Upside-Down Cake

These are the steps to make a picture-perfect pineapple upside-down cake from scratch. Scroll down to the recipe card for the printable directions.

  • Make the topping. Add butter to a greased 9” cake pan and place that into the preheating oven. Once the butter has melted, stir in the brown sugar until it’s well combined.
  • Add the pineapple. Next, arrange the pineapple rings over the brown sugar mixture, gently pressing them into the bottom of the pan. Place a maraschino cherry into the center hole of each pineapple slice.
Brown sugar mixture spread into the bottom of a cake pan.Brown sugar mixture spread into the bottom of a cake pan.
Prepare the topping.
Pineapple rings and maraschino cherries arranged over top of the brown sugar base inside a round cake pan.Pineapple rings and maraschino cherries arranged over top of the brown sugar base inside a round cake pan.
Add the pineapples and cherries.
  • Combine the cake ingredients separately. Now, whisk the pineapple juice, sour cream, and vanilla together in a bowl. Separately, whisk the flour with the baking soda and salt. Then, beat butter with brown sugar in the bowl of a stand mixer until it’s fluffy, and add the eggs one at a time, mixing in between.
  • Mix the batter. Slowly alternate adding the flour mixture and sour cream mixture to the creamed butter and sugar, starting and ending with the flour.
Wet ingredients combined in a glass bowl with a hand mixer.Wet ingredients combined in a glass bowl with a hand mixer.
Combine the wet and dry ingredients separately.
Yellow cake batter combined in a glass bowl with a hand mixer.Yellow cake batter combined in a glass bowl with a hand mixer.
Mix to make the batter.
  • Bake. Afterward, scoop the cake batter into your prepared baking pan and spread it in an even layer. Bake this upside-down cake at 350ºF for 35-40 minutes. When the cake is lightly golden, test the center using a toothpick. If it comes out clean, the cake is done.
  • Cool and flip. Let the cake rest in the baking pan for 10-15 minutes. To invert an upside-down cake, place a plate over the cake pan, and use both hands to flip the cake over and out onto the plate (see below).
Cake batter spread over the pineapple topping inside a round cake pan.Cake batter spread over the pineapple topping inside a round cake pan.
Spread the batter in the pan.
Baked upside down cake inside a round cake pan.Baked upside down cake inside a round cake pan.
Bake, cool, and flip!

The Trick to Flipping an Upside-Down Cake

A pineapple upside-down cake should be warm, but not fresh from the oven when you flip it onto the plate. To avoid sticking, I don’t recommend leaving the cake in the pan for longer than 15 minutes. Don’t let the cake cool completely in the pan.

Before flipping the cake, loosen the edges a little using a sharp knife. Then, place a plate facing down over the cake pan. Grasp both sides of the plate and the pan firmly, and flip! You may need to gently tap the bottom of the pan to help the cake release.

Close up of pineapple upside down cake.Close up of pineapple upside down cake.

How to Store

  • Refrigerate. This pineapple upside-down cake is best enjoyed the same day it’s made. That being said, it’s fine to eat for up to 3 days. Store the cake airtight in the fridge to keep it fresh.
  • Freeze. To freeze an upside-down cake, wrap the cake whole or in slices in a double layer of plastic wrap. Freeze for up to 2 months. Thaw the cake in the fridge before serving. Freezing and thawing will affect the texture of the topping.
Print
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Description

This easy pineapple upside-down cake is a moist yellow cake baked over caramelized pineapple, dotted with maraschino cherries, and flipped for a beautiful top!

For the topping

For the cake

  1. Preheat the oven to 350° F. Spray a 9-inch cake pan with cooking spray.
  2. For the topping, Place butter in the cake pan and place in the oven to melt while it’s preheating. Remove from the oven and stir in brown sugar; mix until well combined. Place pineapple rings in a pretty pattern on top of the brown sugar mixture, pushing them down into the bottom of the pan. Place maraschino cherries in each hole of the pineapple rings, set aside.
  3. For the batter. In a small bowl, mix together the pineapple juice, sour cream and vanilla extract until well combined; set aside. In another small bowl, whisk together the flour, baking soda and salt. 
  4. In a large bowl of a stand mixer using a paddle attachment or using a hand mixer, beat the butter with the brown sugar on medium-high speed until light and fluffy, about 2-3 minutes.
  5. Add the eggs one at a time and mix on medium-high speed until well combined. Scrape the bottom and sides of the bowl after the addition of each egg. 
  6. With the mixer on medium low, add ⅓ of the flour mixture until combined, followed by half of the sour cream mixture. Repeat with an additional ⅓ of the flour, then the final portion of the sour cream mixture, and finally stir in the last of the flour mixture until the batter is just combined. Scoop the batter into the pan and carefully spread it out evenly, being careful not to disturb the pineapple slices.
  7. Bake at 350°F for 35-45 minutes until lightly golden brown on top. Test the cake for doneness by inserting a toothpick into the middle of the cake. If the toothpick comes out clean, the cake is done.
  8. Allow the cake to rest for 10-15 minutes to allow the caramel to settle and be soaked up by the cake. Gently run a knife around the edges of the cake. Put a plate on top of the pan, and use two hands to carefully invert the cake onto the plate. You may need to tap the bottom of the cake to help release it from the pan. Top with extra cherries if desired.

Notes

How to store:  This pineapple upside-down cake is best enjoyed the same day it’s made. That being said, it’s fine to eat for up to 3 days. Store the cake airtight in the fridge to keep it fresh.

Nutrition

  • Serving Size: 1 Slice
  • Calories: 452
  • Sugar: 38.5 g
  • Sodium: 248.7 mg
  • Fat: 23 g
  • Carbohydrates: 58.6 g
  • Fiber: 1 g
  • Protein: 4.6 g
  • Cholesterol: 104.1 mg

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