Pineapple Upside Down Cake
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This is a light and fluffy homemade pineapple upside down cake recipe that’s so easy to mix up. An easy vanilla cake batter is baked with a brown sugar pineapple topping with maraschino cherries. The vanilla cake is made with melted butter, so this pineapple upside down cake recipe comes together in less than 30 minutes!
I have to admit pineapple upside down cake is not a cake I grew up on. In fact it’s only been a few years since I ever enjoyed a slice. But man was I missing out! For those of you who have enjoyed this cake for years then you know what I’m talking about.
There’s something magical about flipping the cake upside down after it bakes and revealing that beautiful caramelized pineapple topping with a maraschino cherry peeking in around each of the pineapple slices. And the brown sugar-butter mixture that coats the fruit is clearly my favorite part of this upside down pineapple cake. Yes let’s just say I am a big fan of pineapple upside down cake and I think you will be too once you take a bite.
This pineapple upside down cake recipe did take a few rounds of trial and error. I wanted a cake that could hold up underneath the heavy pineapple topping and not create a soggy sort of smushed sponge cake underneath. But I also wanted the perfect balance of fruit topping to cake.
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I started with using my vanilla cake batter as the jumping off point. I cut that recipe in half, but I found that using softened butter created too fluffy a cake and it didn’t have the perfect topping to cake ratio. I decided to try it with melted butter instead. And it was pure pineapple gold! It was the perfect cake to topping ratio. The best pineapple upside down cake recipe was born if I do say so myself.
By using melted butter instead of softened butter also meant I didn’t need to bust out my stand mixer and bring my butter to room temperature and cream it with the sugar. That meant this became a very easy cake to whip up and serve then I originally planned. I seriously love my stand mixer but I also love being able to make a cake with just a mixing bowl and a whisk. Call me lazy but I’ll call myself efficient. 😉
Table of contents
What is a pineapple upside down cake?
If you’re unfamiliar with this type of cake, this is a really fun retro cake to make! Let me break it down for you – basically the topping of the cake – melted butter, brown sugar, pineapple slices, and maraschino cherries get placed in the bottom of the cake pan. The cake batter is poured over the fruit mixture and then baked.
After it’s baked the cake is flipped upside down (hence the name!) revealing the pineapple topping. So it’s basically baked “upside down” and then flipped upside down as well.
Of course pineapple is the most famous of them all, but other fruits are often used to make an upside down cake.
A upside down pineapple cake really isn’t that old in “cake years”. Although there isn’t an exact date of when it first came about but it seems the 1920s when it started to make it first appearance.
And it was when this cake really gained popularity when the Dole company decided to run a contest for pineapple recipes. Apparently they received over 2500 recipes for it! Genius marketing there don’t you think?
Why The Recipe Works
- Made with melted butter so the batter mixes up quickly
- No mixer needed
- No yellow cake mix needed! Made entirely from scratch with simple ingredients
- Moist cake topped with brown sugar pineapple topping that is hard to beat
Ingredients Needed
- Unsalted butter
- Light brown sugar
- Pineapple slices – I used canned whole slices of pineapple, but you can definitely use fresh pineapple rings if you want instead of a can of pineapple. I use pineapple slices and not chunks which might make for a messy topping that doesn’t stay in place. I recommend blotting the pineapple slices dry before starting to remove any extra pineapple juice.
- Maraschino cherries – I used jarred maraschino cherries but I think fresh cherries might also work. If they are large I would recommend cutting them in half.
- Cake Flour – For a tender cake I used cake flour. If you don’t have any, read my full tutorial on how to make cake flour.
- Baking Powder
- Salt
- Eggs – Use room temperature eggs. Read my full tutorial on how to bring eggs to room temperature fast.
- Vanilla extract
- Buttermilk – If you don’t have any, check out my full tutorial on how to make homemade buttermilk.
- Granulated Sugar
- Oil – Use a neutral-tasting oil such as canola or vegetable oil.
For the topping:
For the vanilla cake:
How To Make Homemade Pineapple Upside Down Cake
Prepare topping. I like to first blot the pineapple sand cherries to remove excess liquid so it doesn’t add extra moisture to the cake. Pour the melted butter into the bottom of the cake pan then sprinkle brown sugar evenly over the melted butter.
Arrange the whole rings in sugar mixture (8 pineapple rings on the bottom, and cut the remaining 3 pineapple slices in half and place around the sides of the pan). Place a cherry in the center of each pineapple slice and in the center of the pan and around the sides.
Combine dry ingredients. Whisk together flour, baking powder and salt in a small mixing bowl and set aside.
Mix butter, oil and sugar. In a large mixing bowl, whisk together the melted butter, oil and sugar until combined.
Add eggs and vanilla. Add the eggs, beating well after the addition. Beat in vanilla.
Add dry ingredients alternately with buttermilk. Add the flour mixture to the creamed mixture alternately with buttermilk, beating well after each addition.
Bake. Pour batter into the prepared cake pan over the brown sugar-butter mixture and pineapple topping. Some of the pineapple slices will peek above the batter.
Bake 45 to 50 minutes or until toothpick inserted in center of cake comes out clean (don’t go all the way down or you will just get the brown sugar bottom) . Top will be a dark golden brown and spring back when touched. Cool 5 minutes. Loosen edges, and invert out onto a serving platter.
Heather’s Baking Tips
- Blot the pineapple slices and cherries first. This will ensure there isn’t too much liquid in the fruit and causing an overly wet cake.
- Grease your cake pan JUST in case. I’ve never had an issue with this cake sticking since there’s a whole lot of butter in the bottom, but I still give it a spray. Call it superstition. Old habit. But hey, a quick spray and I’ll know there’s definitely NO way this cake is sticking.
- Measure Your Flour Correctly – Too much flour in your measuring cup will result in a heavy, dry cake. I recommend using a kitchen scale and measuring by weight for best accuracy. But if using measuring cups, then be sure to spoon the flour into your cup and level it off, making sure to not pack the flour down into the cup.
- Use room temperature eggs. You want to make sure your eggs are cold going into the bowl, otherwise they might cause the butter to solidify. I place my eggs in a bowl of warm water for 10 minutes before I use them.
- Invert The Cake After About 5 Minutes In The Pan. Give the cake a few minutes to rest in the pan after baking but then invert the cake while warm before the topping sets up.
- Give It A Tap If Need Be. If the cake does appear to be losing some of the topping, then give it a tap when you’ve inverted it. And if all else fails, remove any of the fruit that stuck, and simply place it back on top. No one needs to be the wiser!
Storage Instructions
You can store the cake or leftovers in an airtight container, covered, for up to 3 days.
This cake freezes well. Freeze any leftovers by wrapping up any slices and freezing for 3 months. Thaw at room temperature, unwrapped, before serving.
Recipe FAQ’s
I think fresh pineapple slices would work instead of pineapple rings but I wouldn’t recommend chunks or crushed pineapple as it may make a messy topping that doesn’t stay in place but I haven’t tried it. I use and recommend canned pineapple rings.
It might be from excess liquid from your pineapple and cherries. Be sure to blot the pineapple rings and cherries before making the topping.
Yes you can and it will definitely help with any sticking issues with the fruit.
Yes you can but you may find it cooks a bit faster but you will get beautiful caramelized pineapple rings from the cast iron skillet!
More Recipes To Try
If you love this pineapple upside down cake recipe then here are more cake recipes to try! I love baking my hummingbird cake up this time of year as well! Made with my cream cheese frosting, it’s full of pineapple, coconut and pecans. Or try my Sock It to Me cake recipe made in a bundt pan with a pecan swirl.
Or my berry chantilly cake is also a show stopper. It’s better than Whole Foods! For more fruit-based cakes, try my strawberry pound cake or my peach cobbler pound cake.
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Pineapple Upside Down Cake Recipe
Ingredients
For the topping:
- 1 20 ounce can pineapple slices
- 19 maraschino cherries
- ¼ cup (4 Tbs., 57 g) unsalted butter, melted
- ⅔ cup (143 g) packed light brown sugar
For the cake:
- 1 ½ cups + 2 Tablespoons (195 g) cake flour spooned and leveled
- 1 ½ teaspoons baking powder
- ¼ teaspoon salt
- ¼ cup (4 Tbs., 57 g) unsalted butter, melted
- ¼ cup (60 ml) canola oil
- 1 cup (200 g) granulated white sugar
- 2 large eggs room temperature
- 1 ½ teaspoons vanilla extract
- ⅔ cup (160 mL) buttermilk
Instructions
- Prep oven and prepare pan. Position a rack in the center of your oven and preheat oven to 350°F (180°C). Spray 9-inch (23 cm) cake pan with non-stick cooking spray. You can also line the bottom of the cake pan with parchment which will help with any sticking issues.
- Prep fruit. Drain pineapple. Place pineapple slices and cherries on a plate and blot with a paper towel to remove excess moisture. Cut 3 pineapple slices in half. 1 20 ounce can pineapple slices 19 maraschino cherries
- Prepare topping. Pour the melted butter into the bottom of the cake pan, swirling to coat the entire bottom. Sprinkle the brown sugar over the top of the butter. Place the whole pineapple slices on top of the brown sugar (8 on the bottom of the pan, and with the remaining cut pineapple slices, place each pineapple half slice around the sides standing upright alternating between the slices on the bottom. Place a cherry in the center of each pineapple slice and in between the pineapple slices and around the sides. ¼ cup (4 Tbs., 57 g) unsalted butter, ⅔ cup (143 g) packed light brown sugar
- Combine dry ingredients. Whisk together the cake flour, baking powder and salt in a small mixing bowl and set aside. 1 ½ cups + 2 Tablespoons (195 g) cake flour 1 ½ teaspoons baking powder ¼ teaspoon salt
- Cream butter and sugar. In a large mixing bowl, whisk together the melted butter, oil, and sugar until combined. Add the eggs and vanilla, whisking to combine. ¼ cup (4 Tbs., 57 g) unsalted butter, ¼ cup (60 ml) canola oil 1 cup (200 g) granulated white sugar 2 large eggs 1 ½ teaspoons vanilla extract
- Add dry ingredients alternately with buttermilk. Add the flour mixture to the creamed mixture alternately with buttermilk, mixing well after each addition. Pour the batter over the top of the pineapple topping. Some of the pineapple slices may still peak above the top of the cake batter. ⅔ cup (160 mL) buttermilk
- Bake. Bake in the center of your preheated 350°F oven for 45 to 50 minutes or until toothpick inserted in center of cake comes out clean (don’t go all the way down or you will just get the brown sugar bottom) . Top of the cake will be a golden brown and spring back when lightly touched. Remove from the oven and allow to cool for 5 minutes in the pan. Use a knife and loosen around the edge of the cake pan, and invert out onto a serving platter. Store leftovers in an airtight container for up to 3 days.
Video
Notes
- Storage: You can store the cake or leftovers in a container, covered, for up to 3 days. Or freeze for up to 3 months. Thaw before serving.
- Pineapple – I used canned pineapple slices, but you can definitely use fresh pineapple if you want. I use pineapple slices and not chunks which might make for a messy topping that doesn’t stay in place. I recommend blotting the pineapple slices dry before starting to remove any extra liquid.
- Cherries – I used jarred maraschino cherries but I think fresh cherries might also work. If they are large I would recommend cutting them in half.
- Cake Flour – I made this cake with cake flour to create a light, fluffy texture. If you don’t have cake flour on hand you can make a Homemade Cake Flour but it won’t be quite the same, or swap and use AP flour (but again the cake might be a bit denser than intended).
- Buttermilk – If you don’t have any buttermilk on hand, you could try making Homemade Buttermilk but it won’t be quite the same as the store-bought but will do in a pinch. But milk and buttermilk are the NOT the same thing and react differently with the baking powder and baking soda, so do not swap in milk.
Has anyone tried using buttermilk powder instead of fresh buttermilk? They always come in large containers and the leftovers get wasted for me
Great question! To avoid waste, you can make your own buttermilk—just mix milk with a little lemon juice or vinegar. Here’s a link with the easy how-to! 😊 https://www.bostongirlbakes.com/make-buttermilk-3-easy-steps/
I can only find low fat buttermilk at my store. Do you think that will be ok?
Yes, low-fat buttermilk should work just fine in this recipe! The slight difference in fat content won’t affect the texture or flavor significantly. Happy baking!