Homemade Pineapple Upside Down Cake
Homemade pineapple upside-down cake brings that perfect blend of sweet pineapple and a rich, caramelized topping, just like the old-fashioned version grandma used to make. This vintage dessert hasn’t lost its charm over the years—and it’s just as tasty today as it was back then. If you want a show-stopping treat with nostalgic flair, this retro classic is the way to go.
This classic Pineapple Upside Down Cake recipe has been perfected over the years, combining tried-and-true methods with expert tips to make sure you end up with a moist, buttery crumb and beautifully caramelized topping every single time.
| Prep Time | Cook Time | Servings | Prep Level |
|---|---|---|---|
| 20 minutes | 40-45 minutes | 9 | Beginner + |
Ingredient Notes
I’m sharing these ingredients not just so you can make the cake, but so you understand how each one works together to create a dessert that’s rich, flavorful, and irresistibly nostalgic.
Topping
- Butter (melted) forms the rich, golden base that blends with the brown sugar to create that irresistible caramel glaze.
- Brown Sugar is packed with molasses, giving the topping its deep caramel flavor and a hint of smokiness. It melts into a glossy, amber syrup that coats the pineapple like candy.
- Pineapple Slices are sweet, juicy, and slightly tangy; they bring the tropical burst that defines this cake.
- Maraschino Cherries are the bright red pops of color, adding a candy-like sweetness.
Cake
- Softened Butter is creamed into the batter, making sure you end up with a soft crumb and melt-in-your-mouth texture.
- Granulated Sugar helps whip the butter into a fluffy base, giving it a clean, sweet taste that lets the pineapple shine.
- Eggs provide structure and richness. They give the cake a moist interior while contributing to that light golden crust.
- Vanilla Extract helps bring out all the flavors with warm, floral notes.
- All-purpose flour is really the framework of the cake—sifted for airiness—this flour supports the juicy topping without getting soggy.
- Baking Powder is the silent worker that lifts the batter gently, ensuring the cake bakes evenly with a tender rise.
- Salt heightens every flavor, making the sweetness more vivid and the butter more buttery.
- Milk adds moisture and smoothness. It helps balance the batter and create that soft, tender bite you expect from a home-baked cake.
A full printable recipe with measurements and instructions is listed at the bottom of the post on the recipe card.
How To Make Pineapple Upside Down Cake
Topping
Spray an 8-inch by 8-inch baking dish with nonstick cooking spray. Add the brown sugar to the greased baking dish. The sugar will create a brown sugar glaze on the top of the cake after baking. Pour the melted butter over the brown sugar and mix it all together. Spread the butter and sugar mixture over the bottom of the dish.
Next, lay the pineapple slices on top of the brown sugar and butter mixture. Place the cherries in the little spaces in between. You can add as many cherries as you’d like. Typically, you add more pineapples, but mine was small, so I only had a few slices.
Making the Cake
Add the softened butter to a large mixing bowl and cream for about one minute. Add the sugar and cream for about one more minute. Plop in the eggs, one at a time, and mix them into the batter. Next, add the vanilla extract. Then, measure out your baking powder and prepare it to add to the flour.
Next, add the flour, salt, and baking powder to a sifter. Sift the ingredients into the bowl. Sifting the flour will add a light, fluffy texture to your cake. Mix the flour mixture into the batter. Pour the milk into the batter and mix it together.
Pour the batter on top of the pineapple and spread it out evenly. I baked it in my 8″ x 8″ dish. It did make it a thicker cake in the smaller dish, which was delish!
Bake for approximately 40-45 minutes or until a cake tester comes out clean. If the cake is not done, extend the baking time for a few minutes at a time.
Allow the cake to cool, and invert it onto a plate or cookie sheet. It helps to scrape the sides with a knife before inverting so the cake doesn’t stick.
Julie’s Tips For Success
- I used an 8-inch by 8-inch baking dish for the recipe because my pineapple was small. If you use more pineapple, you can use a larger cake pan. However, your cake will not be as thick. I used a ceramic baking dish, but you can also use a heavy skillet, such as a 10-inch cast-iron skillet, for the recipe. The cooking time is the same in a skillet or a baking dish.
- Grease the pan thoroughly before adding the pineapple and cherries; otherwise, the cake may stick to the pan and be difficult to remove.
- If you used canned pineapple, be sure to drain the pineapple juice before removing the pineapple slices. Dry the pineapple slices with a paper towel before adding them to the baking dish.
- Make sure you don’t over-mix the batter; otherwise, it might turn out dry and dense. You want it to be a moist cake. If your cake comes out dry, add a few tablespoons of the leftover pineapple juice to the batter.
- Use a cake tester to check the center of the cake for doneness. If it’s still a bit wet, bake it a few more minutes. If the top is getting a little bit brown, you can place some aluminum foil over the top while it finishes baking to keep the top from getting too brown.
- Pineapple slices have a lot of juice, so you need to dry them off before adding them to the baking dish. Grab a paper towel and pat the slices dry. This will help keep your cake from getting too soggy.
- You can use fresh or canned pineapple for the recipe.
Leftovers and Storage
You will need to refrigerate the cake, but make sure it is in an airtight container or covered with some plastic wrap. It is good for about three days, and then the cake will start to get wet from the pineapple juice.
You can freeze an upside-down pineapple cake. Allow the cake to cool to room temperature, wrap it in plastic wrap, and store it in an airtight container. The cake can be frozen for up to three months. When you’re ready to serve it, place it in the refrigerator to thaw overnight. Having said that, it won’t taste as good as a freshly baked cake.
Substitutions and Variations
- If you are using fresh pineapple, you will need about seven slices.
- Swap out the pineapple for another fruit that is in season, such as peaches or pears.
- Add some cinnamon and nutmeg to the topping for a more fall feel.
- Using a yellow cake mix, such as Betty Crocker, can help you make the recipe faster.
Make Ahead Or Not
You can make part of the cake ahead of time. Wait to add the brown sugar and pineapple layer until you are ready to bake the cake. You can mix the cake portion a day ahead, but leave it in the mixing bowl, cover it with plastic wrap, and keep it refrigerated. When you are ready to bake it, let the cake batter come to room temperature before adding it to the baking dish.
More Delicious Pineapple Recipes
If you love pineapples, you will love these recipes.
- That no-bake pineapple lush dessert is perfect when you’re craving something cool and creamy without turning on the oven.
- If you’re not sure how to grill pineapple, it’s easier than you think and adds such a smoky-sweet flavor.
- This no-bake pineapple pie recipe is ideal for summer gatherings when you need a quick and tropical treat.
- Using cake mix makes this pineapple upside down cake recipe so much simpler without skimping on the classic flavor.
Homemade Pineapple Upside Down Cake
Ingredients
Topping
- 1/4 cup butter melted
- 1/2 cup brown sugar
- 20 ounce can pineapple slices or fresh pineapple – you will need 7 slices
- Handful of pitted maraschino cherries
Cake
- 1/2 cup butter softened
- 3/4 cup sugar
- 2 eggs
- 1 teaspoon vanilla extract
- 1-1/2 cups all-purpose flour sifted
- 1-1/2 teaspoons baking powder
- 1/4 teaspoon salt
- 1/2 cup milk
Instructions
- Preheat oven to 350-degrees.
- Grease a 8-inch x 8-inch baking dish.
Topping
- Add the brown sugar to the bottom of the pan.
- Melt butter, pour over the top of the brown sugar, mix together, and spread over the entire dish.
- Place the pineapples and cherries on top of the brown sugar. (I like to place cherry in the center of each pineapple slice).
Cake
- Start by adding the butter to a large bowl and cream for one minute.
- Add the sugar and cream again for one more minute.
- Add the eggs, one at a time, and mix together.
- Add the vanilla and mix together.
- Combine flour, salt, and baking powder. Sift into the bowl and mix.
- Add the milk, mix together, and gently pour cake batter over pineapple.
- Bake for 40-45 minutes or until a cake tester comes out clean.
- Let the cake cool to room temperature. Run a knife around the edges to loosen the cake.
- To flip the cake, place a large serving plate over the top of the cake. Hold the plate and pan tightly together with both hands (use oven mitts if it’s still warm), then flip it in one smooth motion. Leave the pan over the cake for a minute to let all the syrup and pineapple release.
Notes
Nutrition
If I was using canned pineapple, how much would I use? You said you normally use more than shown, so more than one layer of pineapple?
@Barbara, in a 9×13 I squeezed 12 slices in. Which is a little less than a can and a half.
@April Walker, I am baking this today,and i have been making this same cake for 58 years.I always use my round,black cast iron skillet for this.I know not everyone may have a skillet like this,so then 9×13 would be next.I love the way the glaze comes out when done ,cooled for a few mins.and flipped out of the skillet.My mother and grandmother made them the same way i do.I use one reg. size can of pineapple,and i use it all except 3 slices ,when using my skillet.I also substitute the drained pineapple juice from the can of pineapple ,instead of milk.Everything else is the same .joyce p.
@joyce phillips, if using cast iron skillet what size and do you double it. I have 3 different sized cast pans. Do i double the recipe for cast iron pan. I read alot of people stated double the ingredients and some stated it was dry. bake for 40 min only. Any tips would be great.
@Julie, I just made it according to the recipe and it worked perfectly in my 10” cast iron skillet. Definitely done at 40 min. Haven’t eaten it yet though so idk if it’s dry. I will def sub the milk for pineapple juice if I make it again
Sounds SO good! Thanks for sharing!
Hi Barbara!
I think a 20 oz. can of sliced pineapple would be plenty. (I’ll add that to my recipe – thank you for asking:)
I used one layer of pineapple on my cake. Sometimes people overlap them a little, but you can just lay them next to each other. It also depends on the size of pan that you’re using.
If you use an 8″ x 8″ baking dish, you will only need about five or six slices, but if you use a larger dish like a 9″ x 13″, you might use about 10 slices. So, a 20 oz. can will be plenty.
Hope that helps! Have a good day!
I love pineapple upside down cake! Looks so pretty and delicious! PINNED!
Thanks, Kelly!
We love a pineapple upside down cake, this looks so delicious! Hope you are having a wonderful week and thanks so much for posting with Full Plate Thursday!
Miz Helen
Thanks Miz Helen! Hope you’re having a great week, too!
I tried this recipe. I followed it exactly. So I understand you used an 8×8 pan but when using a 9×13 the ingredients need to be doubled and altered because I ended up with a cake about 2 inches in height! This was the flattest cake I have ever made. I guess this is how it is supposed to look. I looked up other pictures and it is pretty flat looking. I just didn’t like it that way.
Hi Elle, I think that’s the nature of pineapple upside down cakes. You could make two of them in two round pans and stack them after cooking and cooling off and you would have a taller cake. It would be neat to have the pineapple at the bottom and in the middle.
My cake came out dry. Would have liked a moister cake.
Hi SMT, I am sorry to hear that.
@SMT, I added a little of the leftover pineapple juice to my cake, just a few tablespoons!! Hope that helps
Great recipe, thank you. I’ve doubled the recipe for a 9×13″ glass dish and added ~0.5 cup of crushed pineapple to the batter. The cake raised well and was light and moist. Definitely a keeper 🙂
Hi Irina,
You’re welcome and that’s great to hear! Thanks for stopping by and sharing!
@Irina,
Thank for the tip! I can’t wait to make this recipe tonight.
Thanks Julie
@Amanda, I always use the saved juice to add in place of half of the milk..
Crushed pineapple sounds even better!!!! 👍
This is the easiest recipe ever. This recipe had a great homemade taste. I gave only 4 stars because the batter wasn’t enough for a larger cake.
I made this recipe and it came out moist and delicious. Will definitely make again.
That’s great to hear! Thanks for sharing!
I double recipe for a 9×13. I also add crushed pineapple to the batter as well as some of the juice, in addition to the milk. Comes out perfectly every time! My family loves it and it’s also one of my go tos for work potlucks!
I doubled the recipe and used a 9×13 pan, one can of pineapple was still plenty. The cake batter seemed really thick, but I just followed the recipe exactly and it turned out great. My cake did take around 1 hour to bake. This cake is so good!
So, I decided I wanted to make this cake in a Bundt pan. I cooked it for a longer time (I think about 15 minutes) until the toothpick came out clean. When I turned it out, it was beautiful, moist and delicious. I will admit, I used more butter and brown sugar for the glaze because it was a bigger cake. Wowza! It sure was a hit!
I’ve made this cake 5 times now and it’s always delicious. Pineapples were on sale and this recipe compliments fresh pinnapple perfectly.
I love to hear that! It’s wonderful when they are on sale.
I’m on my 4th attempt with this cake. Baking for someone in hospital, wanting disposable pan. I’ve learned that aluminum disposable pans are not a good idea for this cake. Using glass now, hoping it won’t be a 4th throwaway. I suspect the cake is delicious, if only I could get it right! I’ve made cakes my entire life, nothing as challenging as an upside down pineapple cake though. It should be easy, I know. thanks for sharing the recipe.
Hi Nora,
How’d it go? You’re right to make it in a glass pan and then transferring it over to a disposable pan to take to the hospital. I bet they will love it!
I made this today, and it was amazing. I’ve never enjoyed the really soggy ones I’ve had, blotting the juice from the pineapples made all the difference! Thank you!
Awesome! So glad you loved it. Thanks for stopping by to share – that makes my day!
This was so nostalgic and amazing. I did not realize I was out of milk until I started so I used 1/2 cup heavy cream and a bit of buttermilk to thin it and it was delicious. I cooked it in the cast iron skillet and it got a bit crunchy and caramelized and it was terrific! As info, if anyone is using the cast iron skillet, the cooking time was the same, 40 minutes.
I used a 20 ounce can of crushed pineapple and squeezed the juice out of it. It was a good amount.
Thanks for the awesome recipe!! I am going to add this to brunch!
Thank you for this! The crunchy sounds amazing! I’m so glad you loved it.
I actually have a question. What if you don’t have maraschino cherries can you use candied ones instead
Hi Mary,
I haven’t used candied cherries, so I am not sure. But, it might be delicious!
I have made it this is the first time so happy to have made it now we wait and see
Hi Mary,
I hope you love it!
Hi! I stumbled across this recipe trying to find something last minute to make for dinner guests. I love when I almost have everything needed to make a dish.
It was super easy to put together and I love the fact the cake is entirely homemade. My only issue, aside from being completely intimidated by pineapple upside-down, is that my cake batter came out very thick. Fingers crossed it still works, but what consistency should my batter be? Should I have added more liquid?
This is my first time making a cake from scratch, and it is something I will do again, I just need to figure out this consistency.
Thank you for any help!
Hi Jessica,
It should be fine. You can check it with a cake tester or a sharp knife to see if it’s done. You might need to cook it a few minutes longer. I hope you all love it!
I had heart bypass surgery about 2 months ago, so have to lower my salt and saturated fat. I used unsalted butter in the topping. I made several substitutions in the batter. I used brown sugar for more richness. I used sodium free baking powder. Left the salt out. Replaced the milk with pineapple juice. Used slightly less avocado oil in place of the butter. I also had no cherries or
Pineapple slices so I used the well drained crushed pineapple and walnut pieces and slivered almonds instead.
Sounds like a great alternative! And delicious! Thank you for sharing that and hope you’re on the mend. 🙂
I made this and followed the recipe exactly and it came out perfectly. It was the most delicious cake I have ever baked! My husband loved it too.
That’s awesome! I am so glad to hear that. Thank you for sharing!
Can you use lactose free milk??
Hi Roe,
I am not sure. I haven’t used it before with this recipe.
Tastes fine but way to heavy of a cake for my liking
I would like to double this cake for a thick 9×13. I have made it in a 8×8 pan and it turned out perfectly.
How long would it take to bake at 350° if I were to double the recipe?
I haven’t doubled the recipe, so I am not sure. But, I would check it at the 45 minute mark and use a cake tester or toothpick and if it comes out with batter still on it, you might need to cook 10 more minutes. Keep checking after 5 to 10 minute increments. Hope that helps! Let us know what the final time is.
In your tips,,,it said to make sure you grease your pan.
The #2 step with the brown sugar and butter say mix together in bottom of pan?
Whyyyy do we need to geease the pan if we are mixing the brown sugar mixture in bottom??
Great question! I don’t like anything sticking to my pans, because it makes clean up easier. You might be able to get away with not greasing the pan, but the brown sugar will stick to the pan easily. If you don’t do it on the bottom, I would definitely do it on the sides.
loves the easy receipes quite easy .an they came out good added a few things but other wise they are awesome..will make again
So glad you liked it!