The Best Pineapple Upside Down Cake

The Best Pineapple Upside-Down Cake — So soft, moist, and really is the best!! A cheery, happy cake that’s sure to put a smile on anyone’s face! This 100% from-scratch cake is an EASY reader favorite you’re going to love!!

best Pineapple Upside-Down Cake

Homemade Pineapple Upside Down Cake

My 7-year-old had never had pineapple upside down cake and she loves pineapple. Whoa. How did that happen?

So I decided to get busy and make a homemade pineapple upside down cake. It turned out to be the best pineapple upside-down cake I’ve ever had, and one of the best cakes I’ve ever put to my lips.

I think it would be a perfect cake for Easter, Mother’s Day, baby and bridal showers, brunch, or anytime you want a cheery, sunny, happy cake!

It’s an easy cake to make, and you don’t even a mixer. For the cake base, I adapted my favorite buttermilk coffee cake that I’ve used for so many cakes, including my Blueberry Muffin and Buttermilk Pancakes CakeCranberry White Chocolate Chip Bliss CakePeaches and Cream Fluffy Muffin CakeCream Cheese-Swirled Cherry and Mixed Berries Cake, and more.

I love this cake base because it’s fast and easy to make, and the cakes always turn out supremely moist, springy, and fluffy thanks to the buttermilk, sour cream, and oil. That trifecta of moisturizing and tenderizing ingredients makes it impossible to have a dry cake.

Not to mention, the buttery, brown sugary pineapple juice that seeps down into the cake from the slices on top make the cake so soft, moist, and buttery that it just melts in your mouth.

slice of homemade Pineapple Upside-Down Cake

The cake is soft, sweet, with an almost imperceptible tang from the buttermilk that adds another layer of flavor. The pineapple slices add chewiness and texture to the otherwise falling-apart-soft crumb.

While baking, the pineapple caramelizes in a butter and brown sugar bath, giving the pineapple upside down cake its signature glistening top and adding so much rich, browned butter flavor to the pineapple.

There’s no better way to get your Vitamin C than via pineapple baked in it’s own brown sugar-browned butter sauce.

The maraschino cherries add a burst of sweet flavor, and they’re so eye-catching on the cake. And my daughter loves cherries.

It feels great to make nostalgic and classic recipes, and between how this pineapple upside down cake looked and how it tasted, it just made me so happy.

easy Pineapple Upside-Down Cake sliced on white platter

Pineapple Upside Down Cake Ingredients

To make this easy pineapple upside down cake, you’ll need the following ingredients: 

  • Unsalted butter
  • Light brown sugar
  • Canned pineapple slices
  • Maraschino cherries
  • All-purpose flour
  • Granulated sugar
  • Baking powder
  • Egg
  • Buttermilk
  • Sour cream
  • Canola oil
  • Vanilla extract

You must use each of these ingredients as they’re listed. Substitutions like whole wheat flour or an alternative sweetener may result in a less than stellar upside down cake. 

how to make Pineapple Upside-Down Cake

How to Make Pineapple Upside Down Cake

I used one 20-ounce can pineapple slices. I kept one slice whole for the center of the cake, and then fanned 12 halves around it. My pet peeve about most pineapple upside-down cakes is that there’s not enough pineapple if you keep the rings whole and intact. The focus of a pineapple upside-down cake should be on the pineapple, so I tried to maximize the pineapple coverage on top by using a fanning technique.

I used the remaining 3 slices (6 halves) to line the sides of the pan. Nobody likes bald sides.

After getting the pineapple and cherries in the pan, whisk together the cake batter and turn it out into the pan. I filled my 9-inch round cake pan about 3/4-inch full with batter.

Although the cake doesn’t rise a ton, it’s still a cake and rises some, so don’t exceed about 3/4-full, the same idea as when filling a muffin tin. Discard the last bit of batter if need be. I mention this because all cake pans, the exact amount of pineapple, cherries, etc will vary slightly.

I made the cake before bed and let it cool overnight in the pan with a sheet of foil over it. There’s no big rush to get it out of the pan. And honestly, inverting cakes gives me sweaty palms every time and I was stalling.

But because of how buttery the topping is, the pan is so well-greased that the cake just plopped right out. Not even one slice of pineapple or cherry out of order. 

baked Pineapple Upside-Down Cake ready to be inverted

Can I Make This With Fresh Pineapple? 

I’ve only ever made this cake as written, so I can’t say for sure whether fresh pineapple would work in place of canned. Most likely yes, but please let me know if you try this and it works out! 

Can I Make This in a Regular 9-Inch Cake Pan?

No, regular round cake pans aren’t deep enough. You also can’t use a 9-inch square baking pan for this. You have to use a 9-inch round springform pan, otherwise this homemade pineapple upside down cake recipe won’t turn out right. 

Pineapple Upside-Down Cake from scratch on platter

Can I Use Pineapple Juice in Place of the Buttermilk? 

No, you need real buttermilk to help this cake rise properly. You can use the leftover pineapple juice in the can in cocktails, smoothies, and more though! 

Is There a Buttermilk Substitute I Can Use? 

If possible, get your hands on real buttermilk. If that’s not possible, you can try making a buttermilk substitute (for every 1 cup of milk, mix in 1 tablespoon lemon juice or white vinegar). If you have to make a buttermilk substitute, you should use 2% or whole milk for the best results.  

Pineapple Upside-Down Cake recipe

Can I Turn This Cake Into Cupcakes? 

I haven’t tried that before because I just don’t have the patience for it! So unfortunately I can’t tell you if this pineapple upside down cake from scratch can be made as cupcakes. 

Can I Turn This Into a Layer Cake?

I don’t think layering pineapple upside down cake is a good idea. This cake is incredibly moist and heavy, and I think if you tried to make two layers and stack them on top of each other the entire cake would fall apart. 

slice of homemade Pineapple Upside-Down Cake

Tips for the Best Pineapple Upside Down Cake

Make sure you are using a good quality springform pan that you know is reliable. From time to time, people write to me saying their springform pan leaked, butter went all over, and they get upset with me. This is not my fault, peeps. It’s your pan that leaked. The solution?

Test your pan with water in it.

Does it leak? If so, it will probably leak with the melted butter in it. Don’t make the cake until you have a pan you trust, simple as that.

This is the 9-inch springform pan I currently use and I have never had it leak with this cake. I have, however, had it leak when I quickly (and I was half asleep) put it together and sealed the latch carelessly. I do recommend it and it’s been a workhorse with other cakes over the years. I bought it in 2015 and it still looks and works as good as new.

The Best Pineapple Upside-Down Cake - So soft, moist, and really is The Best!! A cheery, happy cake that's sure to put a smile on anyone's face! This 100% from-scratch cake is an EASY reader favorite you're going to love!!

The Best Pineapple Upside-Down Cake - So soft, moist, and really is The Best!! A cheery, happy cake that's sure to put a smile on anyone's face! This 100% from-scratch cake is an EASY reader favorite you're going to love!!

Here’s a video demonstrating how to make pineapple upside down cake:

The Best Pineapple Upside Down Cake

The Best Pineapple Upside Down Cake

This pineapple upside down cake is so soft, moist, and really is the best!! A cheery, happy cake that’s sure to put a smile on anyone’s face! This 100% from-scratch cake is an EASY reader favorite you’re going to love!!

Prep Time 15 minutes
Cook Time 40 minutes
Additional Time 35 minutes
Total Time 1 hour 30 minutes

Ingredients

  • 1/2 cup unsalted butter
  • 3/4 cup light brown sugar, packed
  • one 20-ounce can pineapple slices
  • about 12 maraschino cherries
  • 1 cup all-purpose flour
  • 3/4 cup granulated sugar
  • 2 teaspoons baking powder
  • pinch salt, optional and to taste
  • 1 large egg
  • 1/2 cup buttermilk (or Powdered Buttermilk, use 2 tablespoons with the dry ingredients + 1/2 cup water added with the wet)
  • 1/3 cup sour cream, lite is okay (plain Greek yogurt may be substituted)
  • 3 tablespoons canola or vegetable oil
  • 2 teaspoons vanilla extract

Instructions

  1. Preheat oven to 350F.
  2. In a small, microwave-safe bowl, melt the butter, about 1 minute on high power.
  3. Pour the butter into a 9-inch springform cake pan. Use your finger to run a bit of butter around the side of the pan so it’s well-greased.
  4. Evenly sprinkle the brown sugar over the butter.
  5. Add 1 whole pineapple slice to the center of the pan.
  6. Halve the remaining slices vertically. Stagger them in a fan-like fashion going around the cake. I used 12 slices.
  7. Place the remaining slices around the sides of the cake pan with the curved side pointing down toward the bottom of the pan (see photos for reference). There will likely be bare side patches with no pineapple coverage, that’s okay.
  8. Place 1 cherry in the center of the whole pineapple slice in the middle of the pan.
  9. Place 1 cherry in the center cutout of all the fanned pineapple slices; set pan aside.
  10. In a large bowl, whisk together flour, granulated sugar, baking powder, optional salt; set aside.
  11. In a separate small bowl, whisk together the next 5 wet ingredients (through vanilla).
  12. Add the wet mixture to the dry, mixing lightly with a spoon or folding with a spatula until just combined. Small lumps will be present, don’t overmix or try to stir them smooth.
  13. Gently turn batter out into prepared pan, being careful to not disturb the pineapple slices on the sides or bottom. Fill pan only to about 3/4-full. If you have a little extra batter, discard it rather than overfilling your pan.
  14. Place pan on a cookie sheet (to catch anything that does overflow) and bake for about 40 minutes, or until center is set and not jiggly, and a toothpick inserted in the center comes out clean or with a few moist crumbs, but no batter. Only go down about 1-inch with the toothpick, not all the way to the bottom where you’ll hit gooey pineapple juice.
  15. Place pan on a wire rack and allow cake to cool for at least 30 minutes before inverting, slicing, and serving. I allowed cake to cool overnight, covered with a sheet of foil, before inverting. Cake will keep airtight at room temperature for up to 5 days.

Cake base adapted from Blueberry Muffin and Buttermilk Pancakes Cake


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Nutrition Information:

Yield:

10

Serving Size:

1

Amount Per Serving: Calories: 299 Total Fat: 7g Saturated Fat: 1g Trans Fat: 0g Unsaturated Fat: 4g Cholesterol: 26mg Sodium: 172mg Carbohydrates: 56g Fiber: 1g Sugar: 44g Protein: 6g

More Easy Pineapple Recipes: 

 Pineapple Banana & Coconut Cream Smoothie (vegan, GF) – Tastes like a virgin pina colada. Sweet, creamy, refreshing & healthy. No need to add sugar since the fruit is sweet enough.

Pineapple Coconut Oil Banana Bread — Banana bread spiked with pineapple and coconut oil that’s so good!

Pineapple Poke Cake With Pineapple Glaze — A pineapple version of a poke cake with a pineapple glaze that you’ll adore!

Tropical Escape Pineapple Crumble Bars — Soft, tender bars that have a great crumble topping that will remind you of the tropics!

Angel Pineapple Lush Parfaits — This is a 4-ingredient, no-bake dessert that’s ridiculously easy, you don’t need a mixer, and you don’t have to turn your oven on.

Mango Pineapple Frozen Margaritas — They’re fruity and sweet but not too sweet, and they pack a punch. There’s no margarita mix, no added refined sugar, and the sweetness comes naturally from the fruit and agave.

Recipe originally from March 2014 and reprinted in May 2018

461 comments on “The Best Pineapple Upside Down Cake”

  1. I am so making this cake ! could i omit the oil the recipe calls for and use a substitute of any other type ?

    • Can I use pineapple juice to replace the buttermilk? If so would it still be the same amount – 1/2 cup? If can do this – would the rest of the ingredients and directions stay the same?

      • I really don’t know. I have only made it as written and don’t know what will happen if you change things up.

      • Yes you can I’ve made it like that same amount & add a splash of Lemon Juice or Apple Cider Vinegar any acid it interacts with the Baking Powder & makes it rise more.Makes it fluffier too.

    • Yes you can use Applesauce & mayo for the eggs 1 dollop size like an egg.Also really simple get a box of yellow cake mix follow instructions for the pineapple upside down part then follow directions on box of cake mix.It’s the easiest way.If you google what to substitute in recipes that will help you out.I’ve made this before both this recipe & different variations.Also you can use other fruits I’ve even used Fruit Cocktail get the Sugar Free drain the juice b/c to me it’s way too sweet if you get the Fruit cocktail in heavy syrup.I’ve also added Cinnamon,Nutmeg,& Ginger to the batter really good.Sprinkle in to your desired taste do this before adding the eggs to taste the batter to make sure it’s up to your liking.

  2. Do you Add the water as the Recipe shows? The video does not have the water added. Thank you.

  3. I double the butter and sugar and use a 12″ cast iron skillet. The “glaze” almost goes through the entire cake somehow and my cake is taller. I also make a vanilla-nutmeg sauce to go over the cake. Talk about food porn.

    • How did it come out ? I had used a 10″ pan but it is not spring form pan 😭 I have it in the oven now

      • Hi
        I wanted to know if there’s a fair portion of cake because in the picture up top it looks like very little cake and more toppings. I would like to make it for thanksgiving but I want to make sure it’s enough cake, because dealing with my family they criticize everything. Help

      • The cake itself is not a ‘tall’ cake. It would depend on how many people you’re serving. If you have more than 8-10 then you’d want to also make another dessert is my rec.

  4. If my springform pan leaks with water inside it, can I solve this with aluminum foil or parchment paper?

    • I guess it would depend on how bad it’s leaking and your ability to not care if you go to the work of making the cake and then if your pan failed on you, would you be okay with that? I would be livid. I would personally buy a new pan before going to the work of making the cake so I was sure it would turn out.

  5. WOW !! I made it yesterday for my 4th of July celebration and my guests kept coming back for more !! What a DELICIOUS cake, I can’t wait to make again !!! I MEAN THAT ! Thanks again for yet another grade A recipe from you !

  6. I tried this recipe with quite a few modifications and it turned out quite nicely. I made it gluten free. I substituted the regular flour with gluten free self raising flour.I used fresh pineapple instead of cannedI didnt have a springform tin that didnt leak, so i used a silicone cake tin instead.it was a very nice recipe thank you. if i had followed everything 100% im sure it would have been beyond perfect

    Rating: 5
  7. Thank you for this lovely cake……It is so good. My whole family loves Pineapple Upside Down Cake and this one is a big hit.The only changed I made was to put 3 TBSP of Caramel Sauce over the Pineapple before I put the batter on. It is very good with the Caramel too.

    Rating: 5
  8. Thank you for your reply……Your cake is just beautiful, I have never seen one so lovely… It not only looks great but taste even better, it is so good.

    Rating: 5
  9. Can I use a 12 inch springform pan?

  10. I am not a great baker but love pineapple upside down cake! This above all other recipes feels right so I will try it!

  11. Hi
    I just finished making this cake and I had a couple issues, but both isn’t in regards to the recipe. First, my brand new springform pan was leaking some of the butter but I add a little more so hopefully it won’t affect the cake. Secondly, after mixing the wet to the dry my batter wasn’t as loose as yours so I don’t know what went wrong. Do anyone have any advice just in case I have to do it over.

    • Leaking springform – buy a new one. They are prone to leaking and some are just worse than others. It can take a few to find one that works for you.

      A batter not as loose – possibly too much flour/heavyhanded when measuring the flour, I would cut back a smidge.

  12. I made this for the first time and it was amazing!! So light And fluffy. Great taste.

    Rating: 5
  13. This was really easy to make and turned out beautifully! I made it for Thanksgiving and my family ate the whole cake that night! They asked me to make another one today, thank you for the awesome recipe!

    Rating: 5
  14. This cake is very good. I did not have buttermilk. I substituted 1/4 pineapple juice from the canned pineapple, mixed with whole mile and a 1/2 tsp of vinegar which = 1/2 buttermilk. There was way too much butter so next time I will use 1/2 stick (1/4 cup) melted. Thanks for a good recipe.

    Rating: 4

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