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!!

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!!

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.

Perfect For Easter, Mother’s Day, Spring and Summer Events

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!

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!!

Easy Pineapple Upside Down Cake Base

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 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 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.

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!!

How to Make Pineapple Upside Down Cake

  1. 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.
  2. I used the remaining 3 slices (6 halves) to line the sides of the pan. Nobody likes bald sides.
  3. 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.
  4. 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.

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!!

Inverting The Pineapple Upside Down Cake

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. This is exactly how it looked after inverting.

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

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 it’s 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 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 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.

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!!

Springform Pan Tip

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. Then 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 is a video demonstrating how I make The Best Pineapple Upside Down Cake

 
Favorite Pineapple Dessert Recipes:
The Best Pineapple Upside Down Cake

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

Ingredients

  • 1/2 cup unsalted butter3/4 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

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Recipe originally from March 2014 and reprinted in May 2018

423 comments on “The Best Pineapple Upside Down Cake”

  1. So it’s my turn to make a comment. I tried the recipe today and I have to say, after hunting for the perfect recipe for the past month, I decided to stop right here, because after the reading all the positive reviews, I said to myself, this must be THE ONE! My hubby’s birthday is tomorrow and this is his favourite dessert. Well let’s just say, the cake will not last till tomorrow since it’s already halfway gone. It came out perfect! And this is even though I substituted half of the buttermilk for the pineapple juice and I used mayonnaise instead of sour cream because I didn’t have any. Yes mayo…I use mayo in my chocolate cakes. It’s a magic ingredient that makes it nice and moist. And no, you don’t taste it. Anyway…I have since received two orders for later this month so this is the recipe I will be sticking with. Thanks Averie!

    Rating: 5
    • Thanks for the 5 star review and glad you decided that this was The One for your hubby’s bday tomorrow! I use mayo sometimes in a pinch too. After all it’s really just oil and eggs, can’t hurt in a cake :)

  2. Never done a review for anything before – but this cake is amazing. I’ve made a bunch of different upside down cakes in the past, and this certainly wins the award!

    Rating: 5
  3. Absolutely wonderful. Very moist. I cut down the sugar a bit. I will definitely bake this again

    Rating: 5
  4. My “go-to” pineapple upside down cake! I’ve made this a few times now and I love how delicious it is and how beautiful it looks. This is my husband’s uncle’s favorite type of cake and I make it for his birthday when he’s around. Always a hit!

    Rating: 5
  5. I made this tonight and it was seriously the best pineapple upside-down cake I’ve ever had. We could not get enough of it! Thanks for the recipe and we’ll definitely be making this many more times!

    Rating: 5
  6. I have made this about 10 times now, so I can say with certainty that this recipe is an absolute hit! My father-in-law requests it every year as a Christmas gift, and I make it whenever I am in a pinch and would like to give a homemade treat as a gift. Thank you for the wonderful recipe, Avery!

    Rating: 5
  7. O-M-G!!! This cake is amazing! Love It, really. Thanks for sharing this recipe. 😍 🍍

    Rating: 5
  8. It’s in the oven now, looking and smelling great! Question: could this be made gluten free with a different flour?

  9. Can you use fresh pineapple when making this since you don’t use the juice? Would one be enough?

  10. If I want to make this in an old fashioned ring pan do you think I would double the amount of cake batter? It’s not quite as large as a bundt pan.

  11. This recipe is hands down the best I have ever had. I got a hankering for this cake after a local bakery made little mini versions of these. Their cakes didn’t come close to this one. Thank you for the wonderful recipe!

    Rating: 5
  12. I recently made this dessert for a dinner party of 6. We all agree, it’s the best pineapple upside down cake recipe. I plan to make this again.

  13. I recently made this dessert for a dinner party of 6. We all agree, it’s the best pineapple upside down cake recipe. I plan to make this again.

    Rating: 5
  14. I made this cake yesterday and although it didn’t cook thoroughly it still tastes great after a one minute nuke in the microwave. Do you have any suggestions for high altitude? At 40 minutes the toothpick came out clean but after cooling and inverting the middle was a pudding consistency.

    • I really don’t have expertise with altitude cooking and the adjustments that you’d need to make but there are tons of websites with that type of info if you google it.

      Clearly though if it was pudding-like in the middle it just wasn’t done and I would easily add 10-15 minutes based on your description just as a first guess type of solution. Glad you were able to salvage it though and a quick nuke is working!

  15. I’ve been making pineapple upside down cake for years. Thye are always dense and bread like. I tried this recipe. It was amazing, soft, pineapplely and a big hit!! Thank you for sharing the recipe!

    Rating: 5
  16. Loved the look of the pineapple but the butter/brown sugar mixture seeped out of my springform pan and itis a good one…made a huge smoky mess in my oven! Would make this again in a regular cake pan.

    Rating: 4
  17. Hi I live in Mauritius and zero chance of finding buttermilk! Can i try to make a nut milk / ACV or lemon juice buttermilk alternative or will it ruin it?

    • I would make a real dairy-based version of homemade buttermilk (don’t use nut milk; use actual milk) using lemon juice or ACV and go with that instead. I haven’t personally tried this but that is my guess.

  18. Awesome recipe! We made this and it was amazing!

  19. 5 stars!

    Rating: 5
  20. My entire house loves this cake. Delicious. However, I did run into a problem as I was making it. I used a 9×9 square pan and followed the recipe exactly, but when I poured the batter into the pan it didn’t entirely cover the pineapple and cherries, so I quickly whipped up another batch of batter and poured it on top of the first batch in the cake pan. So my cake was made with two batches of batter and turned out great. I believe I added another 10 minutes bake time.

    Rating: 4
  21. I was looking for a cake recipe for the whole family and I stumbled on this article. I read and followed the instructions carefully and I made it deliciously! Every member of my family is so happy! Thanks for this!

  22. I will be making this for my son. However, I will be using self-rising flour because that is what I have in my house. Can you tell me how to make the necessary changes to the recipe when I use the self-rising flour please? Thanks so much!

    • I have no idea since I’ve never used self-rising flour for this cake and personally, to give some advice, I would not want to try it with a cake that’s as labor-intensive as this one in case you guess incorrectly, and the cake does not turn out.

  23. In all my years of baking, I’ve never made a pineapple upside down cake. Do you drain the pineapple?

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