Classic Pineapple Upside-Down Cake

4.92 from 37 votes
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Classic pineapple upside-down cake made from scratch with ease. A tender vanilla cake topped caramelized brown sugar, Maraschino cherries, walnuts, and pineapple rings. Impress your loved ones with this stunning dessert!

Pineapple upside-down cake with cherries and walnuts

Pineapple upside down cake is nostalgic and full of flair. No frosting needed for this timeless sweet treat. Fruit and nuts are baked right into a stunning caramelized topping. The cake has three components; brown sugar schmear, pineapple cherry decoration, and a thick and buttery vanilla batter. It’s a trifecta of flavors that don’t go out of style.

It’s our family tradition to make this cake for birthday celebrations. My husbands Grandma Rose used to whip this together as a special treat. A big warm slice always puts a smile on his face. I made sure to include it in my cookbook, Easy Culinary Science for Better Cooking so that our children master the recipe and make it for us someday!

spatula spreading a brown sugar and butter schmear to the bottom of a cake pan

How to make pineapple upside down cake

  • Mix butter, honey, brown sugar, and vanilla.
  • Spread created schmear on the bottom of a greased cake pan.
  • Arrange pineapple rings, cherries, and walnuts.
  • Cream butter and sugar. Mix in vanilla, eggs, and milk.
  • Gradually add in sifted flour and baking powder.
  • Pour cake batter into the pan, and spread out evenly.
  • Bake until cake is golden brown, 30 to 40 minutes.
  • Cool for 45 to 60 minutes until warm.
  • Invert cake onto a plate, wait 5 minutes, then remove pan.

What size cake pan do you use?

I use a tall 8½ X 2½-inch pan, or 9-inch round cake pan that’s at least 2-inches deep. The size allows for the layers of fruit and batter to rise and expand. The cake bakes up tall but shrinks a little in size once flipped over due to the weight of the topping.

person adding cherries to the center of a pineapple ring inside a cake pan

How do you make the caramel topping?

The bottom of the pan is layered with a buttery brown sugar schmear, and if you like, add a ½ teaspoon of rum to the topping. Most recipes call for melted butter and sugar, but I find that whipping sugar with softened butter makes it easier to spread and it has a more even coating when baked. As the cake bakes the sugars begin to caramelize around 320°F (160°C).

How do you make the fruit design on the cake?

Use canned pineapple rings or fresh ripened can also be easily cut and cored with a round cutter. Typically seven pieces can fit on top. Place two drained maraschino cherries in the center of each ring. Add chopped walnuts into all of the nooks and crannies not occupied by fruit, around the perimeter and in between. Other types of fruit like peach, pear, apple, strawberry, or mango can be substituted.

spatula spreading cake batter over pineapple rings and chopped walnuts

What technique do you use to make the cake?

The classic creaming technique works the best. It provides a strong, nicely risen cake that’s able to hold the weight of the topping. Creaming cool butter and sugar helps with the rise because the sugar creates mini pockets of air in the butter which fill with carbon dioxide as the baking powder reacts with the milk. Science! The gas expands in size to make the cake rise and gets trapped by the fat and gluten protein network in the batter as it cooks.

Does butter temperature matter when making a cake?

Yes! To maximize cake rise, use cool butter between 60-65°F (16-18°C) for creaming with the sugar. The fat crystals at this range are able to aerate the butter and trap it inside the batter. Too cold and air cannot get whipped in, too warm and the butter will not hold the air.

An instant-read thermometer works best to check the temperature, or it should feel cool to the touch and slightly dent when pressed. It will take 30 to 60 minutes to soften when left on the counter from the refrigerator.

baked vanilla cake in a pan cooling on a wire rack

What kind of flour do you use for a tender cake?

Cake flour is used because of its lower protein content. It reduces gluten formation, to achieve a tender crumb while preventing a rubbery texture.

How do you unmold the cake so that the topping stays in place?

Flip the cake when it’s warm but not hot, this gives the topping time to set the caramel and fruit together. Don’t wait until it’s completely cool or everything will stick to the bottom of the pan. Place a plate on top of the cake pan, then swiftly invert.

Let the cake sit for about 5 minutes before lifting up the pan. This allows any stuck bits to gradually release onto the surface. See that caramel ring on the edges and tender baked fruit that’s just snuggling with the cake? Yep, the perfect marriage of sweet, fruity and tender pieces of heaven.

close up of a cake with pineapple rings with cherries in the middle

More Sweets recipes

What’s the benefit of using cake flour vs. all-purpose flour?

One of the key differences in types of flour is the amount of protein. The more protein, the higher the gluten-forming potential, which contributes to volume, texture, structure, and appearance. Cake flour contains between 6-8% protein versus all-purpose which has 10-13%. This can make a big difference in the texture of the baked cake. (Source: On Baking: A Textbook of Culinary Fundamentals)

Classic Pineapple Upside-Down Cake

Classic pineapple upside-down cake made from scratch. Tender vanilla cake topped caramelized brown sugar, Maraschino cherries, walnuts, and pineapple rings.
4.92 from 37 votes
Prep Time30 minutes
Cook Time35 minutes
Total Time1 hour 5 minutes
Servings 8 servings
Course Dessert
Cuisine American



  • ½ cup unsalted butter, softened to room temperature
  • 4 ½ teaspoons honey
  • 1 cup dark brown sugar, packed
  • ¼ teaspoon pure vanilla extract
  • 7 pieces pineapple rings, canned, 3-inches wide
  • 14 maraschino cherries, drained
  • ¼ cup walnuts, chopped


  • 1 ⅓ cups cake flour
  • 2 teaspoons double-acting baking powder
  • ½ cup unsalted butter, softened, 60 to 65°F (16 to 18°C)
  • ½ cup granulated sugar, plus 2 more tablespoons
  • ½ teaspoon pure vanilla extract
  • 2 large eggs, room temperature
  • 4 teaspoons whole milk, room temperature


  • Adjust oven rack to middle position and preheat to 350°F (177°C).


  • Use a handheld mixer or stand mixer fitted with a paddle to combine butter, honey, brown sugar, and vanilla over medium speed in a bowl, 30 seconds.
  • Lightly grease the bottom and sides of an 8 1⁄2 x 2 1⁄2-inch or 9 x 2-inch round cake pan with vegetable oil.
  • Evenly spread brown sugar mixture over the bottom of the pan.
  • Place one of the pineapple rings in the middle and 6 around the edges.
  • Add two cherries in the center of each pineapple ring.
  • Add walnuts to the edges where the brown sugar mixture is exposed and add small broken pieces in the center between the rings.


  • Sift flour and baking powder in a medium-size bowl. Whisk to combine.
  • In a separate medium-sized bowl, add softened butter and granulated sugar. Using the paddle attachment, mix on low speed until just combined, 20 seconds. Increase speed to medium and mix for 3 minutes until the mixture is light and creamy. Scrape down the sides as needed.
  • Add vanilla and mix on medium speed for 10 seconds. 
  • Add eggs one at a time, on medium speed until creamy, 30 seconds. Scrape the bowl and repeat with the second egg.
  • Add milk and combine on medium speed, 15 seconds.
  • On low speed add flour mixture in 3 batches, mixing until just combined, 10 seconds each interval. Scrape sides as needed. Pour batter into the pan over the pineapples; it will be thick. Use a spatula to spread evenly.
  • Bake until cake is golden brown, springs back when touched and a toothpick inserted in the center comes out clean with a few crumbs attached, or center of the cake registers about 185-190°F (85-88°C), about 30 to 40 minutes. The bake time will depend on the size of your pan.
  • Allow cake to cool in the pan on a cooling rack for 45 to 60 minutes. The cake will still be slightly warm but will set as it continues to cook in the pan. Do not cool completely or the topping will stick to the bottom.
  • Run a knife around the edges of the cake, invert onto a serving platter, and then wait 5 minutes before lifting off the pan. Serve warm.


  • Leftover cake can be stored at room temperature in an airtight container for 1 day.
  • Optional: Add in ½ teaspoon of rum to brown sugar and butter schmear for extra flavor!

Nutrition Facts

Serves: 8 servings
Calories 491kcal (25%)Carbohydrates 59g (20%)Protein 2g (4%)Fat 28g (43%)Saturated Fat 15g (75%)Polyunsaturated Fat 4gMonounsaturated Fat 1gCholesterol 63mg (21%)Sodium 137mg (6%)Potassium 5mgFiber 1g (4%)Sugar 45g (50%)Vitamin A 850IU (17%)Vitamin C 8.3mg (10%)Calcium 90mg (9%)Iron 1.4mg (8%)

Percent Daily Values are based on a 2000-calorie diet. All nutritional information is based on estimated third-party calculations. Each recipe and nutritional value will vary depending on the brands you use, measuring methods, and portion sizes per household.

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Jessica Gavin

I'm a culinary school graduate, cookbook author, and a mom who loves croissants! My passion is creating recipes and sharing the science behind cooking to help you gain confidence in the kitchen.

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24 Comments Leave a comment or review

  1. Larry Otter says

    Jessica, I love your recipes and appreciate all the time and effort you put into explaining the science behind what you do. I have texted you a couple of times, to let you know how much I’ve enjoyed your recipes, but wanted you to hear it again! Thank you so much!!

  2. Katie Kruse says

    I haven’t made a cake in 30 years….and there is a reason for that! I made this and it turned out great! Why, because you explained it perfectly! I appreciated the discussion on the temperature of the butter and the reasoning behind the cake flour. Thank you so much! My 92 year old mother, Joan, also says thank you. She lives in an elderly community with no visitation allowed. So she said the cake made her day when it was delivered!

  3. Michelle Bellemare says

    I tried your Chicken Yakatori skewers as my first recipe and was hooked. This has always been my favorite cake and is made for my birthday each year in December.
    I am going to pass the recipe around, lol. One question…will this recipe be in your cookbook? I just bought the book and am hoping to find lots of your current recipes in it. Thanks for these no-fail recipes!

    • Jessica Gavin says

      Hi Michelle- Thank you for making the recipes! The pineapple upside-down cake is what I make for my husband’s birthday too! Yes, the cake recipe is in the cookbook too. Yay!

  4. Michael Kane says

    I’ve made this recipe a couple of times. Both times it came out perfect, delicious and quite attractive. The first time was my first attempt at an upside down cake. I used a 9” round metal nonstick cake pan and was so happy when the cake slid right out!

  5. Dawn C. says

    I have made this type of cake for decades. And I Love of Jessica’s recipes. I did something really wrong but can not figure out what. It was too sweet and WAY too much butter for me to eat it. I followed it to a T, so I do not know why it turned out disappointingly. Sorry, Jessica. I am stumped. ( I took a picture of it)

    • Jessica Gavin says

      Hi Dawn- Will you email me the pic? This cake is definitely for those with a sweet tooth. Do you think the topping was too sweet and buttery, or the cake itself?

  6. AldiAllYear says

    The caramel topping on this is soooo good! My cake batter looked more like a quick bread, so I added more liquid. It turned out kind of dense, but still tasted amazing. Next time, I’m going to do better about following the advice on the temperature of the ingredients, using cake flour instead of all purpose, etc.

  7. Brenda says

    If this was a true classic Pineapple Upside Down Cake you would know that actually it is just butter and brown sugar melted in a cast iron skillet, and then the rest of your ingredients.

  8. Jerel says

    Hi Jessica! We don’t have a stand mixer. Any suggestions or changes for a hand mixer for the cake part?

    • Jessica Gavin says

      I would follow the same directions, just use the thicker paddle blades vs. the whisk the texture should be thick like the photo.

  9. Judy Caywood says

    Jessica, Hi. My husband would be so happy to have me make this for him for Father’s Day. Since I am on Keto and would not be eating any I’m wondering if this cake would freeze well. I’m sure he could not eat it all himself. Or I could make him a smaller version of it and perhaps cut the recipe in half. Thanks always for your great spirit and wonderful recipes. Judy

    • Jessica Gavin says

      Hi Judy! I think this cake would freeze ok, but in my opinion, it tastes best fresh. A smaller cake would work 🙂

  10. Marilynne Wilson says

    Jessica, you read my mind! I was going to make this recipe this weekend! One question: can I use a cast iron skillet? That is what I usually use.

    • Jessica Gavin says

      Yes, you can use a cast iron skillet, what size do you have? I would bake the skillet placed on top of a sheet pan just in case any batter flows over.

      • Marilynne Wilson says

        Jessica, I made it in a Pyrex dish and it came out beautiful and delicious!!!! This is a keeper! Thank you so much for your wonderful recipes. I had another thought….could I use the recipe and bake in a muffin pan for individual cakes?