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Pineapple Upside-Down Cake

Pineapple Upside-Down Cake



  • Nonstick vegetable oil spray
  • 1 1/4 cups (packed) dark brown sugar
  • 1/2 cup (1 stick) unsalted butter, cut into 1-inch pieces


  • 2 teaspoons baking powder
  • 1/8 teaspoon ground cardamom
  • 1/2 cup (1 stick) unsalted butter, room temperature, cut into 1-inch pieces
  • 2 teaspoons vanilla extract

Special Equipment

  • A 10-inch-diameter cake pan with 2-inch-high sides; a small round cookie cutter (about 1 inch diameter)

Recipe Preparation


  • Preheat oven to 350°. Coat cake pan with nonstick spray; set aside. Cook brown sugar and butter in a small deep heavy saucepan over medium heat, whisking occasionally, until mixture is bubbling and sugar is completely dissolved. Boil, whisking occasionally, until caramel darkens, thickens, emulsifies, and pulls away from sides of pan, about 3 minutes.

  • Remove from heat and whisk in bourbon (mixture will bubble vigorously). Return caramel to a boil; cook for 1 minute. Pour caramel into prepared cake pan and swirl pan until bottom is completely covered. Let cool completely before proceeding (caramel will harden).


  • Cut skin from pineapple, making sure to remove all brown eyes. Cut 1/4-inch–1/3-inch-thick rounds from pineapple. Using cookie cutter, remove core to form rings. (If pineapple is very juicy, drain rings briefly on paper towels.) Arrange pineapple rings decoratively on top of caramel in cake pan without overlapping. (Cut rings into smaller pieces to fill any large gaps, if desired.)

  • Whisk flour, baking powder, salt, and cardamom in a medium bowl. Using an electric mixer, beat sugar and butter in another medium bowl until light and fluffy, 5–6 minutes. Beat in vanilla. Add eggs one at a time, beating to blend between additions. Scrape down sides of bowl. Beat egg mixture until doubled in volume and very light and fluffy, about 2 minutes. Scrape bottom of bowl well, making sure to incorporate all butter into eggs. Beat for 1 minute longer.

  • Beat in flour mixture in 3 additions, alternating with sour cream in 2 additions, beginning and ending with dry ingredients. Scrape batter into pan; smooth top.

  • Bake cake until a tester inserted into the center comes out clean, 50–60 minutes. Transfer to a wire rack. Let cake cool in pan for 30 minutes. Run a sharp knife around sides of pan to loosen cake; tap bottom of pan and invert cake onto a large plate. DO AHEAD: Cake can be made 8 hours ahead. Cover with a cake dome and let stand at room temperature.

Recipe by Cakes Ale in Decatur GA,Photos by Jonathan Lovekin

Nutritional Content

10 servings, 1 serving contains: Calories (kcal) 490 Fat (g) 23 Saturated Fat (g) 14 Cholesterol (mg) 105 Carbohydrates (g) 64 Dietary Fiber (g) 1 Total Sugars (g) 44 Protein (g) 4 Sodium (mg) 320

Related Video

Old-School Pineapple Upside-Down Cake

Reviews SectionThis is a very solid (and sweet!) pineapple upside-down cake. I used to make the classic 50s version with canned pineapple and maraschino cherries, which was always one of my childhood favorites. I was intrigued to try with fresh pineapple. While I really like the cake, especially the touch of bourbon to the caramel, I didn't think this cake was that different from the old-school version. Perhaps I didn't quite cook the caramel long enough (I also make the cake in a cast-iron skillet) because it just sunk into the cake and the pineapple was cooked, but not brown. Then again, this may be my Proustian moment and no pineapple upside-down cake will live up the one of memories...Santa Barbara, CA04/14/20Let me start by responding to Sarabachis' comment about when to add the sour cream. It's in the instructions- it goes in turns with the flour mix.I find it best to read the recipe three times before I start because I know that BA recipes are the most reliable out there- but I on the other hand not so much.I love this recipe- it is like pineapple upside down meets custard cake. The cake is so rich and creamy and yet the pineapple is browned and marries the carmel so well. This is even after converting to gluten and dairy free! If you need to do so, I recommend Cup4Cup all purpose flour plus cornstarch to replace the cake flour and Earth Balance non-dairy butter sticks and Good Karma sour cream for the dairy replacements. Cheers!This is my go-to pineapple upside-down cake. It’s a little more time-consuming than the average cake recipe, but it’s worth the extra steps and care. The cake is light and fluffy but moist. The caramel and pineapple are decadent and delicious. This is a show-stopper, crowd-pleaser.Great recipe, but like so many, you have completely forgotten to specify when to add an ingredient....sour cream.SarabachisSan Francisco, California05/26/18How do I read the reviews?

Pineapple Upside Down Cake

This pineapple upside down cake is soft and buttery with a caramelized brown sugar pineapple & cherry topping. Its juices seep down into the cake, adding even more luscious flavor and texture. A classic favorite using canned pineapple and maraschino cherries, this retro cake is served upside down and perfect any time of year.

I love learning in the kitchen and I’m always working hard to improve my skill. With constant practice comes the opportunity to bring you the best recipes I can. This is an exciting post!

Pineapple Upside Down Cake

This is the classic upside down cake which was a winner in the first Dole recipe contest in 1926.

Prep time 15 min

Total time 55 min

Servings 10

Calories per serving 380

can (20 oz.) DOLE® Pineapple Slices

cup butter or margarine, melted

pkg. (2-layer size) PILLSBURY Pineapple Flavored or Yellow Cake Mix

Drain pineapple slices reserve 3/4 cup juice.

Stir together melted butter and brown sugar in 12-inch skillet with heat-proof handle. Arrange pineapple slices in sugar mixture. Place cherry in center of each pineapple slice.

Prepare cake mix according to package directions, replacing some of the water with reserved 3/4 cup juice that is needed to prepare the batter. Pour batter evenly over pineapple.

Bake at 350 Fº, 35 to 40 minutes or until toothpick inserted in center comes out clean. Cool 5 minutes. Loosen edges and invert onto serving platter.

Note : Cake can be baked in 13 x 9-inch baking pan instead of skillet. Prepare and assemble cake as above except cut two pineapple slices in half and place whole slices along edges of pan and halved slices in center. Place cherries in center of slices. Bake and cool as above.

Pineapple Upside-Down Cake

This classic cake, with its moist, flavorful topping of pineapple rings and cherries (nuts optional), has been an American favorite for at least 90 years. It became popular after an early 20th-century Dole engineer invented a machine that would slice that company's signature product — pineapple — into perfect rings the first recipe appeared in print in 1923.

This particular recipe, baked in a 9" round cake pan, makes a thin layer of cake topped with perfectly spaced pineapple rings. Baking in an 8" pan would yield a taller cake, but the rings would be crowded together. Either way, the cake is buttery, brown sugary, and VERY tasty.


  • 4 tablespoons (57g) butter
  • 1/2 cup (106g) light brown sugar, firmly packed
  • 1/4 teaspoon cinnamon
  • 1/4 teaspoon ginger
  • 20-ounce can pineapple rings in juice, drained
  • candied red cherries or maraschino cherries
  • pecans or walnuts, halves or diced optional
  • 3 tablespoons (43g) butter, at room temperature, at least 65°
  • 3/4 cup (149g) granulated sugar
  • 1 large egg, at room temperature
  • 1/2 teaspoon salt
  • 1 3/4 teaspoons baking powder
  • 1 teaspoon vanilla extract
  • 1/8 teaspoon coconut flavor, optional
  • 1 1/3 cups (159g) King Arthur Unbleached All-Purpose Flour
  • 1/2 cup (113g) milk, at room temperature


Preheat the oven to 375°F. Lightly grease a 9" round cake pan.

To make the topping: Melt the butter, and mix with the brown sugar, cinnamon, and ginger. Spoon the mixture into the prepared pan.

Space the pineapple rings atop the brown sugar mixture. Place a cherry in the center of each ring. If you're using nuts, scatter them in any empty spaces.

To make the cake: Beat the butter and sugar until fairly smooth.

Beat in the egg, then the salt, baking powder, vanilla, and coconut flavor.

Add the flour alternately with the milk, mixing at medium speed and beginning and ending with the flour. Once the last of the flour is added, mix briefly, just until smooth.

Spoon the thick batter into the prepared pan, spreading it to the edges of the pan. It may not cover the pineapple entirely that's OK.

Bake the cake for 30 to 35 minutes, until a toothpick or cake tester inserted into the center comes out clean.

Remove the cake from the oven, wait 3 minutes, then turn the pan over onto a serving plate. Wait 30 seconds, then lift the pan off. If anything sticks in the pan, just lift it out and place it back on the cake.


I use Dunkin Hines pineapple supreme cake mix.

I always use 1 cup of pineapple juice instead of water. Delicious!

I use a cast iron skillet and have made this wonderful birthday cake for the last 59 years. My husband's favorite. thank you Duncan Hines.

Why does the recipe call for an 8 X 13 inch pan but cake in photo is circular ?

@lurleen. You can use the pineapple juice. I use it every time.

why can't you use pineapple juice in batter -LMB

I make this with fresh bananas. Same method but instead of pineapple cut bananas lengthways in butter sugar base. Top with cake mix. Wonderful warm with ice cream

I made this one last week and my hubby love it!

I made this one day. Was kind of dissapointed that it didn't rise up more. Not sure if it was something that I did wrong or not. Still it was good. :> A much faster way to make then one from scratch.

It's been 10 years, maybe you know the difference between then and than now. but then.

Know your meme: THEN is used for time: First I stole a panda bear, then we drank malt liquor together. THAN is used for comparison: I'm much better at holding my liquor than a panda bear. These are different words.

Gluten-Free Pineapple Upside-Down Cake

Finally, those of us on gluten-free diets can dig into this classic cake, based on our Gluten-Free Yellow Cake Mix. Its moist, flavorful topping of pineapple rings and cherries (nuts optional) has made it an American favorite since 1911, when a Dole engineer invented a machine that would slice pineapple into perfect rings. This cake is wonderfully buttery/brown sugary, and VERY tasty.


  • 4 tablespoons (57g) butter, cold
  • 1/2 cup (106g) light brown sugar, packed
  • 1/4 teaspoon cinnamon
  • 1/4 teaspoon ginger
  • 20-ounce can pineapple rings in juice, drained, juice saved
  • candied red cherries or maraschino cherries
  • diced pecans or walnuts, optional
  • 2 tablespoons (25g) vegetable oil
  • 8 tablespoons (113g) butter, softened
  • 1 box King Arthur Gluten-Free Yellow Cake Mix
  • 4 large eggs, at room temperature
  • 2/3 cup (152g) pineapple juice (from the can of pineapple rings)


Preheat the oven to 350°F. Bake this cake in either a 9" round or an 8" square cake pan there's no need to grease the pan.

To make the topping, melt the butter, and mix with the brown sugar, cinnamon, and ginger. Spoon the mixture into the cake pan.

Drain and save the juice from the pineapple rings. Space the rings atop the brown sugar mixture: eight pineapple rings will fit in a 9" round pan, and nine pineapple rings in an 8" square pan.

Place a cherry in the center of each pineapple ring. If you're using nuts, scatter them in any empty spaces.

Follow the box's directions for making the cake batter, but use 2/3 cup of the juice from the pineapple rings instead of the milk called for. If you don't have quite 2/3 cup of juice, use water to make up the difference.

Spoon half the batter (about 2 1/2 cups) into the pan, spreading it over the fruit to the edges. See tips, at left, for tasty suggestions on how to use the rest of the batter.

Bake the cake for 40 to 45 minutes, until it's firm on top, the edges of the crust are brown, and the internal temperature is between 210°F and 212°F.

Remove the cake from the oven, run a spatula around the edge, wait 3 minutes, then turn the pan over onto a serving plate. Wait another 30 seconds, then lift the pan off. If anything sticks to the pan, just scrape it out and spoon it back on the cake. Best served warm.

Tips from our Bakers

This particular recipe uses only half the batter made from our Gluten-Free Yellow Cake Mix. Use the rest to make a second layer of cake, 10 cupcakes, or even a second upside-down cake to freeze. A plain 9" round cake takes 25 to 30 minutes to bake cupcakes, 20 to 25 minutes. If you make the second upside-down cake, you'll need to make a second batch of topping topping amounts are for one cake.

If you make a plain layer cake or cupcakes out of the remaining batter, the pineapple flavor is very mild and would probably harmonize just fine with any frosting. Our favorites include vanilla, coconut, and citrus. You could also use more pineapple (or other tropical fruits) and coconut custard to make a trifle.

Be aware: some of your baking ingredients can be a hidden source of gluten. Learn more at our blog post: For gluten-free baking, think beyond just flour. For additional information on King Arthur-produced products, read the complete details of our allergen program, including our contact-prevention practices.

Pineapple Upside Down Bundt Cake

1/2 cup butter (1 stick), melted
1/2 cup packed brown sugar
1 Can pineapple rings in 100% juice (reserve the juice)
1 Jar maraschino cherries
1 Box yellow or pineapple cake mix
1 4-serving box instant vanilla pudding
3 eggs
Vegetable oil


Preheat the oven to 350 degrees F.
Prepare the bundt pan by generously applying pan release (recipe below) or non-stick spray.
Melt the butter and evenly pour it into the bottom of the pan. Sprinkle with the brown sugar.
Cut the pineapple rings in half and alternate with the maraschino cherries around the bundt pan as shown in the picture. Set aside.
In a stand mixer or large bowl, stir the cake mix and pudding mix together. Drain the pineapple juice into a measuring cup and add enough milk to make 1 Cup of liquid.
Add this with the eggs and the amount of oil called for in the recipe to the cake mixture following the instructions on the box.
Carefully pour the batter over the fruit and bake as instructed for a bundt cake. The cake is done when an inserted knife comes out clean.
Cool for 10 minutes in the pan. Slide a knife around the edges including the inner ring.
Invert the cake onto a serving plate. Slice between the pineapple rings and serve warm or room temperature.
And Enjoy…!

In addition to this being an easy cake to make, another great things is that you only need a few ingredients. And best of all, the ingredients you need are probably in your home right now! With a box of cake mix, 1.5 sticks of butter, and 2 cans of pineapples you are ready to get started.

I mentioned that this is an easy cake to make, but what exactly does that mean? You are probably wondering if you need some baking knowledge or if anyone can really make this with ease. You truly don’t need to be a professional baker. Anyone can make this cake and look like a baking superstar!

My kids always like to “help” me make things. And, reluctantly, I will allow them to help from time to time. Honestly, making a pineapple dump cake is a cake that kids can help with and it won’t be a complete nightmare for you. Seriously!

Making The Dump Cake

Once you have your ingredients in front of you, you will can pull this cake together in 6 or 7 minutes. Next, you will need to melt the butter and distribute it evenly on the bottom of a 9 x 13 pan. Then, you just have to layer the ingredients starting with the pineapple juice, then the pineapples, next the cake mix, and then the cubed butter at the very top. Finally, just pop the pan in the oven and wait approximately 50 minutes before it will be done. While the cake is baking, you will LOVE that sweet smell coming from your oven.

Go all out and top the cake with either ice cream, homemade whipped cream, or both!

  • Topping:
  • 1/2 stick (1/4 cup) unsalted butter (melted)
  • 2/3 cup light brown sugar ( firmly packed)
  • 3 cups fresh pineapple, cut into 1-inch chunks (about 1 pineapple)
  • Cake:
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder (double-acting)
  • 1/2 teaspoon salt
  • 1/2 teaspoon cinnamon
  • 1 stick (1/2 cup) unsalted butter (softened)
  • 2/3 cup sugar (granulated)
  • 2 large eggs
  • 1 teaspoon pure vanilla extract
  • 3/4 cup milk
  • Garnish: whipped cream or vanilla ice cream

Make the Topping

In a small bowl, stir together the butter and the brown sugar until it's well-mixed and spread the mixture evenly in a well-buttered 9- by 2-inch round cake pan.

Pat the pineapple dry between several thicknesses of paper towels and arrange it evenly on the sugar mixture.

Make the Cake

Preheat the oven to 350 F.

Sift together into a bowl the flour, baking powder, salt and cinnamon.

Place the butter and sugar in another bowl and cream with an electric mixer until the mixture is light and fluffy.

Add the eggs, one at a time, beating well after each addition, and beat in the vanilla.

Add the flour mixture alternately in batches with the milk, beginning and ending with the flour mixture and beating well after each addition.

Pour the batter into the pan, spreading it evenly, and bake the cake in the middle of the oven for 45 to 55 minutes, or until a tester comes out clean.

Let the cake cool in the pan on a rack for 15 minutes, then run a thin knife around the edge and invert the cake onto a plate.

Serve the cake warm or at room temperature with the whipped cream or vanilla ice cream.

Emphasize the tropical flavor of pineapple upside-down cake by adding maraschino cherries to the topping. Arrange them along with the pineapple on top of the topping sugar mixture, alternating each one.

Substitute rings for chunks for a pretty presentation. Cut fresh pineapple into rings or use canned pineapple rings.

Use a Bundt cake pan for a more spectacular presentation. Use fresh or canned pineapple rings with this pan. Cut the rings in half and stand them vertically against the sides of the pan for an interesting look.


  • ¾ cup packed dark brown sugar
  • 3 tablespoons unsalted butter, melted
  • ½ teaspoon kosher salt, divided
  • 2 (8-oz.) cans pineapple slices in juice, drained
  • ¾ cup granulated sugar
  • ½ cup canola oil
  • 1 large egg
  • 1 large egg yolk
  • 1 teaspoon vanilla extract
  • 2 cups (about 8½ oz.) all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ¼ cup whole milk

Stir together brown sugar, melted butter, and ¼ teaspoon of the salt in a small bowl. Generously coat a 6- to 7-quart round or oval slow cooker with cooking spray. Spread brown sugar mixture evenly in bottom of slow cooker. Arrange pineapple slices over brown sugar mixture, trimming as necessary to make an even layer.

Beat granulated sugar, oil, egg, and egg yolk in a medium bowl with an electric mixer on medium speed until slightly thickened and smooth, about 2 minutes. Stir in vanilla. Whisk together flour, baking powder, baking soda, and remaining ¼ teaspoon salt in a medium bowl. Stir half of the flour mixture into batter until almost incorporated. Add milk, and stir to combine. Add remaining flour mixture, and stir just until incorporated. Spoon batter over pineapples, and spread to edges of slow cooker with an offset spatula.

Drape a clean kitchen towel over slow cooker, and place lid over towel. Pull towel taut under lid. Cook on LOW until a wooden pick inserted in center comes out clean, about 2 hours and 30 minutes. Remove slow-cooker insert to a wire rack, and let stand until cool enough to handle, about 20 minutes. Place a cutting board or serving plate over slow-cooker insert, and carefully invert to release cake. Serve warm or at room temperature.