” Pineapple upside-down cake: A melt-in-your-mouth buttery vanilla cake with a  caramelized pineapple topping”

Recipe Tutorial: Watch me make this pineapple upside-down cake from start to finish!

The Recipe Story

Have you ever had a classic, from-scratch pineapple upside-down cake that just melts in your mouth with the most buttery-tasting crumb and the best sweet & sticky caramelized pineapple topping? If not, here ya go! You’re so welcome!

I never thought those words would come out of my mouth.

Ya, see me and pineapple upside-down cake has had a rocky relationship over the past years. I use to hate it! Like… really hate it! It just reminded me of an old lady cake and all the homemade versions I had were dry, crumbly,  bland, and just lacking…well..personality! It wasn’t a big deal though, it’s not like I had to ever try it again.

And then along comes my husband.

Classic Pineapple upside-down cake

Out of all the cakes I make and love do you want to know what his favorite is? The one he requests for every. single. freakin. birthday?  Yep, dadgum old lady pineapple upside-down cake! I’d normally just get a boxed Duncan Hines yellow cake mix,  throw some extra stuff in there to transform it into a pineapple upside-down cake, and call it a day. Or make this delicious pineapple dessert that we both love.

Well, my guy’s birthday is coming up and I think it’s fair to say he definitely deserves a really good from-scratch pineapple upside cake after all these years. I’m sure I’ve bragged enough about my husband on this blog but he really is one of the most amazing human beings I’ve ever met. He’s just so kind and helpful to EVERYBODY. Whew, how he puts up with my crazy behind is beyond me!

Let the marathon cake testing begin!

I pulled a recipe offline to test it out before his birthday. FAIL. So then I tried another popular one. FAILED. Ok so maybe it was me, maybe I just did something wrong. FAILS again. In all fairness, the cakes were actually ok but they needed more… sin! More butter, more sugar, more…something!!

Normally I don’t do back-to-back recipe developing/testing/tweaking unless I plan on putting it on my blog but this was one challenge I couldn’t turn down. My baby was getting his from-scratch pineapple upside-down cake and it had to be incredible.  After making my own versions which were FAILS too LOL I was about ready to go back to my boxed gig but I just couldn’t.  I DO NOT LET ANY RECIPE WIN, EVER lol. I literally can’t stop with a recipe until I get it right.  After six cakes my kids were like “not again please!” lol Thankfully this is a very basic recipe with simple ingredients

Pineapple upside down cake

So as I was making my final version, I decided to check in with my never-wrong intuition (Yep, I use my gut instincts for the smallest of things lol )That’s when the idea to use heavy whipping cream AND milk instead of the other liquid combos I had tried (heavy cream & pineapple juice, milk and pineapple juice, just milk, etc. ) Along with some other tips like adding that extra 2 tablespoons of sugar and shortening, whodathunkit!  The results? OMG PERFECTION!! It was EXACTLY the texture and flavor I was going for. Soft but dense enough to withstand that heavy, delicious topping! And a rich buttery flavor that wasn’t just an afterthought.

I am converted and now LOVE pineapple upside-down cake or at least THIS recipe!

Ladies & gentlemen, I present to you the BEST pineapple upside-down cake I’ve ever had. My husband got an early birthday cake and it rocked his world! He said, “yeah this is definitely blog-worthy”.  So here we are!

Oh but promise me one thing, you MUST eat it warm!  Pineapple upside-down cake is just not the same when it’s room temperature or cold. Boooo! 

 What is pineapple upside-down cake?

Pineapple upside-down cake is a basic butter-vanilla cake with a caramelized topping consisting of pineapples and maraschino cherries. The cake is prepared “upside-down” starting with the topping and pouring the cake batter on top. After it is baked, it is flipped over the topping is on top.

Southern Pineapple upside-down cake

Pineapple Upside Down Cake Ingredients: Cast Of Characters

  • Pineapple rings: Fresh or canned
  • Maraschino cherries: These guys just make this cake look so pretty, cheery, and bright! I’m not a cherry fan but I can handle this tiny amount! They go great with the pineapple.
  • Butter- Butter is the flavor of the cake part and it’s incredible
  • Butter-flavored shortening– You can use all butter but it won’t have the taste and crumb texture that shortening gives. Just use butter-flavored shortening ok? You can even go for the coconut oil one (Spectrum brand)
  • Brown sugar: Yessss ma’am! That’s how we get that caramelize action going
  • Granulated sugar: Because you gotta add some sweetness. Enough for the cake to stand on its own, yet not be too sweet with the caramelized pineapples. It’s possible.
  • Vanilla extract: To add some slight vanilla flavor
  • All-purpose flour: this is a small, one-layer cake so we don’t need too much
  • Baking powder and baking soda: To give the cake some lift so it isn’t too dense.
  • Large Eggs: To help bind it all together and give more lift and moisture
  • Heavy whipping cream: The BEST liquid ingredient for the BEST pineapple upside-down cake texture
  • Milk: To keep from using too much heavy whipping cream but still add moisture and flavor.

The Topping AKA The King Daddy

When it comes to pineapple upside-down cake, the topping is the star! It’s all about that sweet and sticky brown sugar caramelized pineapples and glazes! The topping consists of melted butter, light brown sugar, pineapple slices, and maraschino cherries. As the cake cooks that buttery glaze creeps up along the edges and bakes right ins, resulting in a caramelized crisp, butter crust, which to me is the best part!!

The Butter Vanilla Cake AKA The Queen Mama

This cake is FANTASTIC!!!!  It just melts in your mouth and takes pineapple upside-down cake to the next level. It’s now good enough to eat plain. The cake was the part that kept failing on me before but with the addition of butter-flavored shortening, heavy cream, a tad bit more sugar, and reducing the baking time, the results are perfection!  The crumb is soft, yet firm enough to withstand that heavy, rich topping. And the flavor has so much more personality now! So buttery with a light hint of vanilla.

Best Pineapple upside down cake

Fresh or Canned Pineapple Rings?

Normally I’d so go with fresh! There is nothing like the smell and taste of ripe, sweet pineapple. But canned works just as good if you’re in a pinch, although can often purchase fresh pineapple rings from most grocery stores. I like to use canned pineapple rings that are in their own juices (not syrup) like Del Monte Deluxe Gold (black can). They are quick, easy, and perfectly sweet! You can also use pineapple chunks if you’d like.

Overview: How to Make this Pineapple Upside-down cake recipe

TOPPING: Start by pouring melted butter into your glass pie plate. Next, sprinkle on an even layer of brown sugar. Arrange the pineapple slices and maraschino cherries on top.

CAKE BATTER: In a large bowl whisk together flour, baking powder, and salt. Set aside. In another large bowl cream together butter, shortening, granulated sugar, and brown sugar using a hand mixer. Mix in eggs and vanilla extract. Gradually mix the dry ingredients into the wet ingredients while alternating with the milk and heavy whipping cream just until combined and the mixture is fluffy.  Spoon the batter evenly over the topping and spread it into an even layer.

BAKE: Bake the cake in preheated 325 F. oven for 40 minutes. Cover loosely with tented foil and bake for another 30-35 minutes or until a toothpick inserted into the center comes out clean.

COOL: Let the cake cool on a wire rack for 15 minutes (no longer than that) and invert it onto a cake stand or serving platter.

SERVE: Let cool for about 5 more minutes. Slice and serve warm. Vanilla ice cream or homemade whipped cream is fab with this!


  • Don’t over mix. Be careful to combine the ingredients just until combined. Overmixing will result in a crumb that is way too fluffy and possibly dry. We are aiming for a crumb that is tight, slightly dense yet soft enough to melt in your mouth.
  • Don’t leave the cake in the pan too long. It’s important that the cake is still hot when you go to invert it. Only let it cool in the pan for about 15 minutes.

Best Pineapple upside-down cake


Which cake pan should I use? I ALWAYS use a glass 9.5  deep pie plate. I just love the way the glass cooks this cake without anything sticking.  And bonus I can see the bottom when I flip it over to ensure nothing is sticking.  I’ve never cooked this cake in a cast-iron skillet or dark pan so I can’t make any recommendations for those.

How do you store pineapple upside-down cake? Store the cake covered in plastic or in a cake container in the fridge for 2-3 days. This cake is BEST eaten the same day and served hot.

How many calories does this cake have? Zero. Are there any other questions?

How do you invert (flip over) a pineapple upside-down cake? Using a glass pie plate with handles helps so much. I use this one. To invert, place your cake stand or serving board over the pie plate. Grab the handles on the pie plate and the cake stand so that you have them both pinched together. (see video for demonstration). Quickly flip it over so that pie place is now on the cake stand. Very carefully remove the pie plate. This is why I ONLY bake pineapple upside-down cakes in glass dishes! I can see if anything is sticking and gently wiggly it until it releases.


Classic Pineapple upside-down cake

Get the Recipe: Pineapple Upside-Down Cake

4.96 from 25 ratings
Pineapple upside-down cake: A melt-in-your-mouth buttery vanilla cake with a  caramelized pineapple topping.
Prep Time: 20 minutes
Cook Time: 1 hour 15 minutes
Servings: 8 people



  • 6 tablespoons unsalted butter, melted
  • cup light brown sugar, packed
  • 1 20 oz. can pineapples rings (in their own juices, not syrup), (about 11 slices, dried with paper towels)
  • 11 maraschino cherries


  • 4 tablespoons unsalted butter, room temperature
  • 4 tablespoons butter-flavored shortening, (a must, don't use plain)
  • ½ cup + 2 tablespoons granulated sugar
  • ¼ cup light brown sugar, packed
  • 2 eggs, room temperature
  • ½ teaspoon vanilla extract
  • cups all-purpose flour
  • teaspoons baking powder
  • ¼ teaspoons salt
  • ½ cup heavy whipping cream
  • ¼ cup whole milk


Make the Topping

  • Preheat the oven to 325 F. Move the oven rack to the middle of the oven. (Place a baking sheet on the bottom rack just in case juices from the cake bubble over a bit.)
  • In a deep 9.5-inch glass pie plate, add melted butter and spread out to cover the bottom.
  • Sprinkle brown sugar evenly over the butter.
  • Place a whole pineapple ring in the middle of the pan.
  • Slice the other pineapples in half and place the halves around the middle pineapple.
  • Place a cherry in the center of each space. (Refrigerate until ready to use)
    Step-by-step Pineapple upside-down cake

Make the Batter

  • In a large bowl, cream together butter, shortening, white sugar, and brown sugar.
  • Mix in eggs and vanilla extract. Set aside.
  • In a separate bowl, whisk together flour, baking powder, and salt.
  • Gradually add the dry ingredients to the wet ingredients while alternating between the heavy whipping cream and milk.
  • Mix just until batter is combined and fluffy, do not over mix.
  • Pour batter over pineapples and carefully spread out into an even layer.

Time to Bake!

  • Bake for 40 minutes. Then cover loosely with tented foil (to prevent further browning) and bake for another 30-35 minutes (may need shorter or longer) or until a cake tester inserted into the middle of the cake comes out clean.
  • Remove from the oven and let the cake cool for about 15 minutes.

Time to Invert The Cake!

  • While the cake is still warm, place a cake stand on top of the pie plate and carefully flip both over. (Use oven mitts since the bottom of the pie plate will be hot! See video for demonstration)
  • Carefully remove the pie plate. Serve the cake warm.


Cuisine: American, southern
Course: cake, Dessert
Tried this recipe?Mention @divascancook on Instagram or tag #divascancook.