Saturday, July 13, 2024
It's Sweet to Share!

Is the Secret to Making the Best Old Fashioned Pineapple Upside Down Cake Double Caramel?

It's Sweet to Share!

There are some desserts, though wildly popular, I’ve just never been drawn to. Desserts like Boston Creme Pie, Cherry Pie, Tiramisu (probably because mine turned out awful), and Old Fashioned Pineapple Upside Down Cake. 

What a mistake.

Old Fashioned Pineapple Upside Down Cake

Up until very recently, Pineapple Upside Down Cake could be found in the above list. Gabriel, quite aptly said he thought it always sounded like a “cheap dessert”. Having never found a reason, or excuse to make this cake, there it wasted away in the ‘cheap’ category. 

Old Fashioned Pineapple Upside Down Cake

But then about a week ago we invited some friends over for dinner, and what do you know? They requested this very cake for dessert. As a polite host, who had demanded a request for dessert, I quietly obliged.

I really should do more things I don’t feel like doing. This cake is A. to the M.A.Z.I.N.G. In fact, it may very well now be my ultimate favorite cake.

Old Fashioned Pineapple Upside Down Cake

To Cherry or Not to Cherry?

The answer is always no. 

We are using fresh pineapple, so bottled maraschino cherries have no place on this fresh Caribbean cake. 

How to Make Old Fashioned Pineapple Upside Down Cake

When I first made this old fashioned pineapple upside down cake, I made a very wonderful mistake by adding ¾ cup of butter to the caramel topping instead of ¾ stick of butter! A difference of 6 extra tablespoons! As such, I ended up getting to double the caramel topping. 

It’s the best thing to ever happen to Pineapple Upside Down cake, and the secret to making this already incredible dessert that much better!  

The resulting candied pineapple cooked in a cast iron pan is perfection. The moist butter rum cake seeps into the pineapple and increases the flavor of every single bite! 

This old fashioned pineapple upside down cake is the consummate in fresh, warm, comfortingly sweet confections. It has a rich flavor that is deep and resonates with each bite.

Is the Secret to Making the Best Pineapple Upside Down Cake Double Brown Sugar Caramel?

Old Fashioned Pineapple Upside Down Cake

Catherine Olson
Baked in a cast iron skillet with double the brown sugar caramel topping this old fashioned pineapple upside down cake is everyone's favorite cake!
Prep Time 45 minutes
Cook Time 45 minutes
Course Dessert
Cuisine American
Servings 8 pieces


  • 10" Cast Iron Skillet


Double Brown Sugar Caramel Topping

  • 1 fresh pineapple
  • 12 tablespoons unsalted butter
  • 1 ½ cups packed light brown sugar

Cake Batter

  • 1 ½ cups all-purpose flour
  • 2 teaspoons baking powder
  • ¼ teaspoon salt
  • 6 tablespoons unsalted butter softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla
  • 1 tablespoon dark rum imitation works great
  • ½ cup unsweetened pineapple juice can use half the pineapple for juicing


Double Brown Sugar Caramel Topping

  • Cut pineapple into ½ inch thick pieces and cut out the center of each piece
  • Set aside pineapple
  • In 10” cast iron pan melt butter and add brown sugar
  • Simmer over medium-high heat until mixture comes to a boil stirring constantly
  • Cook for 5-6 minutes
  • Remove from heat and allow to cool for 10 minutes
  • Arrange pineapple on top of sugar mixture in skilet, overlapping pieces slightly until the base of the pan is covered

Cake Batter

  • Beat butter and sugar in a large bowl with an electric mixer until light and fluffy
  • Add eggs one at a time, beating well after each addition
  • Add vanilla and rum
  • Incorporate half of the flour, baking powder, and salt and mix on low just until blended
  • Add pineapple juice and beat again until blended
  • Add remaining flour, again just until blended
  • Batter may appear slightly curdled
  • Spoon batter over pineapple in the cast iron pan and spread evenly until pineapple slices are covered
  • Bake at Fahrenheit 350° for 35 to 45 minutes
  • Remove from oven and let sit for 5 minutes
  • Carefully invert cake onto a plate
  • Serve cake warm or at room temperature

Can I Use Canned Pineapple for this Cake?

Of course! Do whatever makes it easier for you!

But I have to tell you, fresh pineapple really makes this cake extra special!

Do I Have to Use a Cast Iron Pan?

No. You can use a regular cake pan.

Be sure not to use a springform pan, or you’ll risk losing some of the caramel topping! And of course, that would be shame since we doubled it to make this cake extra special!

Slice of cake

Just look at how sticky and gooey and delicious that shiny caramel looks soaked into the pineapple!

Make This Amazing Old Fashioned Pineapple Upside Down Cake

If you make this Old Fashioned Pineapple Upside Down Cake tag @Fahrenheit350sweets on Instagram so I can see it! And I’d love it if you left a review and a comment below! 

More Yummy Fruit Based Cake Recipes to Bake at Fahrenheit 350°!


It's Sweet to Share!


  1. Leslie, I know! I've had some weird aversion towards cherries my whole life until I finally ate one a couple years ago! I love them! I'm sure I'll be tackling cherry pie soon!

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