It's Sweet to Share!

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

It's Sweet to Share!

*updated 2020

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. 

However, because I’m obsessed with having a well rounded repertoire and knowledge of all aspects of dessert making, I have decided they all must be conquered (sooner or later)! 

There is something to be said for doing something that you don’t necessarily want to do. It builds character; it broadens horizons; it opens doors, and in some cases, it makes you fall in love.

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.

In fact, since updating this blog post 8 years later, this cake still remains one of my absolute favorite cakes! 

Old Fashioned Pineapple Upside Down 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. 

A Big Mistake

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 mins
Cook Time 45 mins
Course Dessert
Cuisine American
Servings 8 pieces

Equipment

  • 10" Cast Iron Skillet

Ingredients
  

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

Instructions
 

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!

Like this recipe? Check out more caramel cake recipes!


It's Sweet to Share!

2 COMMENTS

LEAVE A REPLY

Recipe Rating




Please enter your comment!
Please enter your name here

Latest Recipes

The Very Best Double Chocolate Chocolate Chip Mint Cookies in the World

⇊ Jump to Recipe Chocolate Chocolate Chip Mint Cookies These...

Step by Step Instructions for Perfect Results: Julia Child’s Chocolate Cake

Jump to Recipe Julia Child chocolate cake Originally Posted 2009...

Why These Chocolate Peppermint Whoopie Pies are the Perfect Valentine’s Day Treat

⇩ Jump to Recipe chocolate peppermint whoopie pies Originally Posted...

This Chocolate Tuxedo Cream Cheesecake is Every Dessert You Love Combined Into One

Jump to Recipe blank Originally posted 2013 | Updated 2021

Adorable Mini Red Velvet Cakes Mean More of the Frosting You Love

Jump to Recipe blanks Original Post 2010| Updated 2021 

More Recipes Like This


It's Sweet to Share!