Pineapple Upside Down Cake

Pineapple Upside Down Cake

When Mr. RC requested pineapple upside down cake for his birthday, I of course had to oblige (wifely duties call). It's one of our favorite cakes, what with the moist dough and the crunchy, caramel topping. But, per usual, I can never let a good recipe just be (whoever said "Don't mess with a good thing!" clearly hadn't met me) so this time I was determined to find a few ways to switch up the old pineapple upside down cake recipe and make it into something just a little more special. So I added lots of coconut flavors (because have you been to a tropical island?! Pineapple and coconut were just meant to be together.. obvs!) and I baked it in a skillet (because everything tastes better in a skillet, double obvs). The results? One happy birthday boy and one clean cake pan. I knew there was a method to my recipe changing madness...



serves 8




  • 1/4 cup butter
  • 1/2 cup light brown sugar, firmly packed
  • 1/4 teaspoon ground cinnamon
  • 1/4 teaspoon ground ginger
  • 20-ounce can pineapple rings in juice, drained (reserve juice for the cake)


  • 3 tablespoons butter
  • 1/4 cup brown sugar
  • 1/2 cup white sugar
  • 1 large egg
  • 1/2 teaspoon salt
  • 1 3/4 teaspoons baking powder
  • 1 teaspoon vanilla extract
  • 1 1/3 cups all-purpose flour
  • 1/4 cup coconut milk
  • 1/4 cup pineapple juice (reserved from the rings)


  • 1 can of full-fat coconut milk, chilled
  • Sugar, to taste


  1. Preheat oven to 375 degrees.

  2. Next, you will prepare the topping. In a 10-12 inch cast iron skillet set over a burner on medium heat, add all of the topping ingredients, minus the pineapple rings (butter, brown sugar, cinnamon, and spices). Cook, stirring constantly, until the butter has melted, everything has combined and the mixture begins to bubble, about 3-5 minutes. Turn the burner off. Lay the pineapple rings on top of the brown sugar mixture (7 rings fit in the pan I used), then set the pan aside.

  3. To make the cake, begin by creaming together the butter and sugars in the bowl of stand mixer. Next, beat in the egg, salt, baking powder and vanilla. Lastly, alternate adding in the flour with the liquids (pineapple juice and coconut milk), making sure to not over mix.

  4. Pour the cake batter over the pineapple rings. The batter is really thick so you will definitely need a spatula to help spread it around. Also, don't be worried if the pineapple is showing through the batter or if it barely covers the pan. It will spread out and rise as it bakes.

  5. Bake the cake for 18-30 minutes (depends on your oven and the size of the pan you used....mine was a 12 inch skillet so it only took 18 minutes to bake), or until a toothpick inserted into the middle comes out clean.

  6. Once the cake is done, remove it from the oven and let it cool for 15-20 minutes. Then, gently run a knife around the edge, place a serving plate on top, grasp the plate and the pan with both hands and flip it over. Gently tap the bottom of the pan all over, then slowly lift the pan off, using your knife to help loosen anything that might be stuck.

  7. To make the coconut whipped cream, open your can of coconut milk and separate the thick cream part from the watery liquid. Place the thick cream in a mixing bowl and begin beating it on medium-high speed. Add in as little or as much sugar as you would like. I don't like things overly sweet so I only used about 2 tablespoons. Continue whipping for a few minutes, until soft peaks form. Please note: unlike traditional whipped cream, this doesn't stay stiff forever. As it warms up, it will begin to thin slightly, but simply placing it back in the fridge will get it nice and thick again. It also tastes great thinned out, so if you don't feel like re-whipping it, don't worry!

  8. Serve the cake warm with a dollop of coconut cream. Store remaining coconut cream in an airtight container in the fridge. The cake should be tightly wrapped with plastic wrap and will last about 2 days on the counter, or about 4-5 days if stored in the fridge.