Nana’s Kinda Pineapple Upside Down Cake

March 20, 2016
Pineapple Upside Down Cake

Much like myself, aesthetically, this cake was a flop. But, there’s no denying the power of its flavor. This cake is a combination of my grandma’s pineapple upside down cake and my compulsion for different textures and flavors. Maybe this is what my therapist meant when she said, “You’ll have to learn to give yourself whatever it was you felt like you got from your grandma.”

After slicing the pineapple, baking the layers, softening and spreading the dulce de leche, whipping the heavy cream…the last layer was just too much. The whole cake comes smashing down, making that ever comical farting sound; “pbbt.” The cake was too heavy for the delicate and straightforward whipped cream filling and as a result, caved in on itself and shrunk from a four layer cake to a three layer. It was a raggedy cake, but it sure tasted delicious.

My mom remembers a pineapple upside down cake my grandma made for her seven children on their birthdays. Of course, there was no recipe. I set out to recreate this cake and failed time after time. Creating the batter from scratch, obscene amounts of butter, aerating. Nothing would create a tender and sticky crumb. I found myself sitting on the floor of the local library, thumbing through vintage 1950s recipes, the 1969 Betty Crocker cookbook (the only cookbook my mother has) and Duncan Hines article snippets. Lightbulb moment. I had to go basic on this recipe. And so I settled on a combination of several factors, some straight out of the 1960s and some straight from my own imagination.

When I made this cake for my mom, I just made the plain pineapple upside down cake. I hit the nail on the head. She would not have liked this cocoa nib + Jacobsen sea salt version.

Nana’s Kinda Pineapple Upside Down Cake

Rating: 41

Prep Time: 2 hours

Cook Time: 35 minutes

Yield: 8-11 servings

The prep time is around 2 hours, but one hour of that is dedicating to the cooling of the cake. The other hour is dedicated to the slicing of the pineapple, caramel, whipping cream and assembly of the cake.


  • 1 small fresh pineapple, sliced into thin pieces
  • ________________________
  • 4 tb butter
  • 1/4 cup brown sugar
  • ________________________
  • 1 yellow cake mix
  • 4 eggs
  • 3/4 cup vegetable oil
  • 1 (3oz) box pineapple instant Jello pudding
  • 1 cup of 7 up
  • ________________________
  • 2 (13.4oz) cans of dulce de leche
  • chocolate covered cocoa nibs
  • 1 pint heavy cream
  • large flaked sea salt


  1. Preheat oven to 350 degrees.
  2. Add 2TB into each of your two 9'' cake pans and melt in the oven.
  3. Pour your cake mix, pudding mix, eggs, oil and soda into a large mixing bowl and mix for about 1 minute.
  4. You should hear your butter sizzling, take the pans out of the oven and sprinkle 2TB of brown sugar in one pan and 2TB in the other; with a fork combine the sugar and butter.
  5. Line the thinly sliced pineapple pieces onto the caramel, ensuring the entire bottom of the pan is covered.
  6. Pour equal parts batter into each pan, over the pineapple, and bake for about 30-35 minutes or until a toothpick inserted comes out clean.
  7. Set on cooling racks until fully cooled.
  8. Whip your cream until it's a thick (but not curdled looking) viscosity; should be able to stand on its own.
  9. Place cake layer on cake stand and cut one layer in half. Repeat for other layer. Now, you'll have four layers.
  10. In a microwave safe container, warm dulce de leche in the microwave for about 10-20 seconds.
  11. Place one bottom layer (without pineapple) on cake stand, spread dulce de leche onto cake layer. Sprinkle course sea salt and cocoa nibs over dulce de leche. Pipe whipped cream over dulce de leche and nibs. Place a top layer with pineapple on to the whipped cream. Dulce de leche. Salt and nibs. Pipe cream. Layer without pineapple. Dulce de leche. Salt and nibs. Pipe cream. Should finish with the last layer with pineapple.


You could turn this into a two-day task. Bake the cakes and then assemble the next day.

I tried using canned pineapple in 100% pineapple juice. It was awful. The pineapple was just too pale and saturated. It wouldn't caramelize at all. Spring an extra couple of bucks and purchase a fresh pineapple.

If you cannot find pineapple insant pudding, use vanilla.



  • Reply Christina March 22, 2016 at 3:50 am

    Illyanna!!!! Will you make this for me for my Birthday??? Hmmmmmmmm……

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      Reply Eat Gorda Eat March 24, 2016 at 1:42 am

      Of course! I’d be happy to.

  • Reply Eli Med August 26, 2016 at 6:56 pm

    You’re right: This is aesthetically abominable. I suggest that you redeem yourself and bake it again in my apartment this weekend; actually tonight. I will help with the aesthetics. You take care of the bake stuff. We could eat together; but more for me, please.

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      Reply Eat Gorda Eat August 26, 2016 at 7:02 pm

      I am gonna make it again, but for my boss’ birthday. In December.

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