Holiday, Dessert, Gluten Free, Dairy Free, Summer

Pineapple Upside Down Cake

“I love Pineapple Upside Down Cake. Just saying.”

It was whispered to me at the far end of a dining table; we were celebrating my dear friend’s birthday for the first time in a week of planned parties. I had already made a chocolate sheet cake for that evening’s dessert, but filed the tropical information away for later use. I thought I might surprise her next year.

A few days later, in preparation for the second celebration, I asked her partner if there was anything I could bring to the party. “Well, if it isn’t too much to ask…”

If it were possible to interrupt someone via email, I would have. Of course! I’d say. Of course I’ll make a cake! Do you have a flavored request or might I tickle our birthday girl with a Pineapple Upside Down cake?

She wanted something in layers, with frosting, not the usual presentation for my imagined Pineapple cake. But, necessity is the mother of invention, and as we finished our conversation the dessert started to gestate in my head. Three layers of pineapple topped cake, but what about the frosting?

I took inspiration from the 1960’s addition of Maraschino cherries to Pineapple cakes and decided to try my hand at a sour cherry frosting/filling. Transportation would be an issue, the cake had to travel from Crown Heights to Chelsea. I decided to bring it disassembled, I’d beg for a few moments of privacy in their kitchen upon entering and stack the dessert there.

New York City: your radiating humidity can ruin the best laid plans. By the time I arrived at the party my frosting, whipped nicely in my apartment, was beginning to sweat and separate. Boor that I am, I kept my head down and pushed forward with the assembly. I layered the cakes without much difficulty, but by the time I had to frost the architecture, I was in trouble.

The cake was melting, light pink frosting oozing down the sides while the layers politely slid themselves into an unwelcomed impression of the Tower of Pisa. Ignoring all signs of distress, I straightened it out and shoved it in the refrigerator, praying a blast of cool air would temper its bad manners.

I was wrong. With a glass of rosé in hand I peaked into the icebox to find my cake slumped over and sad. Time for surgery. With a friend guarding the kitchen, I unstacked the layers, scraped out the filling, and restacked them. With no cherry frosting to lubricate their insides the Pineapple cakes stood tall. I reached for the container of extra frosting I left in the fridge and found it delightfully cool. With a quick whisk it was back in action and I frosted the outside of the cake. Repairs, as always, are messy, but this time proved successful. The cake was ready for candles.

And for the birthday girl: I never could have guessed that the lady sitting to my left on the first day of college (who inquired about Yom Kippur in the woods) would be such a gem. Keep sparkling.


  • 1 cup Sugar

  • ¼ cup Coconut Milk

  • 1 ½ cups sliced Pineapple

  • ½ cup Brown Rice Flour

  • ⅓ cup Tapioca Starch

  • ¼ cup+2 tablespoons White Rice Flour

  • 2 ½ teaspoons Baking Powder

  • ¾ teaspoon Salt

  • ¾ teaspoon Xanthan Gum

  • 3 Eggs

  • ¾ cup Sugar

  • ¾ cup Coconut Oil, melted and cooled

  • ¾ cup Coconut Milk

  • 1 teaspoon Almond Extract

Get Busy

  1. Heat your oven to 350 degrees.
  2. In a heavy saucepan heat the sugar over medium heat. Let it bubble and burble and brown itself. When it’s fragrant (it should smell like, duh, caramel) and dark, pour in the coconut milk. It will sputter and spatter. Let it simmer for a few minutes then remove it from the heat.
  3. Scatter the pineapple in the bottom of a parchment lined 9-inch springform pan. Pour the caramel over the fruit.
  4. Whisk together the dry ingredients.
  5. In a separate bowl, whisk together the sugar and eggs until they are pale yellow and slightly thickened.
  6. Add the oil, coconut milk, and almond extract, and whisk to combine.
  7. Add the dry ingredients to the wet mixture and stir until the batter comes together. Scrape the bottom of the bowl for pockets of rebel flour.
  8. Pour the cake batter into the cake pan, right on top of the fruit.
  9. Bake the cake for 40-50 minutes, or until a knife inserted into the center comes out clean.
  10. Remove the cake from the oven and let it cool for 10-15 minutes.
  11. Ready for the fun part? Run a knife around the edge of the cake. Put a plate (upside down) on top of the cake pan and flip everything over. Give it a shake, a tap, say a little prayer and lift off the cake pan. As thanks for liberation, the cake will give you a lovely pineapple steam facial. Don’t get your face too close. I don’t want to hear about burns.
  12. Eat it.

Prep. time: 15-20 minutes

Baking time: 45-55 minutes

Yield: 1 9-inch cake