Pineapple Upside Down Cake

It’s almost white pineapple season here in Hawaii and we can’t wait to use this new recipe from Christina Pun to unleash the magical combination of vanilla and pineapple. This cake is a piece of art inside and out. The combination of vanilla extract in the cake and vanilla bean paste in the topping transforms this sour delight with subtle aromas. This is a cake fit only for the finest vanilla on the block from Hawaiian Vanilla Company.




  • 1/3 cup (66 g) light brown sugar, lightly packed
  • 3 tablespoons unsalted butter
  • 2 teaspoons vanilla bean paste 
  • 1 ripe medium pineapple (about 3 lbs)



  • 8 tablespoons butter, at room temperature
  • ½ cup (100 g) granulated sugar 
  • ¼ cup (50 g) light brown sugar, lightly packed 
  • 2 teaspoons Hawaiian Vanilla Extract 
  • 2 eggs, at room temperature 
  • 1-1/2 cups (200 g) all-purpose flour 
  • 1-1/2 teaspoon baking powder
  • ¼ tsp kosher salt 
  • ½ cup whole milk, at room temperature 



Step 1 

Butter the sides and bottom of a 9” round cake pan, then line the bottom with parchment paper. Arrange the oven rack to the center position and preheat the oven to 350°F.


Step 2

In a saucepan, combine ½ cup light brown sugar, 3 tablespoons butter, 2 teaspoons vanilla bean paste, and a pinch of kosher salt. Cook over medium-low heat, stirring occasionally until the mixture is melted and smooth, and begins to bubble. Remove the pan from the heat and working quickly, pour the mixture into the prepared cake pan and swirl to evenly coat the bottom. Set aside and let cool.   


Step 3

Peel the pineapple, trimming off all the fibrous skin and removing any remaining “eyes”. Cut the pineapple in half lengthwise and again into quarters. Cut off the tough inner core from each quarter, then slice each quarter crosswise into 1/8” thick pieces. 


Step 4

Arrange the pineapple slices in the cake pan over the cooled topping. Overlap each piece slightly to create a tight pattern. Reserve any remaining pineapple for another use. 


Step 5

With an electric mixer on medium-high speed, cream together the remaining butter, brown sugar, and granulated sugar until light and fluffy, about 3 minutes. Scrape down the sides of the bowl. On medium speed, add the vanilla extract and beat in the eggs, one at a time, until smooth and fully incorporated.  


Step 6

In a separate bowl, whisk together the flour, baking powder, and salt. 


Step 7

With the mixer on low speed, gradually alternate adding the flour mixture and the milk in batches, beginning and ending with the flour mixture. Mix just until the batter comes together, being careful not to over-mix.  


Step 8 

Pour the cake batter over the pineapple slices and smooth the top with a spatula. Bake the cake for 35-40 minutes until the top is golden and the edges start to pull away from the sides of the pan.  The cake is ready when a wooden pick inserted in the center of the cake comes out clean. Let the cake cool in the pan for 15 minutes. 


Step 9 

Place a large serving platter over the top of the cake pan.  Using oven mitts, quickly flip to invert the cake onto the platter, then peel off the parchment paper. Serve the cake warm or at room temperature.  


Recipe created and photographed by Christina Pun.


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