Pineapple Upside Down Cake

serves 8

Although vanilla extract works in this recipe, Keller prefers vanilla paste instead. Also, this recipe makes more "pan schmear" than needed, but it's difficult to make less. The remainder can keep in the refrigerator for several weeks or it can be frozen. Soften to room temperature before using. 

Pan Schmear

  • 8 tablespoons unsalted butter, at room temperature
  • 1½ tablespoons honey
  • ½ teaspoon dark rum
  • 1 cup packed light brown sugar
  • ¼ teaspoon pure vanilla extract (or vanilla paste)
  • kosher salt


  • 1 Gold (extra sweet) pineapple
  • 1⅓ cups cake flour
  • 2 teaspoons baking powder
  • 8 tablespoons unsalted butter, at room temperature
  • ½ cup plus 2 tablespoons granulated sugar
  • ½ teaspoon vanilla extract (or vanilla paste)
  • 2 large eggs
  • 1 tablespoon plus 1 teaspoon milk  (the batter was so thick I added a little more milk than this so I could spread it)

Preheat oven to 350 degrees F. 

Make the pan schmear:  In the bowl of a stand mixer fitted with the paddle attachment (or better yet, a Beater Blade paddle), combine the butter, honey, rum, brown sugar and vanilla.  Beat until smooth and well blended.

Spread ⅓ cup (I used ½ cup) of the mixture over the bottom of a 9-inch silicone cake pan (I used a regular 9-inch cake pan and sprayed it with Pam). Sprinkle lightly with salt.

Cut the top and bottom from the pineapple, and cut away the skin. Cut the pineapple lengthwise into quarters and cut the core from each section. Cut each piece crosswise into eighth inch slices. Beginning at the perimeter of the pan, make an overlapping ring of pineapple slices, curved sides facing out. Make a second ring inside the first one, overlapping the slices in the opposite direction, working toward the center. Reserve any remaining pineapple for other uses. 

Sift the flour and baking powder together; set aside. 

To make the batter: Using a stand mixer with the paddle attachment, mix the butter and sugar on low speed to combine. Beat on medium speed for about 3 minutes, until light and creamy, stopping to scrape down the sides as needed. Mix in the vanilla. Add the eggs one at a time, beating until the first one is incorporated before mixing in the second one. Scrape down the sides as needed. Beat in the milk. Add the flour mixture in 3 batches, beating just until combined. 

Pour the batter in the pan and spread over the pineapple. 

Bake for 15 minutes. Rotate the pan a half-turn for even browning and bake for another 20 to 25 minutes, until a cake tester or wooden toothpick inserted in the center of the cake comes out dry. Cool the cake, in the pan, on a rack for 20 to 30 minutes. 

Run a knife around the edges of the cake and invert on a serving platter. Serve warm. Leftover cake can be stored at room temperature for up to 2 days.  

** Serve this with vanilla ice cream or whipped cream or caramel sauce for added wow!

The Italian Dish