Modern Fresh Pineapple Upside Down Cake


This slice of Fresh Pineapple Upside Down cake looks pretty unassuming, but don’t be fooled. It’s really good. Moist without being wet. Sweet without being cloying. And not crazy fattening either.

I always imagined Pineapple Upside Down Cake was something that would be found in a Betty Crocker cookbook, alongside Beef Stroganoff and Baked Alaska. Delicious but dated. This recipe is an updated take on the old classic. No boxed cake mix, obviously. But most importantly, it uses fresh pineapple. This recipe was adapted from the one on the Epicurious website.


1 2/3 (7 oz) cups all-purpose flour
1 1/2 tsp baking powder
1/4 tsp baking soda
1/4 tsp salt
1/2 fresh pineapple, halved lengthwise, cored, and peeled
1 1/2 sticks (3/4 cup) unsalted butter, softened
1/2 cup (3.5oz) packed light brown sugar
2/3 cup (4.7oz) granulated sugar
1 tsp pure vanilla extract
2 large eggs
2/3 cup well-shaken buttermilk


  1. Put oven rack in middle position and preheat to 350°F.
  2. Sift together flour, baking powder and soda, and salt. Set aside.
  3. Next, cut pineapple crosswise into 1/4-inch-thick wedges.
  4. Using a 1/2 stick of butter, grease a 9″ round (2″ deep) cake pan, lightly coat the sides of the pan and generously on the bottom.
  5. Then, evenly sprinkle the brown sugar atop the butter.
  6. Starting in the center, overlap the pineapple slices slightly.
  7. Beat together remaining stick of butter, granulated sugar, and vanilla at medium speed until light and fluffy, about 2 minutes.
  8. Add 1 egg at a time, beating well after each addition.
  9. Reduce speed to low and add flour mixture alternately with buttermilk in batches. Begin and end with flour and mix just until batter is smooth.
  10. Spread batter evenly over pineapple and bake until a wooden pick inserted in center of cake comes out clean, 40 to 45 minutes.
  11. Cool 15 minutes in pan on a rack.
  12. Invert cake onto a plate and remove pan.
  13. Cool to room temperature.

This Fresh Pineapple Upside Down Cake serves 10 people.
Approximately 329 calories per slice.

1 thought on “Modern Fresh Pineapple Upside Down Cake”

  1. Elizabeth DiPalma

    I made this for a party on the 4th. We left before people were done noshing, and I left the cake (hoping that there would be some left when I came back to get my plate & server). Silly me! The host had polished off the last piece for breakfast, and he summed it up: “I don’t usually like this kinda thing, but boy was it good!!”

    So now I have to make another one, having limited myself to one piece at the ‘do’. It’s amazing. The cake transcends the genre, and fresh pineapple just sings! Thanks, Sue!

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