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Pineapple Upside-Down Cake

Yield: One 10” Cake Round

Degree of difficulty: Easy

Prep Time: 20 minutes

Bake Time: 35 - 40 minutes

Total Time: 55 minutes – 1 hour


Brown Sugar Mix:

3 tablespoons (42 g) Unsalted butter, room temperature
¾ teaspoons (5 g) Honey
½ teaspoon (3 g) Dark rum
1/3 cup (72 g) Dark brown sugar
¼ teaspoon (2 g) Vanilla extract
¼ teaspoon (1 g) Kosher salt

1 ea 20 oz. Can pineapple rings
1 ea 6 oz. Jar Amarena or Maraschino Cherries, stemmed

Vegetable oil spray


Cup4Cup Yellow Cake:

1 ¼ cups (175 g) Cup4Cup multipurpose flour
1 ¼ teaspoon (4 g) Baking powder
½ teaspoon (2 g) Baking soda
½ teaspoon (2 g) Kosher salt
2 each (100 g) Large eggs
1 cup (200 g) Granulated sugar
1 teaspoon (5 g) Vanilla extract
½ cup (110g) Vegetable oil
½ cup (105g) Buttermilk
5 drops Yellow food coloring (optional)


  1. Preheat the oven to 350°F.
  2. Line the bottom of a 10” round cakepan with parchment paper and spray with vegetable oil spray.
  3. Remove the pineapple rings from the can and pat dry with paper towels.
  4. Place rings of pineapple in a single layer on the bottom of the lined cakepan. There should be 6 rings along the perimeter and 1 in the center.
  5. Place cherries in the centers of the pineapple rings and in the voids between the pineapple rings.
  6. Prepare the Brown Sugar Mix Recipe:
  7. In the bowl of an electric mixer with a paddle attachment, combine the ingredients for the brown sugar mix and mix on medium-low speed until the mixture is homogenous.
  8. Finely crumble and spread the brown sugar mix evenly distributing it around the cakepan over the pineapple rings.
  9. Prepare the Yellow Cake Recipe:
  10. In a large bowl, combine all the dry ingredients for the yellow cake recipe except for the sugar.
  11. In the bowl of a stand mixer with a paddle attachment, cream the eggs and sugar for the yellow cake recipe on medium speed until the sugar is dissolved.
  12. Stream in the oil and vanilla for the yellow cake recipe until incorporated.
  13. Reduce mixer speed to medium-low, gradually add in half of the flour mixture. Once incorporated, stream in half the buttermilk and mix until homogenous. Repeat both additions with the remaining halves. Optional, add yellow food coloring and mix until the color and texture are uniform.
  14. Scrape down the sides and bottom of the bowl and mix for 20 seconds.
  15. Pour the cake batter directly onto the pineapple and sugar mixture. Gently spread the batter so that the pineapples stay in their designated places, but the batter is evenly distributed.
  16. Bake until a toothpick inserted in the center comes out clean, about 35-40 minutes. If the top starts to darken too much, without touching the cake, lay a piece of foil over the top of the cake for the duration of the bake.
  17. Once the cake is cooked through, run a knife along the edge of the cake pan releasing the cake from the pan.
  18. Using a cutting board or baking sheet, cover the top of the cake and invert onto the cutting board or sheet pan, then remove the cakepan and parchment paper. Allow the cake to cool before serving.