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Classic Pineapple Upside-Down Cake

Classic Pineapple Upside-Down Cake

This classic pineapple upside-down cake features a glossy brown-sugar caramel topping with pineapple rings and cherries and a tender, buttery cake beneath. It takes about 20 minutes to prepare and bakes in about 45 minutes, and is best served warm or at room temperature with ice cream or whipped cream.
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Prep Time:20 minutes
Cook Time:50 minutes
Total Time:1 minute
Course: Desserts
Keyword: brown-sugar caramel, pineapple, upside-down cake

Equipment

  • ▢9-inch cake pan with 2-inch side, or 9 or 10-inch cast-iron skillet

Ingredients

  • 6 tablespoon unsalted butter melted
  • 2/3 cup light brown sugar
  • 8 pineapple rings canned or fresh
  • Maraschino cherries
  • 13/4 cup all-purpose flour sifted
  • 11/2 teaspoon baking powder
  • 1/4 teaspoon Kosher salt
  • 3/4 cup unsalted butter 1½ sticks, softened
  • 1 cup sugar
  • 2 large eggs
  • 1/4 cup pineapple juice
  • 1 tablespoon vanilla extract
  • 1/2 cup whole milk

Instructions

  1. Pour the melted butter into a 9-inch cake pan or cast-iron skillet.
  2. Evenly sprinkle the light brown sugar over the melted butter, then arrange the pineapple rings on top and place Maraschino cherries in the centers of the rings and in any open spaces.
  3. Preheat the oven to 350°F.
  4. In a medium bowl, whisk together the all-purpose flour, baking powder, and Kosher salt; set aside.
  5. In a large mixing bowl using a stand mixer or hand mixer, cream the sugar with the softened unsalted butter on medium until slightly fluffy and pale in color, about 3 to 4 minutes, scraping down the sides of the bowl as needed.
  6. Whisk in the eggs, pineapple juice, and vanilla extract until combined.
  7. With the mixer running on low, add half of the flour mixture, mix until incorporated, then add half of the milk. Repeat with the remaining flour and milk and mix until fully combined; the batter will be somewhat thick.
  8. Use a spatula to transfer the batter into the prepared pan and gently spread it evenly over the pineapple rings and cherries.
  9. Bake until a toothpick inserted into the center comes out clean, about 45 minutes.
  10. Let the cake rest for 10 minutes, then carefully invert the cake onto a cake stand or serving plate.
  11. Slice and serve warm or at room temperature; optionally serve with ice cream or whipped cream.

Notes

Notes
If using fresh pineapple, you'll need to purchase extra pineapple juice. Most canned pineapple slices are filled with 100% pineapple juice.
A cast-iron skillet is traditional, but we find a 9-inch cake pan with 2-inch sides works just as well, and is much easier to invert and release the cake onto a platter.
The batter is fairly thick and will require a spatula or the back of a large spoon to help the batter out of the mixing bowl and to spread evenly over the pineapples and cherries.
Maraschino cherries can be found in the canned fruit section of your grocery store, or in the adult beverage condiment section.
Insert a toothpick into the cake when the baking time is finished. If no batter sticks to the toothpick when removed from the cake, it's ready. If there is wet batter (not cake crumbs), then bake for another 5 to 10 minutes, and re-try the toothpick check. Once no wet batter is stuck to the toothpick, the cake is ready.
We find the cake is best served warm, soon after baking. But can also easily be briefly reheated in the microwave when serving the next day. It's also delicious at room temperature.