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Slice of moist pineapple upside-down cake topped with caramelized pineapple rings and cherries on a white plate.

Easy Pineapple Upside-Down Cake

This classic Easy Pineapple Upside-Down Cake features a sweet caramelized pineapple and cherry topping baked directly onto a moist, tender vanilla cake. It's surprisingly simple to make and always a showstopper!
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Prep Time 20 minutes
Cook Time 35 minutes
Total Time 55 minutes
Servings: 8 slices
Course: Dessert
Cuisine: American
Calories: 380
Ingredients Equipment Method Notes

Ingredients
  

For the Topping
  • 1/2 cup unsalted butter melted
  • 1 cup light brown sugar packed
  • 1 20 oz can pineapple rings drained, juice reserved
  • 10-12 maraschino cherries drained, stemmed
For the Cake Batter
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter softened
  • 1 cup granulated sugar
  • 2 large eggs room temperature
  • 1 teaspoon vanilla extract
  • 1/2 cup milk room temperature
  • 1/4 cup reserved pineapple juice

Equipment

  • 9-inch round cake pan
  • Large mixing bowl
  • Medium mixing bowl
  • Electric mixer (handheld or stand)
  • Small Saucepan
  • Whisk
  • Spatula
  • Wire Rack
  • Serving plate/platter
  • Oven Mitts

Method
 

Prepare the Topping
  1. Preheat your oven to 350°F (175°C).
  2. Melt the 1/2 cup of butter directly in a 9-inch round cake pan over low heat on the stovetop, or melt separately and pour into the pan. Tilt the pan to evenly coat the bottom.
  3. Evenly sprinkle the 1 cup of packed light brown sugar over the melted butter in the pan.
  4. Arrange the drained pineapple rings over the brown sugar mixture. For a classic look, place one ring in the center and arrange the others around it.
  5. Place one maraschino cherry in the center of each pineapple ring and scatter any remaining cherries in the gaps between the rings.
Prepare the Cake Batter
  1. In a medium bowl, whisk together the all-purpose flour, baking powder, and salt. Set aside.
  2. In a large mixing bowl, using an electric mixer, cream together the 1/2 cup softened unsalted butter and 1 cup granulated sugar until light and fluffy (about 2-3 minutes).
  3. Beat in the large eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  4. In a separate small bowl, combine the 1/2 cup milk and 1/4 cup reserved pineapple juice.
  5. With the mixer on low speed, gradually add the dry ingredients to the wet ingredients in three additions, alternating with the milk and pineapple juice mixture, beginning and ending with the dry ingredients. Mix until just combined and smooth; do not overmix.
Assemble and Bake
  1. Carefully spoon the cake batter evenly over the pineapple and cherry topping in the prepared cake pan. Gently spread it to the edges, being careful not to disturb the fruit arrangement too much.
  2. Bake for 35-40 minutes, or until a wooden skewer or toothpick inserted into the center of the cake comes out clean.
  3. Once baked, remove the cake from the oven and let it cool in the pan on a wire rack for only 5 minutes. This brief cooling period helps the topping set slightly but prevents it from sticking.
  4. Place a large serving plate or platter upside-down over the cake pan. Carefully, using oven mitts, invert the cake pan and plate together, so the cake flips onto the serving platter.
  5. Lift the cake pan off the cake. If any fruit sticks to the pan, gently re-place it onto the cake.
  6. Allow the cake to cool completely before slicing and serving.

Notes

For best results, ensure your butter, eggs, and milk are at room temperature for a smoother batter.
If you don't have pineapple juice from the can, you can substitute with water or milk.
This cake is best served warm or at room temperature. Leftovers can be stored covered at room temperature for up to 2 days or refrigerated for up to 4 days.
Consider adding a scoop of vanilla ice cream or a dollop of whipped cream when serving warm.