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A delicious pineapple upside down cake on a white serving plate, topped with caramelized pineapple rings and cherries, with one slice cut.
Daniel

Classic Buttery Pineapple Upside-Down Cake

A timeless dessert featuring a caramelized brown sugar and pineapple topping with a moist, buttery vanilla cake. This classic pineapple upside-down cake is a guaranteed crowd-pleaser.
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Prep Time 20 minutes
Cook Time 45 minutes
Total Time 1 hour 5 minutes
Servings: 8 servings
Course: Dessert
Cuisine: American
Calories: 420
Ingredients Equipment Method Notes

Ingredients
  

For the Topping
  • 1/2 cup unsalted butter melted (1 stick or 113g)
  • 3/4 cup packed light brown sugar (150g)
  • 1 can (20 oz) pineapple rings in juice drained, reserve 1/4 cup of juice
  • 8-10 maraschino cherries stems removed
For the Cake Batter
  • 1 1/2 cups all-purpose flour (180g)
  • 2 tsp baking powder
  • 1/4 tsp salt
  • 1/2 cup unsalted butter softened to room temperature (1 stick or 113g)
  • 3/4 cup granulated sugar (150g)
  • 2 large eggs room temperature
  • 1 tsp vanilla extract
  • 1/2 cup whole milk room temperature
  • 1/4 cup reserved pineapple juice from the can, room temperature

Equipment

  • 9-inch Round Cake Pan
  • Mixing Bowls
  • Electric Mixer

Method
 

Prepare the Pan and Topping
  1. Preheat your oven to 350°F (175°C). Use a 9-inch round cake pan (not a springform pan). Do not grease the pan.
  2. Pour the melted butter for the topping into the bottom of the cake pan and tilt to coat it evenly.
  3. Sprinkle the light brown sugar evenly over the melted butter.
  4. Arrange the drained pineapple rings in a single layer over the brown sugar. Place a maraschino cherry in the center of each pineapple ring and in any gaps between them.
Make the Cake Batter
  1. In a medium bowl, whisk together the all-purpose flour, baking powder, and salt. Set aside.
  2. In a large bowl, using an electric hand mixer or a stand mixer with a paddle attachment, beat the softened butter and granulated sugar on medium-high speed until light and fluffy, about 3-4 minutes.
  3. Add the eggs one at a time, beating well after each addition. Scrape down the sides of the bowl, then beat in the vanilla extract.
  4. In a liquid measuring cup, combine the room temperature milk and the 1/4 cup of reserved pineapple juice.
  5. With the mixer on low speed, add the dry ingredients in three additions, alternating with the milk mixture in two additions (Dry, Wet, Dry, Wet, Dry). Mix just until combined and be careful not to overmix.
Bake and Invert the Cake
  1. Carefully spoon the batter over the pineapple layer in the pan. Use an offset spatula to spread it evenly to the edges.
  2. Bake for 40-45 minutes, or until a wooden skewer or toothpick inserted into the center of the cake comes out clean.
  3. Remove the cake from the oven and place the pan on a wire rack to cool for exactly 10 minutes. Do not cool for longer, or the caramel may solidify and stick to the pan.
  4. Run a thin knife around the edge of the cake to loosen it from the pan. Place a large, flat serving platter upside down over the top of the cake pan.
  5. Using oven mitts, carefully and quickly flip the pan and platter over together. Let the pan sit for a minute before slowly lifting it off. If any pineapple slices stick to the pan, gently remove them and place them back on top of the cake.
  6. Serve the pineapple upside-down cake warm or at room temperature.

Notes

Tips for Success: Using room temperature ingredients (butter, eggs, milk) is crucial for a smooth batter and a tender cake crumb. Make sure to invert the cake after exactly 10 minutes of cooling for a perfect release.
Storage: Store leftover cake covered at room temperature for up to 2 days or in the refrigerator for up to 4 days. Gently rewarm slices in the microwave if desired.