This pineapple upside down cake is soft and buttery with a caramelized brown sugar pineapple & cherry topping.


Key Ingredients You Need

  • Baking Powder & Baking Soda: The two add plenty of lift under the heavy topping.
  • Salt: Balances the sweetness.
  • Creaming butter and sugar guarantees a buttery soft crumb. It’s how I prepare my vanilla cupcakes, too.
  • Sugar: White granulated sugar sweetens and tenderizes the cake. There’s brown sugar in the topping to provide essential flavor!
  • Vanilla Extract: Flavor.
  • Sour Cream: Along with cake flour and egg whites, sour cream promises a tender cake crumb. Plain yogurt works in a pinch.

Overview: How to Make the Best Pineapple Upside Down Cake

  1. Prepare the cake batter: Whisk the dry ingredients together. In a separate bowl, cream the butter and sugar together. You’ll have about 2 cups of cake batter and it’s very straightforward to prepare.
  2. Spread over topping: Pour and spread the cake batter over the chilled topping.
  3. Bake: Its juices will bubble up the sides, creating these incredible caramelized edges. With upside down cakes, it’s always good practice to place a baking pan or sheet on a lower rack to catch any juices should they splatter over the edges.

Ingredients

Topping

  • 1/4 cup (4 Tbsp; 56g) unsalted butter, melted
  • 1/2 cup (100g) packed light or dark brown sugar
  • 8–10 pineapple slices (see note)*
  • 15–20 maraschino cherries (see note)*

Cake

  • 1 and 1/2 cups (177g) cake flour (spooned & leveled)
  • 1 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 6 Tablespoons (85g) unsalted buttersoftened to room temperature
  • 3/4 cup (150g) granulated sugar
  • 2 large egg whites, at room temperature
  • 1/3 cup (80g) sour cream, at room temperature
  • 1 teaspoon pure vanilla extract
  • 1/4 cup (60ml) pineapple juice, at room temperature (use leftover from can)
  • 2 Tablespoons (30ml) milk, at room temperature

Instructions

  1. Preheat oven to 350°F (177°C).
  2. Prepare topping first: Pour 1/4 cup melted butter into an ungreased 9×2 inch pie dish or round cake pan. (Make sure the pan is 2 inches deep. Sprinkle brown sugar evenly over butter. Blot any excess liquid off the fruit with a clean towel or paper towel. Arrange about 6-7 blotted pineapple slices and all the cherries on top of the brown sugar. Place pan in the refrigerator for a few minutes as you prepare the cake batter. This helps solidify or “set” the topping’s arrangement.
  3. Make the cake batter: Whisk the cake flour, baking powder, baking soda, and salt together. Set aside.
  4. Scrape down the sides and up the bottom of the bowl with a rubber spatula as needed. Scrape down the sides and up the bottom of the bowl as needed. Pour the dry ingredients into the wet ingredients.
  5. Remove topping from the refrigerator. Pour and spread cake batter evenly over topping.
  6. Remove cake from the oven and cool on a wire rack for just 20 minutes. Invert the slightly cooled cake onto a cake stand or serving plate. Some of the juices from the topping will seep over the sides—that’s ok.
  7. Cover leftover slices and store for up to 3 days in the refrigerator or 3 months in the freezer. Thaw at room temperature. See make ahead instructions below.

Notes

  1. Make Ahead Instructions: You can refrigerate the topping in step 2 for up to 1 day.
  2. Special Tools (affiliate links): 9-inch Pie Dish or 9-inch Round Cake Pan | Glass Mixing Bowl | Whisk | Electric Mixer (Handheld or Stand) | Cooling Rack
  3. If you loved the old cake batter recipe, originally published in 2014, here it is: The topping recipe is the same. Prepare the recipe above through step 2. For the cake batter, whisk 1 and 2/3 cups (210g) all-purpose flour, 1/2 teaspoon baking powder, 1/4 teaspoon baking soda, and 1/2 teaspoon salt together. In a separate bowl, whisk 1/2 cup (115g) melted unsalted butter, 3/4 cup (150g) packed light brown sugar, 1/4 cup (50g) granulated sugar, 1 large egg, 1/4 cup (60g) yogurt or sour cream, 1/2 cup (120ml) milk, 1/4 cup (60ml) pineapple juice, and 1 Tablespoon vanilla extract together. Continue with step 5 in the recipe above.
  4. Pineapple & Cherries: Traditional recipes use canned pineapple and maraschino cherries. I recommend 1 20 ounce can of pineapple rings/slices, which usually holds 10 rings/slices. You can use fresh pineapple rings/slices and fresh cherries if desired. If using fresh cherries, I recommend halving them. Blot excess liquid off the fresh fruit just as I instruct in step 2.