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Upside Down Pineapple Cake Recipe

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This classic upside-down pineapple cake features caramelized pineapple rings and maraschino cherries atop a moist, buttery vanilla cake. It’s a stunning retro dessert that’s surprisingly easy to make and always impresses guests.

Ingredients

Scale

For the Topping:

  • 1/4 cup unsalted butter, melted
  • 2/3 cup packed brown sugar (light or dark)
  • 1 can (20 oz) pineapple rings in juice, drained (reserve 1/4 cup juice)
  • 8-10 maraschino cherries, drained

For the Cake:

  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 2 large eggs, room temperature
  • 2 teaspoons pure vanilla extract
  • 1/2 cup buttermilk, room temperature
  • 1/4 cup reserved pineapple juice

Instructions

  1. Preheat and Prepare: Preheat your oven to 350°F (175°C). If using a cast iron skillet, there’s no need to grease it. If using a cake pan, lightly grease and line the bottom with parchment paper.
  2. Create the Topping: Pour melted butter into the bottom of your 10-inch cast iron skillet or cake pan. Sprinkle brown sugar evenly over the butter. Arrange pineapple rings in a single layer over the brown sugar (you should fit about 7-8 rings). Place a maraschino cherry in the center of each pineapple ring. Set aside.
  3. Mix Dry Ingredients: In a medium bowl, whisk together flour, baking powder, baking soda, and salt. Set aside.
  4. Cream Butter and Sugar: In a large bowl using an electric mixer, beat softened butter and granulated sugar on medium-high speed for 3-4 minutes until light and fluffy. This step incorporates air and creates a tender cake.
  5. Add Eggs and Vanilla: Beat in eggs one at a time, mixing well after each addition. Add vanilla extract and mix until combined. Scrape down the bowl sides as needed.
  6. Alternate Wet and Dry: With mixer on low speed, add the flour mixture in three additions, alternating with the buttermilk and pineapple juice (combined) in two additions. Begin and end with flour mixture. Mix just until combined – don’t overmix or you’ll develop too much gluten and create a tough cake.
  7. Assemble: Carefully spread the cake batter over the pineapple rings in the skillet, smoothing the top with a spatula. The batter will be thick – this is normal.
  8. Bake: Place skillet on a baking sheet (to catch any drips) and bake for 45-50 minutes, or until a toothpick inserted in the center comes out clean and the cake springs back when lightly pressed. The top should be golden brown.
  9. Cool Briefly: Remove from oven and let cool in the pan for exactly 10 minutes. This is crucial – cooling too long makes the topping stick, but flipping too soon means the topping will slide off.
  10. The Grand Flip: Run a knife around the edges of the cake to loosen it. Place your serving plate upside down over the skillet. Using oven mitts, hold both the plate and skillet firmly and quickly flip them over in one confident motion. Let the skillet rest on top for 1-2 minutes, then carefully lift it off. If any pineapple or cherries stick, simply replace them on the cake.
  11. Serve: Let the cake cool slightly before slicing, or serve warm with vanilla ice cream or whipped cream.

Notes

  • Don’t skip the parchment paper if using a regular cake pan – it helps with the flip.
  • Make sure your butter is truly softened (not melted) for the cake batter.
  • The 10-minute cooling time before flipping is critical for success.
  • If your brown sugar is clumpy, press it through a sieve before using.
  • Cake tastes even better the next day as flavors meld together.

Nutrition

Find it online: https://focialy.com/upside-down-pineapple-cake-recipe/