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Pineapple Upside Down Cake Recipe

A timeless classic, this Pineapple Upside Down Cake Recipe features caramelized brown sugar, juicy pineapple rings, and a tender vanilla-infused crumb—perfect for celebrations or a sweet everyday treat.
Prep Time 20 minutes
Cook Time 45 minutes
Course Dessert
Cuisine American
Servings 8
Calories 350 kcal

Ingredients
  

Topping

  • ½ cup 115 g unsalted butter, melted
  • cup 135 g packed light brown sugar
  • 8 –10 pineapple rings fresh or canned, drained if canned
  • 8 –10 maraschino cherries patted dry

Cake Batter

  • cups 220 g all-purpose flour
  • 2  tsp baking powder
  • ¼  tsp fine sea salt
  • ½  cup 115 g unsalted butter, softened
  • 1  cup 200 g granulated sugar
  • 2  large eggs room temperature
  • 2  tsp pure vanilla extract
  • ½  cup 120 ml whole milk, room temperature
  • ¼  cup 60 ml pineapple juice

Instructions
 

Preheat & prep pan:

  • Preheat oven to 350°F (175°C). Place a 9‑inch round cake pan in the center rack.

Make caramel topping:

  • Pour melted butter into the pan, sprinkle brown sugar evenly over it, and tilt to combine.

Arrange fruit:

  • Lay pineapple rings atop the caramel, then nestle a cherry in each ring’s center.

Mix dry ingredients:

  • Whisk flour, baking powder, and salt in a medium bowl.

Cream butter & sugar:

  • In a large bowl, beat softened butter and granulated sugar until pale and fluffy (3–4 minutes).

Add eggs & vanilla:

  • Beat in eggs one at a time, then stir in vanilla extract.

Combine batter:

  • Alternately add dry mixture and milk–pineapple juice mix in three additions, beginning and ending with flour. Mix until just combined.

Bake:

  • Pour batter over fruit, smooth the top, and bake 40–45 minutes, or until a toothpick comes out clean.

Cool & invert:

  • Let cake rest in pan 10–15 minutes. Place a serving plate over the pan, flip to release, and let cool slightly before slicing.

Notes

  • Room‑temperature ingredients ensure even mixing and tender crumb.
  • Prevent sticking by lightly greasing and flouring the pan’s sides if not nonstick.
  • Flavor variations: Add ½ cup shredded coconut or 1 Tbsp bourbon to the pineapple rings.
  • Storage: Store covered at room temperature up to 2 days or refrigerated up to 5 days. Freeze tightly wrapped up to 2 months.
  • Mini cakes: Divide topping and batter into 4‑inch ramekins; bake 20–25 minutes.