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Classic Pineapple Upside-Down Cake

A golden, buttery classic bursting with caramelized pineapple flavor!
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Prep Time 20 minutes
Cook Time 40 minutes
Total Time 1 hour
Servings: 10 servings
Ingredients Equipment Method Notes

Ingredients
  

  • Caramelized Topping
  • 1/2 cup dark brown sugar, packed
  • 1/2 cup unsalted butter, softened
  • 1 can (20 oz) pineapple slices, drained
  • 1 jar Maraschino cherries (optional for garnish)
  • Cake Batter
  • 1 1/2 cup all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp salt
  • 1/2 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs, room temperature
  • 1 tsp vanilla extract
  • 1/2 cup pineapple juice (from the canned pineapple)

Equipment

  • Mixing bowls
  • Hand mixer or stand mixer
  • 9-inch cake pan or cast-iron skillet
  • Rubber spatula
  • Small saucepan (for butter/sugar mixture)
  • Measuring cups & spoons
  • Cooling rack

Method
 

  1. Preheat & Prep the Pan
    Preheat your oven to 350°F (175°C). Grease a 9-inch round or spring form cake pan or cast-iron skillet.
  2. Make the Caramelized Topping
    In a heated pot or skillet, mix the softened butter and dark brown sugar together until boiling. Spread evenly over the bottom of your prepared pan.
  3. Arrange the Pineapples
    Lay pineapple slices over the brown sugar mixture in a single layer.Place maraschino cherries in the center of each ring if desired.
  4. Prepare the Batter
    In a medium bowl, whisk together flour, baking powder, and salt. Set aside. In a separate large bowl, cream together the butter and sugar until light and fluffy.
  5. Add Wet Ingredients
    Beat in the eggs, one at a time, then add the vanilla extract.Pour in the pineapple juice and mix until smooth.
  6. Combine Dry & Wet Mixtures
    Gradually add the flour mixture to the wet ingredients, stirring until just combined.Don’t overmix — you want a soft, tender crumb.
  7. Pour Batter Over Pineapple Layer
    Carefully spread the cake batter evenly over the pineapple slices.
  8. Bake to Perfection
    Bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean.Let cool for about 10 minutes, then invert onto a serving plate while still warm.
  9. Serve & Enjoy
    Slice and enjoy this sweet, buttery cake that’s as stunning as it is delicious!Perfect for brunch, celebrations, or any moment that deserves a tropical touch. 🌺

Notes

  • Room temperature ingredients: Allow the butter and eggs to come to room temperature before baking. This helps the batter mix smoothly and creates a lighter, more tender crumb.
  • Pineapple choice: Canned pineapple slices are traditional and provide that classic, nostalgic flavor. Fresh pineapple rings can also be used, but be sure to slice them evenly for consistent baking.
  • Inverting the cake: Let the cake cool for about 10 minutes before flipping. Turning it out too soon may cause the topping to slide, while waiting too long can make it stick to the pan.
  • Extra moisture tip: For an even softer, bakery-style texture, add 2 tablespoons of sour cream or Greek yogurt to the batter.
  • Storage: Store leftover pineapple upside-down cake covered at room temperature for up to 2 days or refrigerate for up to 5 days. Warm individual slices slightly before serving for best flavor.
  • Serving suggestion: Serve warm with vanilla ice cream or whipped cream for a simple and elegant dessert.