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Pineapple Upside Down Cake baking in the oven, golden and rising beautifully.

Pineapple Upside Down Cake: A Classic Dessert Favorite


  • Author: Emma
  • Total Time: 55 minutes
  • Yield: 1 (9-inch) cake 1x

Description

This Pineapple Upside Down Cake is a timeless, buttery classic with a caramelized pineapple topping, juicy cherries, and a soft, moist cake. Perfect for any occasion, this easy-to-make cake delivers a sweet, slightly tangy flavor that melts in your mouth. Whether you’re making it for a holiday, a birthday, or a weekend treat, this retro dessert never goes out of style! Serve it warm with ice cream or enjoy it chilled for a firmer bite.


Ingredients

Scale

For the Caramelized Topping:

  • ¼ cup unsalted butter (melted)
  • ¾ cup packed brown sugar
  • 1 (20 oz) can pineapple slices (drained, juice reserved)
  • 1012 maraschino cherries (optional, for decoration)

For the Cake Batter:

  • 1 ½ cups all-purpose flour
  • 1 cup granulated sugar
  • ½ cup unsalted butter (softened)
  • 2 large eggs
  • ½ cup pineapple juice (from the can)
  • 1 teaspoon vanilla extract
  • 1 ½ teaspoons baking powder
  • ½ teaspoon baking soda
  • ¼ teaspoon salt
  • ½ cup whole milk

Instructions

Step 1: Prepare the Topping

  1. Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan or cast iron skillet.
  2. Pour melted butter into the pan and spread evenly.
  3. Sprinkle brown sugar over the butter.
  4. Arrange pineapple slices in a single layer over the sugar.
  5. Place a maraschino cherry in the center of each pineapple slice.

Step 2: Make the Cake Batter

  1. In a large bowl, cream butter and sugar until light and fluffy.
  2. Add eggs one at a time, beating well after each addition.
  3. Mix in vanilla extract and pineapple juice.
  4. In another bowl, whisk together flour, baking powder, baking soda, and salt.
  5. Alternately add the dry ingredients and milk to the wet mixture, mixing until just combined.

Step 3: Bake the Cake

  1. Pour the batter over the pineapple layer, spreading evenly.
  2. Bake for 35-40 minutes, or until a toothpick inserted in the center comes out clean.
  3. Let cool for 5 minutes before flipping onto a serving plate.

Step 4: Flip and Serve

  1. Place a serving plate over the pan, hold firmly, and flip in one smooth motion.
  2. Let cool for 10 minutes before slicing. Serve warm or at room temperature.

Notes

  • Make It Extra Caramelized: Bake the topping in the pan for 5 minutes before adding the batter.
  • Gluten-Free Version: Use a 1:1 gluten-free flour blend.
  • Dairy-Free Alternative: Swap butter for vegan butter and milk for almond milk.
  • Storage:
    • Room Temperature: 1-2 days (loosely covered).
    • Refrigerate: Up to 5 days (airtight container).
    • Freeze: Wrap slices tightly and freeze for up to 3 months.
  • Prep Time: 15 minutes
  • Cook Time: 40 minutes
  • Cuisine: American / Retro Classic

Nutrition

  • Calories: ~320 kcal
  • Fat: ~12g
  • Carbohydrates: ~50g
  • Fiber: ~1g
  • Protein: ~3g