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Classic Pineapple Upside Down Cake – Sweet, Nostalgic, and Perfectly Moist

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This classic pineapple upside down cake features caramelized pineapple rings and maraschino cherries atop a tender, buttery cake. Beautifully nostalgic and surprisingly easy to make, it’s the perfect retro dessert for any occasion!

Ingredients

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For the Topping:

  • ¼ cup (½ stick) unsalted butter, melted
  • ½ cup packed light brown sugar
  • 7-8 canned pineapple rings (from a 20 oz can), well drained
  • 7-8 maraschino cherries, drained and patted dry
  • 2 tablespoons reserved pineapple juice

For the Cake:

  • ½ cup (1 stick) unsalted butter, softened to room temperature
  • ¾ cup granulated sugar
  • 2 large eggs, at room temperature
  • 1½ teaspoons pure vanilla extract
  • 1½ cups all-purpose flour
  • 1½ teaspoons baking powder
  • ¼ teaspoon salt
  • ½ cup whole milk, at room temperature
  • ¼ cup reserved pineapple juice

Instructions

  • Preheat and prepare: Preheat your oven to 350°F (175°C). If using a cake pan, grease it well with butter or cooking spray. If using a cast iron skillet, make sure it’s clean and dry (no need to grease cast iron).
  • Make the topping: Pour the ¼ cup melted butter into the bottom of your 9-inch or 10-inch pan, tilting to coat evenly. Sprinkle the brown sugar evenly over the melted butter. Drizzle 2 tablespoons of reserved pineapple juice over the brown sugar. Arrange the pineapple rings in a single layer over the brown sugar mixture—you should fit about 7 rings in a 9-inch pan, slightly overlapping if needed. Place a maraschino cherry in the center of each pineapple ring and in any gaps between rings for a beautiful presentation. Set the pan aside.
  • Cream butter and sugar: In a large mixing bowl, using an electric mixer on medium-high speed, beat the softened ½ cup butter and granulated sugar together for 3-4 minutes until light, fluffy, and pale in color. This incorporates air and creates a tender cake. Scrape down the sides of the bowl as needed.
  • Add eggs and vanilla: Add the eggs one at a time, beating well after each addition until fully incorporated. The mixture should look smooth and creamy. Beat in the vanilla extract.
  • Combine dry ingredients: In a medium bowl, whisk together the flour, baking powder, and salt until evenly combined.
  • Mix wet ingredients: In a small bowl or measuring cup, combine the ½ cup milk with ¼ cup reserved pineapple juice. Stir to mix.
  • Alternate adding dry and wet: With the mixer on low speed, add the flour mixture to the butter mixture in three additions, alternating with the milk mixture in two additions. Start and end with flour. Mix each addition just until combined—don’t overmix! The batter should be smooth and slightly thick. Scrape down the sides and bottom of the bowl to ensure everything is incorporated.
  • Assemble and bake: Carefully pour the cake batter over the arranged pineapple rings in the pan, spreading gently and evenly with a spatula to cover all the fruit. The batter will be thick—take your time spreading it into an even layer without disturbing the fruit arrangement too much.
  • Bake: Place the pan on the center rack of your preheated oven and bake for 40-50 minutes (40 minutes for 10-inch pan, 45-50 minutes for 9-inch pan). The cake is done when the top is golden brown, springs back when lightly touched, and a toothpick inserted into the center comes out clean or with just a few moist crumbs. If you’re using a cast iron skillet, it may take a few extra minutes since the pan is heavier.
  • Cool briefly: Remove from the oven and place the pan on a cooling rack. Let the cake cool in the pan for 5-10 minutes—no longer! If it cools too much, the caramelized sugar will harden and make it difficult to unmold.
  • Flip and reveal: Run a knife carefully around the edges of the cake to loosen it. Place your serving plate upside down over the top of the pan. Using oven mitts or thick towels (the pan is still hot!), hold the plate and pan together firmly and quickly flip them over in one confident motion. Leave the pan in place for a minute to let the caramel drip down, then carefully lift the pan away. If any pineapple or cherries stick to the pan, simply remove them and place them back on the cake—the warm caramel will hold them in place.
  • Serve: Let the cake cool for at least 15-20 minutes before slicing, or serve warm. The cake is delicious warm, at room temperature, or even chilled!

Notes

  • Drain fruit thoroughly: Excess moisture from the pineapple and cherries can make the cake soggy. Pat them dry with paper towels before arranging.
  • Don’t skip the flip timing: Flip the cake after 5-10 minutes of cooling. If you wait too long, the caramelized sugar hardens and makes unmolding difficult.
  • Pan size matters: A 9-inch pan creates a taller cake, while a 10-inch pan makes a slightly thinner cake. Both work beautifully—adjust baking time accordingly.
  • Room temperature ingredients: Make sure butter, eggs, and milk are at room temperature for the smoothest batter and best texture.

Nutrition

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