Classic Pineapple Upside-Down (Printable Version)

Golden vanilla cake topped with caramelized pineapple and cherries for a stunning dessert.

# What You Need:

→ Topping

01 - 1/4 cup unsalted butter
02 - 3/4 cup packed light brown sugar
03 - 8 to 10 canned pineapple rings, drained
04 - 8 to 10 maraschino cherries

→ Cake Batter

05 - 1/2 cup unsalted butter, softened
06 - 1 cup granulated sugar
07 - 2 large eggs
08 - 1 teaspoon vanilla extract
09 - 1 1/2 cups all-purpose flour
10 - 1 1/2 teaspoons baking powder
11 - 1/2 teaspoon salt
12 - 1/2 cup whole milk

# How-To:

01 - Preheat the oven to 350°F and grease a 9-inch round cake pan.
02 - Melt 1/4 cup butter and pour it into the bottom of the pan, then evenly sprinkle 3/4 cup packed light brown sugar over the melted butter.
03 - Place pineapple rings over the sugar mixture and set a maraschino cherry in the center of each ring.
04 - In a mixing bowl, beat 1/2 cup softened unsalted butter and 1 cup granulated sugar until light and fluffy.
05 - Add eggs one at a time, beating well after each addition, then mix in 1 teaspoon vanilla extract.
06 - Whisk together 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt in a separate bowl.
07 - Add the flour mixture to the batter in three increments, alternating with 1/2 cup whole milk, beginning and ending with the flour mixture; stir just until combined.
08 - Pour the batter evenly over the pineapple rings in the pan and smooth the top. Bake for 40 minutes or until a toothpick inserted into the center comes out clean.
09 - Allow the cake to cool in the pan for 10 minutes before running a knife around the edges and inverting it onto a serving plate. Serve warm or at room temperature.

# Expert Advice:

01 -
  • The brown sugar melts into a deep caramel that tastes like luxury but requires no special skills.
  • The inversion moment creates genuine kitchen magic—that satisfying flip when the fruit pattern emerges perfectly.
  • It's forgiving enough for a first attempt but impressive enough to serve at dinner parties.
02 -
  • Don't skip letting the cake cool in the pan—invert too early and the caramel is still molten and will slide right off, too late and it hardens and sticks.
  • Use a metal cake pan, not glass or ceramic, because the metal heats evenly and gives you that perfect caramel without burning the edges.
  • The butter and sugar must be truly melted and mixed at the bottom of the pan before you arrange the fruit, or you'll have dry spots where the fruit sits directly on the pan.
03 -
  • Bring your eggs to room temperature before baking—they blend more completely into the batter, creating a more tender cake with better rise.
  • The key to a perfect inversion is that ten-minute cooling window; use your timer and don't eyeball it.
Go Back