Pineapple Upside-Down Delight (Printable)

Buttery vanilla cake with caramelized pineapple rings and cherries, baked to golden perfection and served inverted.

# What You Need:

→ Topping

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

# Directions:

01 - Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan.
02 - Melt 1/4 cup butter and pour into the bottom of the pan. Sprinkle 3/4 cup brown sugar evenly over the melted butter.
03 - Arrange pineapple rings over the sugar mixture. Place one maraschino cherry in the center of each pineapple ring.
04 - In a mixing bowl, cream 1/2 cup softened butter and 1 cup granulated sugar until light and fluffy.
05 - Beat in eggs one at a time, then add 1 teaspoon vanilla extract and mix well.
06 - In a separate bowl, whisk together 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt.
07 - Add the flour mixture to the creamed batter in three additions, alternating with 1/2 cup milk, starting and ending with flour. Stir until just combined.
08 - Spoon the batter evenly over the pineapple rings and smooth the surface.
09 - Bake for 38 to 42 minutes, or until a toothpick inserted into the center comes out clean.
10 - Allow the cake to cool in the pan for 10 minutes. Run a knife around the edges, then invert onto a serving plate. Serve warm or at room temperature.

# Expert Advice:

01 -
  • It looks restaurant-worthy but comes together in under an hour, which means you can be a hero at dinner with minimal stress.
  • The caramelized pineapple creates its own sauce—no frosting needed, just pure buttery-sweet elegance on every plate.
02 -
  • That 10-minute cooling window is non-negotiable; flip too early and the cake falls apart, too late and the caramel sets and sticks to the pan instead of the cake.
  • If the fruit shifts when you're pouring the batter, gently push pieces back into place—they move more than you'd think, but they can be rearranged before the oven seals everything in place.
03 -
  • Use room-temperature eggs and softened butter—cold ingredients won't cream properly and your cake will be denser than it should be.
  • Line the bottom of your cake pan with parchment paper before adding the butter and sugar; it's an extra layer of insurance that the flip will work perfectly.
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