Pineapple Upside-Down Cake (Printable)

Buttery vanilla cake crowned with caramelized pineapple and cherries, baked golden and inverted for serving.

# What You Need:

→ Topping

01 - 1/4 cup unsalted butter
02 - 3/4 cup light brown sugar, packed
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

# How to Make It:

01 - Preheat oven to 350°F. Grease a 9-inch round cake pan.
02 - Melt 1/4 cup butter and evenly pour into the bottom of the pan. Sprinkle 3/4 cup light brown sugar over the melted butter.
03 - Place pineapple rings over the sugar mixture and center a maraschino cherry inside each ring.
04 - In a mixing bowl, beat 1/2 cup softened butter with 1 cup granulated sugar until light and fluffy.
05 - Beat in eggs one at a time, then blend 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.
07 - Add the flour mixture to the butter mixture in three parts, alternating with 1/2 cup whole milk, starting and ending with flour. Mix gently until just combined.
08 - Spoon batter evenly over the arranged pineapple and cherries, smoothing the surface.
09 - Bake for 38 to 42 minutes or until a toothpick inserted in the center comes out clean.
10 - Allow to cool in the pan for 10 minutes. Run a knife around the edges and invert onto a serving plate. Serve warm or at room temperature.

# Expert Suggestions:

01 -
  • The caramelized sugar and butter create a glossy, sticky-sweet topping that feels indulgent without being heavy.
  • It's foolproof enough for beginners but impressive enough to serve at a dinner party without anyone knowing how simple it really was.
  • Warm from the oven with a scoop of vanilla ice cream, this cake tastes like comfort with a tropical twist.
02 -
  • The 10-minute cooling window is non-negotiable; flip too early and the cake might fall apart, too late and the caramel hardens and won't cling to the cake anymore.
  • If a piece of pineapple sticks to the pan, carefully lift it off and press it back into place on the cake—no one will ever notice this tiny fix.
03 -
  • If your pan doesn't have a removable bottom, line it with parchment paper for extra insurance against sticking.
  • Use an oven thermometer to make sure your oven is actually at the temperature it claims—this is the difference between perfect and overdone.
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