Classic Pineapple Upside-Down (Printable version)

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

# What You'll 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

# How to Make:

01 - Preheat oven to 350°F. Grease a 9-inch round cake pan.
02 - Melt 1/4 cup butter and pour into the bottom of the pan. Evenly sprinkle 3/4 cup brown sugar over melted butter.
03 - Place pineapple rings over the sugar mixture, then place a maraschino cherry in the center of each 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, followed by the vanilla extract.
06 - In a separate bowl, whisk together flour, baking powder, and salt.
07 - Alternately add the flour mixture and 1/2 cup milk into the creamed mixture in three additions, beginning and ending with flour. Mix until just combined.
08 - Spoon batter evenly over pineapple rings and smooth the surface.
09 - Bake for 40 minutes, or until a toothpick inserted into the center comes out clean.
10 - Allow cake to cool in the pan for 10 minutes. Run a knife around edges and invert onto a serving plate. Serve warm or at room temperature.

# Expert Advice:

01 -
  • The caramelized pineapple topping becomes glossy and sticky-sweet, nothing like the fruit inside the tin.
  • It looks impressive enough to serve at a dinner party but easy enough that you won't stress the whole time it's baking.
  • The vanilla cake stays incredibly moist underneath, soaking up those brown sugar and butter juices.
02 -
  • If you skip the 10-minute cooling window, the caramel is still liquid and slides off; too long and it hardens and cracks when you flip it.
  • Don't drain the pineapple directly into the sink—reserve a tablespoon or two to brush on the cake for extra moisture and tropical flavor.
03 -
  • If the pineapple rings are large, halve them so they fit snugly in the pan without overlapping too much, giving the caramel room to work.
  • Make sure your cake pan is absolutely level in the oven, or the caramel will pool to one side and create an uneven topping.
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