Pineapple Upside-Down Cake (Printable)

Classic buttery vanilla cake with caramelized pineapple rings and cherries, baked golden and served inverted.

# What You'll Need:

→ Caramelized 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:

01 - Preheat oven to 350°F. Grease a 9-inch round cake pan thoroughly with butter or cooking spray.
02 - Melt 1/4 cup butter and pour into the bottom of the prepared pan. Sprinkle brown sugar evenly over the melted butter to form a caramel layer.
03 - Arrange pineapple rings over the brown sugar mixture in a decorative pattern. Place a maraschino cherry in the center of each pineapple ring.
04 - In a large mixing bowl, beat 1/2 cup softened butter and granulated sugar together until light and fluffy, approximately 3 minutes.
05 - Add eggs one at a time, beating well after each addition. Stir in vanilla extract until fully incorporated.
06 - In a separate bowl, whisk together flour, baking powder, and salt until evenly distributed.
07 - Add flour mixture to the butter mixture in three additions, alternating with milk and beginning and ending with flour. Mix gently until just combined, being careful not to overmix.
08 - Spoon the batter evenly over the pineapple and cherry arrangement. Smooth the top with a spatula to create an even surface.
09 - Bake for 38-42 minutes, or until the top is golden brown and a toothpick inserted into the center comes out clean.
10 - Let the cake cool in the pan for 10 minutes. Run a knife around the edges to loosen, then invert onto a serving plate. Serve warm or at room temperature.

# Expert Tips:

01 -
  • The contrast between the tender vanilla cake and sticky sweet topping is pure comfort
  • It looks impressive but comes together with ingredients you probably have right now
  • The moment you flip that pan feels like a tiny celebration every single time
02 -
  • Wait exactly 10 minutes before flipping, or the fruit will stick, but don't wait longer or the caramel will harden
  • That sizzling sound when the brown sugar hits the butter means you're doing something very right
  • Invert quickly and confidently, hesitation is your enemy in that crucial moment
03 -
  • Add a tablespoon of pineapple juice to the batter for extra pineapple flavor without affecting the texture
  • Room temperature ingredients prevent the batter from separating and give you a more tender crumb
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