Pineapple Upside-Down Cake (Printable Version)

Buttery vanilla cake with caramelized pineapple rings and cherries, served inverted for a beautiful presentation.

# What You'll 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 tsp vanilla extract
09 - 1 1/2 cups all-purpose flour
10 - 1 1/2 tsp baking powder
11 - 1/2 tsp salt
12 - 1/2 cup whole milk

# Directions:

01 - Preheat oven to 350°F. Generously grease a 9-inch round cake pan with butter or cooking spray.
02 - Melt 1/4 cup butter and pour into the prepared pan, spreading evenly across the bottom. Sprinkle brown sugar uniformly over the melted butter.
03 - Place pineapple rings over the brown sugar mixture in a single layer. Position 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 with an electric mixer until pale and fluffy, approximately 3 minutes.
05 - Add eggs one at a time, beating well after each addition. Mix in vanilla extract until fully incorporated.
06 - In a separate medium bowl, whisk together flour, baking powder, and salt until evenly blended.
07 - Add flour mixture to the butter mixture in three portions, alternating with milk in two additions. Begin and end with flour. Mix gently until just combined, being careful not to overmix.
08 - Carefully spoon the batter over the arranged pineapple rings, spreading evenly to cover completely without disturbing the fruit pattern.
09 - Bake for 38-42 minutes, or until a wooden toothpick inserted into the center comes out clean and the top is golden brown.
10 - Allow the cake to cool in the pan for 10 minutes. Run a thin knife around the edges to loosen, then place a serving plate over the pan and quickly invert to release the cake. Serve warm or at room temperature.

# Expert Tips:

01 -
  • The caramelized pineapple topping creates this incredible sticky sweet layer that seeps down into the cake while it bakes
  • It looks impressive but comes together with pantry staples you probably already have
02 -
  • Wait the full 10 minutes before flipping or the pineapple will stick to the pan instead of coming out beautifully
  • Do not let the cake cool completely in the pan or the caramel will harden and make inversion nearly impossible
03 -
  • Place your cake pan on a baking sheet to catch any caramel that bubbles over during baking
  • The cake is done when it pulls away slightly from the edges and springs back when touched
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