Pineapple Upside-Down Cake (Printable)

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

# 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 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

# How To Make:

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, coating the bottom evenly. Sprinkle brown sugar over the melted butter in an even layer.
03 - Place pineapple rings over the brown sugar mixture. Nestle 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, fluffy, and pale in color, approximately 3-4 minutes.
05 - Add eggs one at a time, beating well after each addition. Mix in vanilla extract until fully incorporated.
06 - In a separate bowl, whisk together flour, baking powder, and salt until evenly combined.
07 - Add the flour mixture to the butter mixture in three additions, alternating with the milk. Begin and end with the flour mixture, mixing only until just combined after each addition.
08 - Carefully spread the batter over the arranged pineapple rings, smoothing the top with an offset spatula or back of a spoon.
09 - Bake for 38-42 minutes, or until a wooden toothpick inserted into the center emerges clean and the top is golden brown.
10 - Allow the cake to rest in the pan for 10 minutes. Run a thin knife around the edges to loosen, then carefully invert onto a serving plate. Serve warm or at room temperature.

# Expert Advice:

01 -
  • The combination of caramelized brown sugar and sweet pineapple creates an incredible depth of flavor you just cannot get from regular cake
  • It looks impressive but comes together with basic pantry staples and zero fancy techniques
02 -
  • The 10-minute cooling period is crucial, flip too soon and the cake will break apart, wait too long and the caramel hardens
  • Pat your pineapple rings dry with paper towels before arranging them, otherwise you end up with soggy spots
03 -
  • Add a tablespoon of pineapple juice to the batter for extra pineapple flavor that permeates every bite
  • Room temperature ingredients are essential for proper aeration and even baking
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