Pineapple Upside-Down Cake (Printable)

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

# Ingredient List:

→ 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:

01 - Preheat your 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 bottom of the prepared pan. Sprinkle brown sugar evenly over the melted butter, spreading to create an even layer.
03 - Place pineapple rings over the 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 together until light and fluffy, 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 well blended.
07 - Add the flour mixture to the butter mixture in three portions, alternating with the milk. Begin and end with the flour mixture. Mix only until just combined to avoid overworking the batter.
08 - Carefully spoon the batter over the arranged pineapple and cherries. Smooth the top with an offset spatula to ensure even distribution.
09 - Bake for 38-42 minutes, or until a wooden toothpick inserted into the center comes out clean. The top should be golden brown and spring back when lightly touched.
10 - Allow the cake to cool in the pan for 10 minutes. Run a knife around the edges to loosen, then immediately invert onto a serving plate. Serve warm or at room temperature.

# Expert Hints:

01 -
  • The butterscotch-like topping forms itself in the oven, no candy thermometer required
  • This vintage dessert somehow feels retro and timeless all at once
  • It travels beautifully to potlucks and always steals the show
02 -
  • Waiting the full 10 minutes before flipping is crucial, too soon and the fruit slides, too late and it sticks
  • The sizzling sound you hear when pouring the batter over the hot sugar butter is exactly right
  • If any pineapple sticks to the pan, simply rearrange it on the cake while still warm
03 -
  • Use a light-colored cake pan to prevent the edges from overbaking before the center is done
  • Place a baking sheet on the rack below to catch any potential sugar drips
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