Pineapple Upside-Down Cake (Printable Version)

Buttery vanilla cake with caramelized pineapple rings and maraschino cherries, baked golden and inverted for beautiful 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. Grease a 9-inch round cake pan thoroughly with butter or cooking spray.
02 - Melt 1/4 cup butter and pour evenly into the prepared pan. Sprinkle brown sugar across the melted butter, spreading into a uniform layer.
03 - Place pineapple rings over the brown sugar mixture in a single, even layer. Center one maraschino cherry inside each pineapple ring.
04 - In a large mixing bowl, beat softened butter and granulated sugar together 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 dry ingredients to butter mixture in three portions, alternating with milk in two additions. Begin and end with flour mixture, mixing only until just combined after each addition.
08 - Spoon batter carefully over pineapple arrangement, spreading evenly with an offset spatula to avoid disturbing the topping pattern.
09 - Bake for 38-42 minutes until golden brown and a toothpick inserted into the center emerges clean or with moist crumbs only.
10 - Cool in pan for 10 minutes. Run a thin knife around the edges, then invert onto a serving plate. Serve warm or at room temperature.

# Expert Tips:

01 -
  • The combination of buttery vanilla cake and sticky caramel topping creates the perfect balance of sweet and tender
  • Its a stunning dessert that looks impressive but comes together with simple pantry ingredients
  • This retro classic brings nostalgia to the table while feeling completely timeless
02 -
  • Waiting exactly 10 minutes before flipping is crucial, too soon and the cake falls apart, too late and the caramel hardens to the pan
  • Arrange your pineapple rings thoughtfully since this pattern will be the top of your finished cake
  • The cake is done when the edges pull away slightly from the pan and a tester comes out clean
03 -
  • Use a light colored pan to prevent the caramel from burning on the bottom
  • If any pineapple sticks to the pan after flipping, simply arrange it back on the cake while still warm
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