Buttery pineapple upside-down (Printable)

Golden vanilla cake crowned with caramelized pineapple rings and cherries, baked to moist perfection.

# What You'll Need:

→ Topping

01 - 1/4 cup unsalted butter
02 - 3/4 cup packed light brown sugar
03 - 8 to 10 canned pineapple rings, drained
04 - 8 to 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 oven to 350°F. Grease a 9-inch round cake pan.
02 - Melt 1/4 cup butter and pour into the bottom of the pan. Evenly sprinkle 3/4 cup brown sugar over the melted butter.
03 - Place pineapple rings over the sugar mixture, then position one maraschino cherry in the center of each ring.
04 - In a mixing bowl, beat 1/2 cup softened butter and 1 cup granulated sugar until light and fluffy.
05 - Add eggs one at a time to the creamed mixture, followed by 1 teaspoon vanilla extract; beat well after each addition.
06 - Whisk together 1 1/2 cups flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt in a separate bowl.
07 - Alternately add the flour mixture and 1/2 cup milk to the batter in three additions, starting and ending with flour; mix until just combined.
08 - Pour batter evenly over the pineapple rings and smooth the surface.
09 - Bake for 38 to 42 minutes until a toothpick inserted in the center comes out clean.
10 - Allow cake to cool in the pan for 10 minutes; run a knife around the edges and invert onto a serving plate. Serve warm or at room temperature.

# Expert Advice:

01 -
  • The caramelized pineapple topping creates a restaurant-quality presentation that guests always mistake for something far more difficult than it actually is.
  • Buttery, tender crumb pairs perfectly with that sweet, tangy fruit layer so you get complexity without fuss.
  • The whole thing comes together in under two hours from start to finish, making it ideal for last-minute dessert emergencies.
02 -
  • That 10-minute cooling window is non-negotiable; invert too early and the cake falls apart, too late and the caramel hardens and won't release cleanly.
  • If pineapple juice gets into your batter, the acid can throw off your rise, so drain those rings truly well.
  • Room temperature ingredients mix more smoothly and create better texture than cold ones straight from the fridge.
03 -
  • If the caramel sticks to the bottom of the pan after inversion, quickly return the cake to the oven for 2–3 minutes to warm and loosen it, then plate it again.
  • Substitute fresh pineapple if canned isn't available, but blanch the rings first to prevent the baking powder from reacting with the natural enzymes and making your cake gummy.
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