Chocolate-Stout Upside-Down Pineapple Cake Recipe

Tipsy cake. María del Mar Sacasa

A boozy, rich, chocolate stout-flavored pineapple upside-down cake.

Recipe Facts

Active: 30 mins
Total: 2 hrs 30 mins
Serves: 12 servings

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  • For the Pineapple Layer:
  • 1 stick (4 ounces) unsalted butter, melted
  • 1 cup (about 7 ounces) packed dark brown sugar
  • 1 large pineapple, peeled and cored or 1 pound fresh pineapple spears
  • For the Chocolate-Stout Cake:
  • 2 cups chocolate stout or regular stout
  • 2 sticks (8 ounces) unsalted butter
  • 1/3 cup natural cocoa powder
  • 2 cups (about 10 ounces) all-purpose flour
  • 2 cups (about 14 ounces) packed dark brown sugar
  • 1 teaspoon baking powder
  • 1 teaspoon salt
  • 1 teaspoon baking soda
  • 1/2 cup buttermilk, at room temperature
  • 3 large eggs, at room temperature, lightly beaten
  • 2 teaspoons pure vanilla extract


  1. For the Pineapple Layer: Adjust oven rack to middle position and preheat oven to 350°F. Trim pineapple into 18 spears, 4- by 1/2-inches. If using fresh pineapple spears, trim them to approximately that size.

  2. Pour melted butter into a 13- by 9-inch baking pan tilting to distribute evenly. With pastry brush, grease sides of pan with some of the butter. Sprinkle butter evenly with brown sugar, then, arrange pineapple spears in 2 parallel rows.

  3. For the Chocolate-Stout Cake: Bring stout to boil in small saucepan over medium-high heat, stirring occasionally to prevent bubbling over. Cook until reduced to 1 cup, 10 to 12 minutes. Reduce heat to medium and stir in butter and cocoa powder. Cook, stirring, until mixture is homogenous.

  4. Whisk flour, brown sugar, baking powder, and salt together in large bowl. Whisk stout mixture into flour mixture.

  5. Stir baking soda into buttermilk until completely dissolved and whisk into batter. Whisk in eggs and vanilla. Scrape batter into prepared pan, spreading evenly over pineapple. Bake until tester inserted in center of cake comes out clean, about 35 to 45 minutes.

  6. Transfer cake to cooling rack and cool 10 minutes, then, invert directly onto rack and cool to room temperature, about 1 hour. Serve.

Special equipment

13- by 9-inch baking pan, pastry brush, small saucepan, whisk, cooling rack

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