Chocolate Stout Pineapple Upside-Down Cake Recipe
Malt undertones and caramelized fruit meld into a moist treat that shines the next day.

Category: Dessert — Cakes
Experience the fusion of classic comfort and bold flavors in this Chocolate Stout Pineapple Upside-Down Cake. By pairing tender, caramelized pineapple with the rich notes of cocoa and malty stout, this recipe transforms a beloved retro dessert into a memorable showstopper. Each bite delivers deep chocolate flavor, balanced by the sweet tang of pineapple and a hint of bitter stout, making it an impressive treat for any celebration or cozy night in.
Why This Recipe Works
- Caramelized Pineapple: Searing pineapple slices in butter and dark brown sugar creates a rich caramel topping that infuses the entire cake with intense flavor.
- Chocolate Stout Enhancement: The complex malty notes of stout beer amplify the chocolate’s depth, while the alcohol tenderizes the cake for a moist, soft crumb.
- Bold, Balanced Flavors: A generous dose of Dutch-processed cocoa powder and bittersweet chocolate keeps the chocolate flavor at the forefront, while the pineapple adds a refreshing tang and balance.
- Make-Ahead Friendly: This cake tastes even better the next day, as the flavors meld and the pineapple juices soak into the crumb, perfect for planning ahead for gatherings.
Ingredients
For the Topping | For the Cake |
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Optional for serving: Whipped cream or vanilla ice cream
Equipment
- 12-inch cast iron skillet or ovenproof stainless steel skillet (or a 10-inch cake pan for baking only)
- Mixing bowls
- Whisk
- Offset spatula or knife
- Cooling rack
Step-by-Step Instructions
1. Prepare the Pineapple Topping
- Preheat your oven to 350°F (175°C). Position a rack in the center of the oven.
- In your skillet, melt 4 tablespoons butter over medium heat. Add the brown sugar and whisk until the mixture is thick and bubbling, about 2 minutes.
- Arrange the pineapple slices in the sugar-butter mixture, covering the base and filling in gaps as desired. Cook for 5–7 minutes until the juices are just starting to turn golden and syrupy. Remove from heat and set aside while you prepare the cake batter.
2. Make the Chocolate Stout Cake Batter
- In a small saucepan over medium heat, bring the stout to a simmer. Remove from heat and add the chopped chocolate, whisking until smooth and glossy. Cool slightly.
- In a large bowl, cream together the 10 tablespoons butter and granulated sugar with a hand mixer or stand mixer until light and fluffy, about 3 minutes. Beat in the eggs one at a time, mixing well after each addition.
- In another bowl, whisk together the flour, cocoa, baking soda, and salt until well combined.
- Add the flour-cocoa mixture to the butter-egg mixture in three parts, alternating with the stout-chocolate mixture, beginning and ending with the dry ingredients. Mix on low until just combined. Do not overmix.
3. Assemble and Bake
- Carefully spoon the batter over the pineapple in the skillet, spreading it gently into an even layer with an offset spatula. Avoid disturbing the fruit arrangement beneath.
- Bake for 35–40 minutes, or until a toothpick inserted into the cake center comes out mostly clean. The cake should feel set in the center but moist.
4. Invert and Serve
- Let the cake cool in the skillet for 10–15 minutes (not longer, or the topping may stick). Run a knife around the edges to loosen.
- Set a large serving platter over the skillet and, using oven mitts, invert the cake onto the platter in one confident motion. If any pineapple sticks, replace it on top as needed.
- Let cool to room temperature. Slice and serve with whipped cream or ice cream if desired. The cake’s flavor deepens as it rests and is even better the next day.
Pro Tips and Troubleshooting
- Choosing Your Pineapple: Fresh, ripe pineapple yields the best texture and tang, but canned rings are a convenient and tasty alternative.
- Best Chocolate Stout: Use a robust, malty stout (like Guinness or a craft equivalent). Avoid overly bitter stouts as they can mask the chocolate and fruit.
- Prevent Sticking: If using a regular cake pan instead of a skillet, line the bottom with a parchment circle to guarantee easy release.
- Flavor Tweaks: Add a touch of ground ginger or cinnamon to the topping for a gentle spice that complements both chocolate and pineapple.
- Make-Ahead: The cake keeps well, wrapped airtight, for up to 2 days. Let it come to room temperature before serving for best texture.
Nutritional Information
Yield: | 10–12 servings |
Serving Size: | 1 slice (approximate) |
Calories per serving: | 510 kcal (estimate) |
Fat per serving: | 25g |
Carbohydrates: | 67g |
Protein: | 5g |
Note: Nutrition values are approximate and may vary with specific ingredients and portion sizes.
Variations
- Cherry Garnish: Add maraschino cherries to the center of each pineapple ring for a traditional look and a pop of color.
- Nuts: Sprinkle chopped toasted pecans or walnuts into the brown sugar topping for subtle crunch.
- Gluten-Free: Substitute your favorite gluten-free all-purpose flour blend for regular flour, following package weight guidelines.
- Alcohol-Free: Swap out the stout for brewed coffee or milk with a teaspoon of malted milk powder.
Serving Suggestions
- Pair with Whipped Cream: Dollops of lightly sweetened whipped cream or crème fraîche contrast deliciously with the rich cake.
- Ice Cream: Serve alongside vanilla or coconut ice cream for a tropical finish.
- Beverage Pairing: Complement with an espresso or more stout for a unified flavor experience.
Frequently Asked Questions (FAQs)
Q: Can I make this cake in advance?
A: Absolutely! The flavors enhance as the cake rests, and the pineapple juices further moisten the crumb. Store covered at room temperature for up to 2 days. For longer storage, refrigerate (bring to room temp before serving).
Q: Can I substitute the stout with another liquid?
A: Yes. Use brewed coffee, milk, or water for a non-alcoholic version, though the malty depth of stout is unique. Coffee enhances the chocolate flavor admirably.
Q: My cake stuck to the skillet! What did I do wrong?
A: Be sure to let the cake rest only 10–15 minutes before turning out—too hot and the cake may break, too cold and the topping can stick. Running a thin knife around the edges and using plenty of butter helps. If using a cake pan, consider a parchment circle.
Q: Can I use canned pineapple?
A: Certainly! Canned pineapple rings are convenient and work beautifully. Drain well and pat dry with paper towels for best results. Arrange as desired in the topping.
Q: How do I store leftovers?
A: Store slices in an airtight container at room temperature for up to 2 days or refrigerate for up to 4 days. The cake remains moist and flavorful even after a couple of days due to the syrupy topping.
Conclusion
This Chocolate Stout Pineapple Upside-Down Cake isn’t just a treat for chocolate lovers—it’s a special-occasion-worthy dessert that bridges the gap between nostalgia and bold, grown-up flavors. By caramelizing pineapple in butter and brown sugar, infusing the cake with stout and chocolate, and baking it all together, you create a moist, unforgettable cake that’s just as impressive to look at as it is to eat. Enjoy this treat at your next celebration, holiday dinner, or whenever you crave the comfort of a classic with a decadent twist.
References
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