Pineapple Upside-Down Cake (1960s Classic) | CookOS

Pineapple Upside

Name: Pineapple Upside-Down Cake (1960s Classic)
Prep time: 20 min
Cook time: 45 min
Total time: 1 h 5 min
Yield: 10 servings
Cuisine: American
Ingredients: 1/2 cup unsalted butter, melted; 1 cup packed brown sugar; 1 (20 oz) can pineapple slices; 1 jar maraschino cherries; 2 cups all-purpose flour; 1 cup granulated sugar; 3 large eggs; 1 cup milk; 1/2 cup unsalted butter, softened; 2 tsp baking powder; 1/2 tsp salt

This pineapple upside-down cake features a caramelized brown sugar and butter base topped with pineapple rings and maraschino cherries, crowned with a tender vanilla sponge cake that inverts perfectly for a show-stopping presentation.

🌍American 🏷️Pineapple upside-down cake 🏷️Cake 🏷️Dessert 🏷️Baking Classic

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Total

1h 5m

Servings

Difficulty

Medium

Est. Cost

$22–$36

Recipe Source

View original recipe

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Ingredients

1/2 cup unsalted butter, melted
1 cup packed brown sugar
1 (20 oz) can pineapple slices
1 jar maraschino cherries
2 cups all-purpose flour
1 cup granulated sugar
3 large eggs
1 cup milk
1/2 cup unsalted butter, softened
2 tsp baking powder
1/2 tsp salt

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Instructions

1
Prepare the topping by combining melted butter and brown sugar in the bottom of a bundt pan.
2
Arrange pineapple slices and maraschino cherries over the brown sugar mixture in the pan.
3
In a large bowl, cream together softened butter and granulated sugar. Beat in eggs one at a time.
4
In a separate bowl, whisk together flour, baking powder, and salt. Sift the dry ingredients into the wet ingredients, alternating with milk, and mix until just combined.
5
Pour the batter evenly over the fruit in the bundt pan.
6
Bake until a wooden skewer inserted into the center comes out clean. Let cool in the pan for a few minutes before inverting onto a serving plate.

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Tips & Notes

Pro tips

Drain canned pineapple thoroughly and pat slices dry to prevent a soggy caramel layer.
Arrange pineapple rings and cherries while the butter-brown sugar base is still warm but set, about 2–3 minutes after pouring.
Invert the cake while still warm (5 minutes post-bake) so the caramel adheres properly; waiting too long causes the topping to harden and may stick to the pan.
Use softened butter for the cake batter to ensure even mixing and a tender crumb.

Substitutions

All-purpose flour → cake flour (use same amount; cake flour yields a more delicate crumb)
Maraschino cherries → candied cherries or dried cranberries (for less sweetness or color variation)
Milk → buttermilk (adds tang and ensures a slightly tender cake)
Unsalted butter → salted butter (reduce added salt elsewhere or omit)

Storage & make-ahead

Store in the pan, covered, at room temperature for up to 2 days. Serve at room temperature or gently reheat covered in a 300°F oven for 10 minutes.

Equipment

9-inch round cake pan · stand mixer or hand mixer

Common Questions

Can I use fresh pineapple instead of canned?

Fresh pineapple works but may release excess moisture; drain canned pineapple thoroughly and pat slices dry before arranging. Canned is more reliable for consistent results.

What's the best way to invert the cake without breaking it?

Cool the cake for 5 minutes after baking (still warm), then run a thin knife around the edges, place a serving plate on top, and invert in one confident motion. Let it sit for 30 seconds before lifting the pan.

Can I make this cake ahead of time?

Bake up to 2 days ahead and store covered at room temperature. Keep the cake in the pan until serving to preserve the caramelized topping.

Why is my caramel layer too hard or sticky?

Hard: overcooking; sticky: undercooking or excess pineapple juice. Bake until a toothpick inserted in the cake (not the topping) comes out clean, and ensure pineapple is well-drained.