Caramelized Pineapple Upside-Down Cake

By AislePrompt Editorial · Published 2026-06-13 · Updated 2026-06-13

Moist yellow cake topped with caramelized fresh pineapple rings and brown sugar glaze, baked upside-down for a glossy, tropical finish. This American-inspired recipe, ready in about 60 minutes, layers fresh pineapple rings, unsalted butter, packed brown sugar into a dessert worth slowing down for — great for weekend baking, holiday tables, or any time you want a sweet payoff at the end of a meal. Each serving lands at about 360 calories and feeds 8, so it slots into a weekend bake or a special-occasion dessert tray. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart. Nutrition values are approximate, calculated from USDA FoodData Central (fdc.nal.usda.gov) — verify against ingredient labels for any health-driven dietary plan.

Ingredients

• 6 rings, about 1/2 inch thick fresh pineapple rings
• 6 tbsp, divided unsalted butter
• 3/4 cup packed brown sugar
• 1 1/2 cups all-purpose flour
• 1 cup granulated sugar
• 1 1/2 tsp baking powder
• 1/4 tsp salt
• 2 large eggs
• 1/2 cup whole milk
• 2 tsp pure vanilla extract

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Instructions

1. Step 1: Preheat oven to 350°F. In a 9-inch round cake pan, melt 4 tbsp unsalted butter over low heat, then sprinkle 3/4 cup packed brown sugar evenly over the melted butter; arrange 6 fresh pineapple rings on top in a single layer.
2. Step 2: In a medium bowl, whisk together 1 1/2 cups all-purpose flour, 1 1/2 tsp baking powder, and 1/4 tsp salt.
3. Step 3: In a large bowl, beat 1 cup granulated sugar with 2 tbsp softened unsalted butter until light and fluffy.
4. Step 4: Add 2 large eggs one at a time, beating well after each addition, then stir in 2 tsp pure vanilla extract.
5. Step 5: Alternately add the flour mixture and 1/2 cup whole milk to the butter mixture, beginning and ending with flour, mixing until just combined.
6. Step 6: Pour the batter evenly over the pineapple and brown sugar layer in the pan.
7. Step 7: Bake for 40-45 minutes until a toothpick inserted into the center comes out clean and the cake edges pull away slightly from the pan.
8. Step 8: Let the cake cool in the pan for 10 minutes, then carefully invert onto a serving plate; gently lift the pan away to reveal the caramelized pineapple topping.
9. Step 9: Serve warm or at room temperature, optionally with whipped cream or vanilla ice cream.