Rum-Soaked Pineapple Upside-Down Cake

By AislePrompt Test Kitchen · Reviewed by AislePrompt Editorial · ·

A moist, buttery cake topped with caramelized pineapple rings soaked in dark rum, creating a tropical dessert with a rich depth of flavor. This caribbean-inspired caribbean ready in about 65 minutes pairs (1 stick) unsalted butter, softened, divided brown sugar, rings pineapple rings, canned or fresh for a weeknight-friendly dinner that comes together with one pan and minimal cleanup. Each serving lands at about 350 calories and feeds 8, so it slots cleanly into a weekly meal plan and pairs well with a quick salad or grain on the side. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart.

★ 4.1 (15 ratings) Prep: 20 min Cook: 45 min Serves 8 Caribbean cuisine 350 cal/serving
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Ingredients

Instructions

  1. Step 1: Preheat oven to 350°F. In a 9-inch round cake pan, melt 1/4 cup unsalted butter over low heat. Stir in 1/2 cup brown sugar until combined and bubbling. Arrange 6 pineapple rings evenly over the sugar mixture, then pour 1/4 cup dark rum evenly over the pineapples.
  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 1/2 cup softened unsalted butter with 3/4 cup granulated sugar until light and fluffy, about 3 minutes. Add 2 large eggs one at a time, beating well after each addition, then mix in 1 tsp vanilla extract.
  4. Step 4: Alternate adding flour mixture and 1/2 cup whole milk to the butter mixture, beginning and ending with flour. Mix just until combined and batter is smooth.
  5. Step 5: Pour batter over the pineapple and rum layer in the pan, smoothing the top with a spatula. Bake for 40-45 minutes until a toothpick inserted in the center comes out clean.
  6. Step 6: Let cake cool in the pan for 10 minutes, then carefully invert onto a serving plate so the pineapple side is up. Serve warm or at room temperature.

Frequently asked questions

How long does Rum-Soaked Pineapple Upside-Down Cake take to make?

Total time is about 65 minutes (20 min prep + 45 min cook). Most home cooks find this fits comfortably into a weeknight; double the batch on Sunday for two dinners.

How do I store leftover Rum-Soaked Pineapple Upside-Down Cake?

Cool to room temperature within 2 hours, then store in an airtight container in the fridge for up to 4 days. Reheat covered in a 350°F oven for 10-12 minutes, or microwave at 70% power in 60-second bursts to keep divided brown sugar from drying out.

Can I substitute ingredients in Rum-Soaked Pineapple Upside-Down Cake?

Yes — most ingredients in this recipe have flexible swaps. For oil, use any neutral high-smoke-point oil (avocado, grapeseed, refined coconut). For aromatics, dried herbs at ⅓ the volume of fresh work in a pinch. The full ingredient list is shoppable on Instacart so you can see substitutes in real time.

How do I scale Rum-Soaked Pineapple Upside-Down Cake for a different number of people?

The recipe is written for 8 servings. Multiply each ingredient by (your serving target / 8). Cook time stays roughly the same up to 2x; for 3-4x batches, switch from a skillet to a sheet pan or stockpot so the food isn't crowded — overcrowding steams instead of browns.

What goes well with Rum-Soaked Pineapple Upside-Down Cake?

Caribbean caribbean like this pair well with a simple grain (rice, couscous, or crusty bread), a quick salad with acid (lemon vinaigrette, pickled onions), and a pan sauce or yogurt-based dip. Tap "Plan a meal with the AI" to get specific side suggestions.

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