Rum-Glazed Pineapple Upside-Down Cake

By AislePrompt Test Kitchen · Reviewed by AislePrompt Editorial · ·

A moist, buttery cake topped with caramelized pineapple rings glazed with a rich rum-infused brown sugar sauce. This caribbean-inspired caribbean ready in about 60 minutes pairs (1 stick) softened unsalted butter, packed brown sugar, rings, fresh or canned pineapple rings 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.

★ 4.3 (9 ratings) Prep: 15 min Cook: 45 min Serves 8 Caribbean cuisine 350 cal/serving
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Ingredients

Instructions

  1. Step 1: Preheat your oven to 350°F (175°C). In a 9-inch round cake pan, melt 1/4 cup unsalted butter over low heat. Stir in 3/4 cup packed brown sugar and 3 tbsp light rum until combined and bubbly. Arrange 6 pineapple rings evenly over the mixture, placing a maraschino cherry in the center of each ring if using. Set aside.
  2. Step 2: In a medium bowl, whisk together 1 1/2 cups all-purpose flour, 1 cup granulated sugar, 1 1/2 tsp baking powder, and 1/2 tsp salt.
  3. Step 3: In another bowl, beat 1 large egg with 1/2 cup whole milk and 1 tsp vanilla extract. Slowly add the wet ingredients to the dry and mix until smooth.
  4. Step 4: Pour the batter evenly over the pineapple layer in the pan. Bake for 40-45 minutes until a toothpick inserted in the center comes out clean and the cake is golden brown around the edges.
  5. Step 5: Let the cake cool for 10 minutes, then run a knife around the edges and invert onto a serving plate to reveal the caramelized pineapple topping.

Frequently asked questions

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

Total time is about 60 minutes (15 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-Glazed 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 packed brown sugar from drying out.

Can I substitute ingredients in Rum-Glazed 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-Glazed 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-Glazed 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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