Preheat your oven to 350°F (175°C). Generously grease your muffin pan or line with parchment-style cupcake liners (note: traditional paper liners may stick due to caramelization).
Step 2: Make the Caramel Topping
In a small bowl, mix the melted butter and brown sugar until smooth.
-
Spoon about 1 tablespoon of the mixture into the bottom of each muffin cup.
-
Place a pineapple ring, half-ring, or chunk over the sugar mixture.
-
Add a cherry in the center if using.
This layer will become the glossy top once the cupcakes are inverted.
Step 3: Prepare the Dry Ingredients
In a medium bowl, whisk together:
-
Flour
-
Baking powder
-
Salt
Set aside.
Step 4: Cream the Butter and Sugar
In a large bowl, beat the softened butter and granulated sugar until light and fluffy (about 2–3 minutes). This step is crucial for a tender crumb.
Step 5: Add Eggs and Vanilla
Add eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
Step 6: Combine Wet and Dry Ingredients
Add the dry ingredients in three additions, alternating with the pineapple juice and milk. Begin and end with dry ingredients. Mix just until combined—do not overmix.
Step 7: Assemble the Cupcakes
Spoon the batter over the pineapple topping, filling each cup about ¾ full.
Step 8: Bake
Bake for 20–25 minutes, or until a toothpick inserted into the center comes out clean.
Step 9: Cool and Flip
Let the cupcakes cool in the pan for 5–7 minutes only.
Place a tray or baking sheet over the pan and carefully invert. Lift the pan gently to reveal the caramelized pineapple tops.
Tip: Don’t wait too long to flip—caramel can harden and stick.
Texture and Flavor Notes
-
Top: Sticky, buttery, caramelized pineapple
-
Center: Soft, moist vanilla crumb
-
Finish: Light tropical tang balanced with rich sweetness
These cupcakes strike the perfect balance between indulgent and refreshing.
Expert Baking Tips
-
Drain pineapple thoroughly to avoid soggy cupcakes
-
Use room-temperature ingredients for even mixing
-
Don’t overbake—pineapple juice keeps them moist, but dryness can occur if overdone
-
If any pineapple sticks, gently replace it while still warm
Variations You’ll Love
Coconut Pineapple Upside-Down Cupcakes
Add ¼ cup shredded coconut to the batter and replace milk with coconut milk.
Spiced Pineapple Cupcakes
Add ½ teaspoon cinnamon and a pinch of nutmeg for a warm twist.
Rum Pineapple Version
Replace 2 tablespoons of pineapple juice with dark rum (adults only).
Mini Upside-Down Cupcakes
Use a mini muffin pan and bake for 12–15 minutes—perfect for dessert platters.
Serving Suggestions
-
Serve slightly warm with whipped cream
-
Pair with vanilla ice cream for a plated dessert
-
Dust lightly with powdered sugar for elegance
-
Garnish with toasted coconut or mint leaves
Storage and Make-Ahead Tips
-
Room temperature: Up to 24 hours, covered
-
Refrigerator: Up to 4 days in an airtight container
-
Freezer: Freeze without toppings for up to 2 months
To reheat, microwave for 10–15 seconds for a fresh-baked feel.
Nutritional Overview (Approximate per cupcake)
-
Calories: 280
-
Fat: 14g
-
Carbohydrates: 36g
-
Sugar: 24g
-
Protein: 3g
Frequently Asked Questions
Can I use fresh pineapple?
Yes! Just slice thinly and pat dry.
Do I need cupcake liners?
Optional, but greasing the pan works best for clean release.
Can I make this gluten-free?
Yes—use a 1:1 gluten-free baking flour blend.
Why This Recipe Works
This recipe balances classic technique with modern convenience. The brown sugar–butter caramel melts into the pineapple, while the pineapple juice enriches the cake batter, ensuring moisture without heaviness. The result is a cupcake that tastes nostalgic yet looks bakery-perfect.
Final Thoughts
These Pineapple Upside-Down Cupcakes are proof that classic desserts never go out of style—they just evolve. Moist, golden, and crowned with caramelized fruit, they’re perfect for birthdays, holidays, potlucks, or anytime you crave a tropical escape.
Bake them once, and they’ll earn a permanent spot in your dessert rotation. 🍍🧁
