How to Bake Perfect Pineapple Upside-Down Cupcakes in 6 Steps

If you’re craving a sweet treat that’s both nostalgic and stunning to serve, look no further than Pineapple Upside-Down Cupcakes. With their golden caramelized topping, juicy pineapple rings, and rich, fluffy base, these mini delights capture everything we love about the classic cake in a personal-sized portion.

Originating in the early 20th century, pineapple upside-down cakes became a sensation with the introduction of canned pineapple, making this dessert an American staple. Today, cupcakes bring a modern twist to the tradition, perfect for parties, holidays, or just satisfying a weeknight craving.

Not only are these cupcakes quick to make, but they’re also budget-friendly and adaptable to various dietary needs. Plus, they make a beautiful presentation with minimal effort.

Ready to master these bite-sized beauties? Let’s dive into the step-by-step recipe for baking the perfect Pineapple Upside-Down Cupcakes.

Ingredients

For the Topping:

• 1/4 cup (1/2 stick) unsalted butter, melted
• 1/2 cup packed light brown sugar
• 6 canned pineapple rings (in juice, not syrup), sliced in halves or quarters
• 12 maraschino cherries

For the Cupcake Batter:

• 1 1/2 cups all-purpose flour
• 1/2 cup granulated sugar
• 1/4 cup packed light brown sugar
• 1/2 tsp baking powder
• 1/4 tsp baking soda
• 1/4 tsp salt
• 1/2 cup unsalted butter, softened
• 2 large eggs
• 1/3 cup sour cream (or plain Greek yogurt)
• 1/2 cup pineapple juice (reserved from can)
• 1 tsp vanilla extract

Substitutions:

• Gluten-free flour blend for a GF version
• Coconut oil instead of butter for a dairy-free option
• Applesauce for eggs (1/4 cup per egg) for a vegan alternative

Note: Opt for high-quality canned pineapple with no added sugar for the best flavor.

Equipment/Tools Needed

• 12-cup muffin tin
• Cupcake liners (optional)
• Mixing bowls (2-3)
• Electric mixer or whisk
• Spatula
• Cooling rack
• Measuring cups and spoons

Alternatives: If you don’t have a muffin tin, use silicone cupcake molds placed on a baking sheet.

Step-by-Step Instructions

Step 1: Preheat and Prepare

Preheat your oven to 350°F (175°C). Lightly grease a 12-cup muffin tin or line with cupcake liners.

Step 2: Create the Topping

Pour melted butter evenly into each muffin cup. Add 2 teaspoons of brown sugar to each cup and mix slightly. Place a halved or quartered pineapple slice and a maraschino cherry in each.

Step 3: Mix the Dry Ingredients

In a medium-sized bowl, combine the flour, baking powder, baking soda, and salt, then whisk until well mixed. Set aside.

Step 4: Beat the Wet Ingredients

In a large bowl, beat the butter with the granulated and brown sugars until the mixture is light and fluffy. Add the eggs one at a time, mixing well after each addition. Stir in the sour cream, vanilla extract, and pineapple juice until fully combined.

Step 5: Combine and Mix

Gradually add the dry ingredients to the wet mixture. Mix until just combined; do not overmix. The batter should be thick but pourable.

Step 6: Fill and Bake

Spoon the batter evenly over the pineapple in each muffin cup, filling each about three-quarters full. Bake for 20–25 minutes, or until a toothpick inserted into the center comes out clean.

Step 7: Cool and Invert

Let cupcakes cool in the tin for 5 minutes. Run a knife around the edges, then carefully invert onto a wire rack or tray. Serve warm or at room temperature.

Expert Tips & Variations

• Don’t overfill the cups: Leave room for the batter to rise.
• Use silicone pans: Easier removal and less risk of sticking.
• Room temp ingredients: Ensure even mixing and better texture.
• Try a pineapple cake mix: For an even quicker recipe!
• Mini versions: Use mini muffin pans for bite-sized treats.
• Switch fruits: Use peach slices or mango for a tropical twist.
• Spice it up: Add a pinch of cinnamon or nutmeg to the batter.

Avoid overbaking as it can dry out the cupcakes. Watch for golden tops and a springy texture.

Nutritional Information (Per Cupcake)

• Calories: 210
• Protein: 2g
• Carbohydrates: 28g
• Sugars: 18g
• Fat: 10g
• Saturated Fat: 6g
• Fiber: 1g

Health benefits: Pineapple is rich in vitamin C and antioxidants, and using pineapple juice adds flavor without excess sugar.

Disclaimer: Nutritional values are estimates and may vary by brand and portion.

Storage & Reheating Instructions

• Refrigerate in an airtight container for up to 4 days.
• Freeze individually wrapped in foil or containers for up to 2 months.
• Reheat in the microwave for 15-20 seconds or warm in the oven at 300°F for 10 minutes.

Keep cupcakes covered to retain moisture and freshness.

Serving Suggestions

• Pair with vanilla ice cream or whipped cream.
• Serve alongside fresh fruit salad or a tropical smoothie.
• Garnish with toasted coconut flakes or mint leaves.
• Beverage pairing: iced tea, or pineapple mojito.

Perfect for BBQs, potlucks, or even brunch spreads.

FAQ:

Can I make pineapple upside-down cupcakes ahead of time?

Yes! Bake them up to two days in advance and store covered in the fridge. Reheat slightly before serving for best results.

Can I use a pineapple cake mix for this recipe?

Absolutely. Replace the cupcake batter with a pineapple cake mix to save time. Just prepare the topping the same way.

Why are my cupcakes soggy at the bottom?

This can happen if too much juice is added or the topping isn’t properly distributed. Drain the pineapple slices well and use the exact sugar amounts.

What’s the best way to prevent sticking?

Use nonstick spray generously or opt for a silicone muffin tray. Let cupcakes cool slightly before inverting.

How do I make these vegan?

Swap butter for coconut oil, use dairy-free yogurt or applesauce instead of eggs, and double-check your sugar and maraschino cherries are vegan-friendly.

Are these cupcakes similar to the taste of home pineapple upside-down cupcakes?

Yes, this recipe closely mirrors the taste of home pineapple upside-down cupcakes but adds a few modern twists for enhanced flavor and ease.

Can I use fresh pineapple instead of canned?

Yes, but slice it thin and core it properly. You may need to cook it slightly to soften the fibers.

Conclusion

Pineapple Upside-Down Cupcakes are the ultimate throwback treat with a modern, bite-sized upgrade. With their perfect balance of sweet, fruity, and buttery flavors, they’re bound to become your go-to dessert. Whether you’re using a pineapple cake mix or going from scratch, you’ll love the simplicity and joy they bring to every occasion.