Pineapple Upside Down Cupcake Bliss

Name: Pineapple Upside Down Cupcake Bliss
Prep time: 20 min
Cook time: 25 min
Total time: 45 min
Yield: 12 cupcakes
Ingredients: 1 can (8 oz) pineapple slices in juice, drained; 1/2 cup brown sugar; 1/4 cup unsalted butter; 1 1/2 cups all-purpose flour; 1 cup granulated sugar; 1/2 cup unsalted butter, softened; 2 large eggs; 1 tsp vanilla extract; 1/2 cup milk; 2 tsp baking powder; 1/4 tsp salt

Highlighted under: Easy Baking Recipes

I absolutely adore these Pineapple Upside Down Cupcakes! Each bite delivers a delightful combination of sweetness with a hint of tang from the pineapple. The moist, buttery cake contrasts beautifully with the caramelized pineapple topping. These cupcakes are perfect for gatherings or when I need a little pick-me-up. They are uncomplicated to make, yet they never fail to impress. With a simple recipe, you can create an indulgent treat that tastes like a celebration, even on an ordinary day.

Created by

Anna

Last updated on 2026-02-07T22:02:28.868Z

When I first experimented with these Pineapple Upside Down Cupcakes, I was amazed at how effortlessly the flavors melded together. The initial idea came from a traditional dessert my grandmother made, but putting it into cupcake form really made it special. The caramelization of the pineapple is crucial for that rich sweetness, and I always ensure to use unsalted butter for the cake for the perfect balance.

One of my favorite tips is to let the cupcakes cool slightly before flipping them over. This gives the caramel a chance to set while the cupcakes retain their moisture. The surprise of discovering the perfectly rounded pineapple slice on top is always a crowd-pleaser. They'll have everyone coming back for more!

Why You'll Love These Cupcakes
Delightfully moist cake infused with tropical flavors
Beautiful presentation with the caramelized pineapple
Fun and easy to make, perfect for any occasion

Mastering the Perfect Topping

The topping of your Pineapple Upside Down Cupcake is what sets these treats apart from the ordinary. When melting the butter and brown sugar mixture, ensure it reaches a bubbly, glossy consistency before pouring it into the cupcake pan. This not only helps in caramelization but also creates a deeper, richer flavor. Be sure to work quickly; even a moment too long on the heat can turn the mixture overly dark and bitter, which may affect the overall taste of your cupcakes.

Using ripe, juicy pineapple is crucial for achieving that signature tangy sweetness. If fresh pineapple is available, consider slicing it instead of using canned. However, be sure to drain it well to avoid excess moisture that could make the batter soggy. For an extra flavor kick, try adding a sprinkle of cinnamon to the brown sugar mixture; it adds a subtle warmth that complements the pineapple beautifully.

Cupcake Batter Secrets

Getting the texture of your cupcake batter just right is vital for achieving that light, moist cupcake. When creaming the butter and sugar, mix until it reaches a pale, fluffy state—this usually takes about 3-5 minutes with an electric mixer. This aeration is key, as it results in a cupcake that rises beautifully and maintains a tender crumb. If you're using room temperature ingredients, remember they mix more uniformly, contributing to an even texture throughout the batter.

For a dairy-free option, you can substitute the milk with almond milk or coconut milk to retain the moistness of your batter. Be cautious when measuring flour; using the spoon-and-level method is the best practice to avoid dense cupcakes. Too much flour can lead to a heavy texture, while too little might prevent them from rising properly. Keep a steady hand, and you'll be rewarded with cupcakes that are both delicious and light.

Ingredients for Pineapple Upside Down Cupcakes

For the Topping

1 can (8 oz) pineapple slices in juice, drained
1/2 cup brown sugar
1/4 cup unsalted butter

For the Cupcake Batter

1 1/2 cups all-purpose flour
1 cup granulated sugar
1/2 cup unsalted butter, softened
2 large eggs
1 tsp vanilla extract
1/2 cup milk
2 tsp baking powder
1/4 tsp salt

Instructions

Prepare the Topping

Preheat your oven to 350°F (175°C). In a saucepan over medium heat, melt the butter and brown sugar until smooth. Pour this mixture into the bottom of a cupcake pan, ensuring it evenly coats the bottom. Place one pineapple slice in each cup.

Make the Batter

In a mixing bowl, cream together the softened butter and granulated sugar until fluffy. Add in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract. In another bowl, mix the flour, baking powder, and salt. Gradually add this dry mix to the wet ingredients, alternating with milk, until just combined.

Bake and Cool

Spoon the batter over the pineapple in each cupcake cup, filling each about 3/4 full. Bake for 20-25 minutes until a toothpick inserted into the center of a cupcake comes out clean. Allow the cupcakes to cool for 5-10 minutes before flipping them onto a cooling rack.

Pro Tips

For an extra touch, try adding a sprinkle of toasted coconut on top once cooled for added flavor and texture.

Storing and Serving

These Pineapple Upside Down Cupcakes store well, making them ideal for batch baking. Once completely cooled, place them in an airtight container and keep them at room temperature for up to 3 days. If you want to enjoy them longer, consider freezing; wrap each cupcake tightly in plastic wrap and place them in a freezer-safe bag. They can last for up to three months, and all you need to do is let them thaw at room temperature before serving.

When it comes to serving, these cupcakes shine in their individual form. For an added touch, drizzle a bit of extra caramel sauce over the top before presenting them to guests. You can also pair them with a scoop of vanilla ice cream for a delightful dessert experience. If you're feeling adventurous, try experimenting with different fruit toppings, such as peaches or cherries, to change up the flavor profile while keeping the same cupcake base.

Troubleshooting Common Issues

If your cupcakes are sinking in the middle, it often means they were underbaked or that the oven temperature was too low. Always preheat your oven thoroughly, and use an oven thermometer to verify the actual temperature. Bake until a toothpick inserted in the center comes out clean or with a few crumbs, indicating they are done. Additionally, avoid opening the oven door too soon, as this can disrupt the rising process.

Sometimes the caramel topping can be too sticky or overly hard. If you find the topping is difficult to release when flipping, you might not have used enough butter or sugar in the mixture. Make sure the sugar is melted uniformly—if it’s too dark, it can harden upon cooling. If you experience this, heating the pan slightly before inverting can help loosen the cupcakes.

Questions About Recipes

→ Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple will add a lovely flavor, just ensure you slice it thinly.

→ What can I substitute for the butter?

You can use coconut oil or a dairy-free butter substitute if you're looking for a dairy-free option.

→ How do I store leftover cupcakes?

Store them in an airtight container at room temperature for up to three days, or refrigerate for longer freshness.

→ Can I freeze these cupcakes?

Yes, you can freeze them! Just make sure to wrap them well to prevent freezer burn.