Pineapple Upside-Down Cupcakes

Name: Pineapple Upside-Down Cupcakes
Prep time: 15 min
Cook time: 25 min
Total time: 40 min
Yield: 12 cupcakes
Ingredients: 1 can (8 oz) pineapple slices; 1/4 cup unsalted butter; 1/3 cup brown sugar; Maraschino cherries (optional); 1 1/2 cups all-purpose flour; 1/2 cup granulated sugar; 2 tsp baking powder; 1/4 tsp salt; 1/2 cup milk; 1/3 cup vegetable oil; 1 tsp vanilla extract; 1 large egg

Highlighted under: Artisanal Baking Recipes

I love making Pineapple Upside-Down Cupcakes as they are the perfect blend of fruity goodness and cake. The caramelized pineapple on top adds a delightful sweetness that pairs beautifully with the soft, fluffy batter. Each bite is a burst of flavor, and I enjoy watching my guests’ faces light up as they experience this unique dessert. They’re so easy to make and perfect for any gathering, making them a favorite in my baking repertoire.

Created by

Anna

Last updated on 2026-02-13T15:54:18.740Z

When I first made Pineapple Upside-Down Cupcakes, I was amazed at how the delicate sweetness of pineapple complements the fluffy cake. The process of caramelizing the pineapple slices before baking brings out their natural juices, transforming them into tender bits of perfection. I also discovered that using brown sugar in the cupcake batter enhances the flavor and creates a lovely golden hue.

One tip that makes these cupcakes a hit is adding a hint of vanilla extract to the batter. It elevates the flavor profile and balances out the sweetness from the pineapple. Not only do I love these cupcakes for their taste, but they also look stunning on a dessert table!

Why You'll Love These Cupcakes
Delicious caramelized pineapple topping adds a tropical touch
Soft and moist cupcakes make for a delightful texture
Perfectly portioned for individual servings, ideal for gatherings

Mastering the Pineapple Topping

The caramel topping is what truly sets these cupcakes apart. When melting the butter, ensure it doesn’t brown; you want a smooth, creamy base for the brown sugar. Stir until the mixture is completely combined and a glossy consistency is achieved. If you find your sugar is taking too long to dissolve, increase the heat slightly, but be careful not to let it burn. Pour this mixture evenly across the cupcake pan to ensure every bite is equally delicious.

Using canned pineapple makes the process quick and consistent, but if you're feeling adventurous, fresh pineapple can elevate the flavor even further. Cut the fresh pineapple into rings, and slightly grill or sauté them for a few minutes to bring out their natural sweetness before layering them in the cupcake tin. This not only enhances the taste but also offers a firmer texture that holds up beautifully during baking.

Perfecting the Cupcake Batter

When combining the dry ingredients, use a whisk to aerate the flour and ensure there are no lumps left behind. This step is crucial for achieving a light and fluffy cupcake. After mixing the wet and dry ingredients, be careful not to over-mix the batter. Stop as soon as you see no dry flour; it’s okay if a few small lumps remain. Overworking the batter can lead to a dense cupcake, which contradicts the airy texture we’re aiming for.

If you’re looking for dietary swaps, you can substitute the all-purpose flour with a gluten-free blend; just ensure it’s one that contains xanthan gum to mimic the elasticity of regular flour. For a dairy-free option, non-dairy milk like almond or oat milk can easily replace cow’s milk without compromising flavor. These substitutions make the recipe accessible for a wider audience while maintaining the core experience of a pineapple upside-down cupcake.

Ingredients

Gather the following ingredients:

For the Pineapple Topping

1 can (8 oz) pineapple slices
1/4 cup unsalted butter
1/3 cup brown sugar
Maraschino cherries (optional)

For the Cupcake Batter

1 1/2 cups all-purpose flour
1/2 cup granulated sugar
2 tsp baking powder
1/4 tsp salt
1/2 cup milk
1/3 cup vegetable oil
1 tsp vanilla extract
1 large egg

Mix well and set aside.

Instructions

Follow these simple steps to make your cupcakes:

Prepare the Pineapple Topping

Preheat your oven to 350°F (175°C). In a small saucepan, melt the butter over medium heat. Stir in the brown sugar until dissolved. Remove from heat and pour into the bottom of a cupcake pan. Arrange the pineapple slices on top of the brown sugar mixture and place a cherry in the center of each pineapple ring if desired.

Make the Cupcake Batter

In a mixing bowl, combine the flour, granulated sugar, baking powder, and salt. In another bowl, whisk together the milk, vegetable oil, vanilla extract, and egg. Gradually add the wet ingredients to the dry ingredients and mix until just combined.

Bake the Cupcakes

Spoon the batter over the pineapple in the cupcake pan, filling each cup about 2/3 full. Bake in the preheated oven for 20-25 minutes, or until a toothpick inserted into the center comes out clean. Allow to cool for a few minutes before inverting onto a serving platter.

Enjoy your delightful Pineapple Upside-Down Cupcakes!

Pro Tips

For an extra flavor twist, consider adding chopped walnuts or pecans to the batter for added crunch.

Storage and Make-Ahead Tips

These cupcakes are best enjoyed fresh, but if you need to prepare them ahead of time, store them in an airtight container at room temperature for up to two days. If you plan to keep them longer, refrigerate them, which can extend their freshness for about a week. Just be sure to bring them to room temperature before serving to fully appreciate their taste and texture.

If you're thinking of freezing these cupcakes, it's highly recommended to do so without the pineapple topping. Bake and cool the cupcakes completely, then wrap them tightly in plastic wrap and foil. They can stay frozen for up to three months. When you're ready to enjoy them, simply thaw at room temperature and prepare a fresh batch of pineapple topping to maintain that caramelized flavor.

Serving Suggestions and Variations

To elevate your presentation, consider serving these cupcakes with a scoop of vanilla ice cream or a dollop of whipped cream on the side. The creamy elements provide a wonderful contrast to the sweetness and fruitiness of the pineapple topping, making the dessert even more luxurious. For a fun twist, sprinkle some toasted coconut flakes over the frosting for an added texture and tropical flair.

If you want to experiment with flavors, try incorporating a teaspoon of coconut extract into the cupcake batter for an unexpected tropical twist. You could also use ripe mango slices instead of pineapple for a different take on this classic recipe. Just remember to adjust the baking time if you’re making larger or smaller cupcakes to ensure even cooking throughout.

Questions About Recipes

→ Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple is a great alternative, just make sure to cut it into thin, even slices.

→ How do I store leftover cupcakes?

Store them in an airtight container at room temperature for up to 3 days or in the fridge for up to a week.

→ Can I make these cupcakes ahead of time?

Yes, you can make the cupcakes a day in advance and keep them covered. Just add the caramelized topping just before serving.

→ What's the best way to serve these cupcakes?

Serve them slightly warm for the best flavor, or at room temperature with a scoop of vanilla ice cream on the side.