Pineapple Upside Down Cupcake Bliss

Name: Pineapple Upside Down Cupcake Bliss
Prep time: 15 min
Cook time: 20 min
Total time: 35 min
Yield: 12 cupcakes
Ingredients: 1/2 cup unsalted butter; 1 cup brown sugar; 1 can pineapple slices in juice, drained; Maraschino cherries; 1 1/2 cups all-purpose flour; 1 cup granulated sugar; 1/2 cup milk; 1/2 cup vegetable oil; 2 large eggs; 2 teaspoons baking powder; 1 teaspoon vanilla extract; 1/4 teaspoon salt

Highlighted under: Pastry & Sweets Corner

I absolutely adore making these Pineapple Upside Down Cupcakes because they combine nostalgia with a delightful twist. Each bite delivers a rich, buttery flavor that's perfectly balanced with the sweetness of caramelized pineapple. The golden mango and cherries give a beautiful presentation, making them perfect for any occasion. Whether I'm hosting a party or simply treating myself, these cupcakes are always a hit. Plus, the mini size adds a fun element, allowing everyone to savor their own little piece of paradise!

Created by

Ethan

Last updated on 2026-02-07T21:06:28.453Z

When I first tried making Pineapple Upside Down Cupcakes, I was skeptical about how the flavors would translate from the classic cake version. However, these mini delights turned out to be a game changer! The combination of caramelized pineapple and soft vanilla cake creates a moist, flavorful experience that’s a step up from typical cupcakes.

One of my favorite tricks is to use brown sugar in the topping, which enhances the caramel flavor. Plus, I’ve learned that letting the cupcakes cool slightly before inverting them helps maintain that perfect shape, so no pineapple gets left behind. Trust me, these cupcakes are worth the extra effort!

Why You'll Love This Recipe
Moist cupcakes with a luscious caramelized pineapple topping
Individual portions make them perfect for sharing
A delightful twist on a classic dessert that sparks nostalgia

Perfecting the Topping

The key to achieving that signature caramelized topping lies in how you prepare the butter and sugar mixture. Make sure to melt the butter over low heat rather than high, as this prevents it from browning too quickly. Once the sugar is stirred in, it should blend smoothly, becoming glossy and slightly thicker. This will ensure that it coats the pineapple and cherries evenly, creating that irresistible caramel layer once baked. If you notice any sugar clumps, continue to stir until fully dissolved.

Using fresh pineapple slices may seem appealing, but canned pineapple is recommended for this recipe since it maintains its shape during baking and is more convenient. If you do opt for fresh pineapple, ensure it’s ripe but not overly soft, as this can lead to mushy cupcakes. Also, consider using a well-drained fruit to avoid excess moisture affecting the batter consistency.

Mastering the Cupcake Batter

When mixing the cupcake batter, it’s essential not to overmix once you add the wet ingredients. Stir gently until just combined; this keeps your cupcakes light and fluffy. The flour should be completely incorporated, but small lumps of flour remaining is actually okay. Overmixing can lead to dense cupcakes, which would detract from the delightful experience of biting into one.

The combination of vegetable oil and milk contributes to the moistness of the cupcakes. Vegetable oil offers a subtle flavor and keeps them tender, while milk adds richness. If you're looking for a dairy-free version, almond milk or oat milk can work well here, maintaining that moisture without compromising flavor.

Ingredients for Pineapple Upside Down Cupcake Bliss

For the Topping

1/2 cup unsalted butter
1 cup brown sugar
1 can pineapple slices in juice, drained
Maraschino cherries

For the Cupcake Batter

1 1/2 cups all-purpose flour
1 cup granulated sugar
1/2 cup milk
1/2 cup vegetable oil
2 large eggs
2 teaspoons baking powder
1 teaspoon vanilla extract
1/4 teaspoon salt

Preparation Instructions

How to Make Pineapple Upside Down Cupcakes

Prepare the Topping

Preheat your oven to 350°F (175°C). In a small saucepan, melt the butter over low heat. Stir in the brown sugar until dissolved. Pour this mixture into a 12-cup muffin tin, distributing evenly. Place a pineapple slice in each cavity and add a cherry to the center.

Make the Cupcake Batter

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

Combine & Bake

Pour the batter over the pineapple slices in the muffin tin, filling each cup about 2/3 full. Bake for 20 minutes or until a toothpick inserted into the center comes out clean. Let cool for 5 minutes.

Invert and Serve

Carefully invert the muffin tin onto a serving platter. Gently tap to release the cupcakes, ensuring the pineapple topping stays intact. Serve warm and enjoy!

Enjoy Your Delicious Treat!

Pro Tips

For an added burst of flavor, sprinkle some shredded coconut on the topping before baking. This gives the cupcakes a delightful texture and enhances the tropical taste.

Storing and Freezing

These Pineapple Upside Down Cupcakes can be stored in an airtight container at room temperature for 2-3 days. However, if you want to keep them fresh for longer, consider refrigerating them, which extends their shelf life to up to a week. Just be aware that refrigeration may slightly alter the texture, making them a bit denser.

If you want to make these cupcakes in advance, they freeze beautifully. After baking and cooling, wrap each cupcake tightly in plastic wrap and place them in a freezer-safe bag. They can be frozen for up to three months. To enjoy them, simply thaw at room temperature for a couple of hours or warm them up briefly in the microwave for a freshly-baked taste.

Serving Suggestions

These delightful cupcakes are perfect as is, but for an extra touch, consider serving them with a scoop of vanilla ice cream or a dollop of whipped cream. The creamy contrast against the caramelized toppings creates a heavenly dessert experience. Additionally, fresh mint leaves can be sprinkled on top for a pop of color and a hint of freshness that complements the sweetness.

For variety, consider adding chopped nuts, like pecans or walnuts, to the topping mixture. This adds a wonderful crunch and extra flavor that pairs well with the soft cupcake texture and syrupy pineapple. You could also experiment with using different fruits, such as peaches or pears, to create seasonal variations of this classic dessert.

Questions About Recipes

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple can be used! Just ensure you slice it evenly and caramelize it before placing it in the muffin tin.

→ How do I store leftover cupcakes?

Store any leftovers in an airtight container at room temperature for up to 3 days. They can also be refrigerated for up to a week.

→ Can I make this recipe gluten-free?

Absolutely! Substitute the all-purpose flour with a gluten-free flour blend to make these cupcakes gluten-free.

→ What other toppings can I use?

You can experiment with different fruits like peaches or strawberries for a unique twist on the classic flavor.