Pineapple Upside Down Cupcakes are a delightful twist on the classic cake, offering individual servings of this iconic dessert. Each cupcake features a caramelized pineapple ring and a cherry at the bottom, enveloped in a moist, buttery cake.

This bite-sized version retains all the charm and flavor of the traditional cake, making it perfect for parties or as a sweet treat. Plus, its upside-down presentation adds a fun and surprising element when served.

Ingredients Needed for This Recipe

1 1/3 cups all-purpose flour
1 cup granulated sugar
1/3 cup unsalted butter, softened

2/3 cup milk
1/4 cup vegetable oil
1 1/2 teaspoons baking powder

1/2 teaspoon vanilla extract
2 large eggs
1/4 teaspoon salt

12 pineapple rings (canned, drained)
12 maraschino cherries
1/2 cup brown sugar

1/4 cup unsalted butter, melted (for the topping)

Instructions for Making Pineapple Upside Down Cupcakes

Preheat your oven to 350°F (175°C) and grease a 12-cup muffin tin.
In a small bowl, mix the melted butter and brown sugar. Divide this mixture evenly among the muffin cups. Place a pineapple ring in each cup, and add a cherry in the center of each ring.

In a large mixing bowl, beat together the 1/3 cup softened butter and granulated sugar until creamy. Add eggs, one at a time, beating well after each addition. Mix in the vanilla extract.
In another bowl, whisk together the flour, baking powder, and salt. Alternately add the flour mixture and milk to the butter mixture, starting and ending with the flour. Mix until just combined, then gently fold in the vegetable oil.
Spoon the batter into the muffin cups, over the pineapple and cherries, filling each about 3/4 full.

Bake for 20-25 minutes, or until a toothpick inserted into the center comes out clean.
Allow the cupcakes to cool in the pan for 5 minutes, then carefully invert them onto a wire rack to cool completely. Be sure to invert while still warm to ensure the caramelized sugar releases from the pan.
Serve and enjoy your Pineapple Upside Down Cupcakes!

These cupcakes are a playful and delicious way to enjoy the vintage charm of pineapple upside down cake. Enjoy baking!

Tips for Perfecting the Recipe

Choose the Right Pineapple: For the best results, use canned pineapple rings. They offer consistency in size and sweetness, ensuring each cupcake has just the right amount of fruit. If you prefer fresh pineapple, make sure it’s ripe and sweet, and cut it into uniform slices for even cooking.

Butter and Brown Sugar Mixture: This mixture creates the caramelized topping that’s iconic to pineapple upside down cake. Make sure the brown sugar and melted butter are well combined to avoid any granular texture. This mixture should be evenly distributed among the muffin cups to ensure each cupcake has a beautifully caramelized top once inverted.

Do Not Overmix the Batter: When combining the wet and dry ingredients, mix until just combined. Overmixing the batter can lead to gluten development, making the cupcakes tough instead of light and fluffy.

Check for Doneness: Since oven temperatures can vary, start checking the cupcakes for doneness at the 20-minute mark. Insert a toothpick into the center of a cupcake; if it comes out clean or with a few moist crumbs, they’re ready. This prevents overbaking, ensuring your cupcakes remain moist.

Inverting the Cupcakes: Invert the cupcakes while they’re still warm. If they cool down too much, the caramelized sugar might harden, making it difficult to release the cupcakes from the pan. Place a wire rack over the muffin tin, and flip it in one swift motion. If any cupcakes stick, gently run a knife around the edges to loosen them.

Making Ahead: If you’re planning to serve these cupcakes for an event, you can prepare the batter a day in advance and store it in the refrigerator. This not only saves time but also allows the flavors to meld together, enhancing the taste.

Serving Suggestions

Whipped Cream: A dollop of whipped cream on top of each cupcake adds a creamy contrast to the caramelized pineapple and cherry. You can flavor the whipped cream with a touch of vanilla or rum for an extra layer of flavor.

Ice Cream: Serving these cupcakes with a scoop of vanilla ice cream transforms them into a decadent dessert, perfect for warm weather or as a comforting treat.

Coconut Shavings: For a tropical twist, sprinkle toasted coconut shavings over the whipped cream or ice cream. This not only adds texture but also complements the pineapple flavor.

Drizzle with Caramel or Rum Sauce: Enhance the caramelized flavor with a light drizzle of caramel sauce. For an adult version, a rum sauce can add a sophisticated note.

Serve at Room Temperature or Warm: These cupcakes are delicious either room temperature or slightly warmed. If you’ve stored them in the refrigerator, a quick 10-second zap in the microwave can bring out their buttery richness.

Storage Tips

Room Temperature: Store the cupcakes in an airtight container at room temperature for up to 2 days. This helps to maintain their moisture and prevents them from drying out.

Refrigerating: For longer storage, place the cupcakes in an airtight container and refrigerate for up to 5 days. The cold can slightly alter the texture, so it’s recommended to bring them to room temperature before serving.

Freezing: Pineapple Upside Down Cupcakes can be frozen for up to 3 months. Wrap each cupcake individually in plastic wrap and then place them in a zip-top freezer bag. Thaw overnight in the refrigerator or at room temperature for a few hours before serving.

Reviving Cupcakes: If the cupcakes have become slightly dry, you can revive them by lightly covering with foil and warming in a preheated oven at 300°F (150°C) for about 10 minutes.

Frequently Asked Questions

Can I make these cupcakes gluten-free?

Yes, you can substitute the all-purpose flour with a gluten-free flour blend. Look for one that’s a 1:1 replacement to ensure the texture remains similar.

Can I use a different fruit?

While pineapple is traditional, you can experiment with other fruits like peaches, pears, or even apples. Just make sure to slice them thinly so they cook through and fit well in the muffin cups.

Why did my cupcakes sink in the middle?

Cupcakes can sink for several reasons, including overmixing the batter, opening the oven door too early during baking, or using expired baking powder. Ensure your baking powder is fresh and follow the recipe carefully to avoid this issue.

Can I make these cupcakes vegan?

Yes, replace the butter with a vegan alternative, use a plant-based milk, and substitute the eggs with a vegan option like flax eggs or a commercial egg replacer.

How do I ensure the cupcakes come out easily from the pan?

Grease the muffin tin well, and consider using cupcake liners for extra insurance. However, the melted butter and sugar mixture usually prevents sticking. Inverting the cupcakes while warm is also key to easy removal.

Pineapple Upside Down Cupcakes

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Ingredients

1 1/3 cups all-purpose flour
1 cup granulated sugar

1/3 cup unsalted butter softened
2/3 cup milk
1/4 cup vegetable oil

1 1/2 teaspoons baking powder
1/2 teaspoon vanilla extract
2 large eggs

1/4 teaspoon salt
12 pineapple rings canned, drained
12 maraschino cherries

1/2 cup brown sugar
1/4 cup unsalted butter melted (for the topping)

Instructions

Preheat your oven to 350°F (175°C) and grease a 12-cup muffin tin.

In a small bowl, mix the melted butter and brown sugar. Divide this mixture evenly among the muffin cups. Place a pineapple ring in each cup, and add a cherry in the center of each ring.
In a large mixing bowl, beat together the 1/3 cup softened butter and granulated sugar until creamy. Add eggs, one at a time, beating well after each addition. Mix in the vanilla extract.
In another bowl, whisk together the flour, baking powder, and salt. Alternately add the flour mixture and milk to the butter mixture, starting and ending with the flour. Mix until just combined, then gently fold in the vegetable oil.

Spoon the batter into the muffin cups, over the pineapple and cherries, filling each about 3/4 full.
Bake for 20-25 minutes, or until a toothpick inserted into the center comes out clean.
Allow the cupcakes to cool in the pan for 5 minutes, then carefully invert them onto a wire rack to cool completely. Be sure to invert while still warm to ensure the caramelized sugar releases from the pan.