pineapple upside down cupcake recipe

Written BySheba G Updated On
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The Best pineapple upside down cupcake recipe

I have been making pineapple upside down cake for years, but turning it into cupcakes was a game changer. These little treats have all the caramelized pineapple and cherry goodness of the classic cake, but they are perfectly portioned and bake much faster. My kids love grabbing one for an after school snack, and I love that they are getting a bit of fruit with their dessert. The pineapple provides vitamin C and manganese, and the whole wheat flour option adds fiber. They are a fun twist on a retro favorite that works for birthdays, potlucks, or just a Tuesday night.

Pineapple Upside Down Cupcakes

4.8 from 1497 votes

Individual pineapple upside down cakes baked in a muffin tin. Each cupcake has a caramelized pineapple ring and cherry on top, with a moist vanilla cake underneath.

Prep Time20 mins
Cook Time22 mins
Resting Time0 mins
Total Time42 mins
Servings: 12Cuisine: InternationalCalories: 280 kcal

🥘Ingredients

For the Topping

1/4 cup unsalted butter, melted
1/2 cup packed brown sugar
12 canned pineapple rings, drained
12 maraschino cherries

For the Cupcakes

1 1/2 cups all purpose flour
1 1/2 teaspoons baking powder
1/4 teaspoon salt
1/2 cup unsalted butter, softened
3/4 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
1/2 cup milk

👨‍🍳Directions

1Preheat oven to 350 degrees F. Line a 12 cup muffin tin with paper liners or spray with nonstick cooking spray.
2In a small bowl, stir together the melted butter and brown sugar. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup.
3Place a pineapple ring in each cup on top of the brown sugar mixture. Put a cherry in the center of each pineapple ring.
4In a medium bowl, whisk together the flour, baking powder, and salt.
5In a large bowl, beat the softened butter and granulated sugar with an electric mixer until light and fluffy, about 2 minutes. Beat in the eggs one at a time, then add the vanilla.
6Add the flour mixture to the butter mixture in three additions, alternating with the milk. Mix just until combined.
7Divide the batter evenly over the pineapple rings in the muffin cups, filling each about 2/3 full.
8Bake for 18 to 22 minutes, until a toothpick inserted into the center of a cupcake comes out clean. Let cool in the pan for 5 minutes, then run a knife around the edges and invert onto a serving platter.

🔧Equipment

12 cup muffin tin
Paper liners or cooking spray
Mixing bowls
Electric mixer or whisk
Measuring cups and spoons
Toothpick for testing

📊Nutrition Facts (per serving)

🔥Calories: 280 kcal🧈Total Fat: 12g💛Saturated Fat: 7g❤️Cholesterol: 60mg🧂Sodium: 180mg🌾Total Carbs: 42g🥦Dietary Fiber: 1g🍬Sugars: 28g🥩Protein: 3g

📝Notes

For a healthier version, use whole wheat pastry flour and reduce the sugar to 1/2 cup. You can also use fresh pineapple slices if you prefer, just make sure they are about 1/4 inch thick.

Watch Video Of How Pineapple Upside Down Cupcakes Works

These pineapple upside down cupcakes are a fun and easy dessert that always gets compliments. They are perfect for birthdays, holidays, or just a weekend treat with the family. I hope you give them a try and enjoy them as much as we do.

❓ Frequently Asked Questions About Pineapple Upside Down Cupcakes

1. Can I use fresh pineapple instead of canned?

Yes, you can. Use fresh pineapple slices that are about 1/4 inch thick. You may need to simmer them in a little sugar water for a few minutes to soften them and bring out sweetness. Canned pineapple is more convenient and gives consistent results.

2. Why did my cupcakes stick to the pan?

This usually happens if you do not let them cool for the full 5 minutes after baking. The brown sugar and butter need that time to set slightly. Also make sure you line the pan well with paper liners or spray with nonstick spray.

3. Can I make these cupcakes gluten free?

Yes, substitute a 1 to 1 gluten free baking flour blend for the all purpose flour. The texture will be slightly different but they will still taste great.

4. How should I store leftover cupcakes?

Store them in an airtight container at room temperature for up to 2 days. You can also refrigerate them for up to 4 days. Reheat in the microwave for 10 to 15 seconds to bring back the caramelized topping.

5. Can I add other fruits to the topping?

Absolutely. You can add a few pecan halves or walnuts alongside the cherry. Some people like to add a thin slice of mango or peach under the pineapple for extra flavor.

Hi, I’m Sheba G, the creator behind **Sheba’s Recipe**, where I share my favorite homemade dishes and easy recipes anyone can try. I love experimenting in the kitchen and helping others enjoy simple, flavorful meals with confidence.

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