Wander into a tropical dream with these Pineapple Upside Down Cupcakes! Each tender cake is crowned with a gooey brown sugar-butter glaze, caramelized pineapple slices, and juicy maraschino cherries that sparkle like sunset jewels. Light, moist vanilla-scented batter bubbles up around the fruit, soaking in all that sweet, tangy magic. Perfect for brunches, parties, or cheeky midnight cravings, they bring sunshine to your taste buds. Whip them up in no time—melt your butter, sprinkle on brown sugar, and top with pineapple and cherries before baking. Golden, adorable, and bursting with flavor, they’re an irresistibly fun twist on a classic treat!
Table of Contents
Why You’ll Love This Pineapple Upside Down Cupcakes
- Deliciously moist and fluffy texture that melts in your mouth.
- Sweet and tangy pineapple paired with rich caramel flavors.
- Perfect individual servings for easy sharing and enjoyment.
- Fun and nostalgic twist on a classic dessert that brings joy to any occasion.
Recipe Snapshot
Feature | Details |
---|---|
Category | Dessert |
Cuisine | American |
Prep Time | 15 minutes |
Cook Time | 20 minutes |
Extra Time | 5 minutes (cooling) |
Total Time | 40 minutes |
Dietary | Vegetarian |
Serves | 12 |
Best Served | Warm and topped with whipped cream! |
Ingredients
Here’s what you’ll need to whip up these delightful Pineapple Upside Down Cupcakes!

- 1/4 cup unsalted butter – melted
- 1/2 cup brown sugar – packed
- 12 maraschino cherries – halved
- 1 cup pineapple chunks – or crushed pineapple, drained
How to Make Pineapple Upside Down Cupcakes
Get ready to indulge in a delightful treat! These Pineapple Upside Down Cupcakes are not only delicious but also fun to make. With a preparation time of about 15 minutes and a cooking time of 18–22 minutes, you’ll have these sweet delights ready in no time. Allow for a quick cooling time of 5 minutes before serving. Let’s dive in!

Step 1: Preheat the Oven
Preheat your oven to 350°F (175°C). This ensures your cupcakes bake evenly and come out perfectly fluffy.
Step 2: Prepare the Topping
Melt 1/4 cup of unsalted butter in a bowl. Stir in 1/2 cup of packed brown sugar until the mixture is smooth and well combined.
Step 3: Assemble the Cups
Spoon a teaspoon of the brown sugar mixture into the bottom of each muffin cup. This will create a sweet base for your cupcakes.
Step 4: Add the Fruit
Place pineapple chunks around the edge of each cup and add a halved maraschino cherry in the center. This will make your cupcakes look beautiful!
Step 5: Prepare the Batter
Prepare your favorite yellow or vanilla cupcake batter. Pour it evenly over the fruit layers in each muffin cup, covering them completely.
Step 6: Bake the Cupcakes
Bake the cupcakes in the preheated oven for 18–22 minutes. Check with a toothpick; it should come out clean when they are done.
Step 7: Cool and Invert
Let the cupcakes cool for 5 minutes in the pan. Then, carefully invert them onto a tray so the topping side is up. Enjoy your delicious Pineapple Upside Down Cupcakes!
Pro Tips for Making Pineapple Upside Down Cupcakes
- Opt for fresh pineapple for a vibrant flavor.
- Ensure the butter is fully melted for a smooth topping.
- Distribute the cherries evenly for a beautiful presentation.
- Let the cupcakes cool slightly before inverting for easier removal.
- Experiment with coconut milk for a tropical twist in the batter.
How to Serve this Pineapple Upside Down Cupcakes
- Serve warm with a scoop of vanilla ice cream on top.
- Drizzle with caramel sauce for an extra sweet touch.
- Pair with a refreshing coconut milkshake.
- Garnish with toasted coconut flakes for added texture.
- Enjoy with a cup of herbal tea for a cozy afternoon treat.
Make Ahead and Storage
You can make these delightful cupcakes ahead of time and store them properly:
Storing Pineapple Upside Down Cupcakes Leftovers
- Allow cupcakes to cool completely.
- Store in an airtight container at room temperature for up to 2 days.
- For longer storage, refrigerate for up to a week.
Freezing Pineapple Upside Down Cupcakes
- Wrap each cupcake tightly in plastic wrap.
- Place wrapped cupcakes in a freezer-safe bag or container.
- Freeze for up to 3 months for best quality.
Reheating Pineapple Upside Down Cupcakes
- Thaw cupcakes in the refrigerator overnight if frozen.
- Reheat in the microwave for 10-15 seconds for a warm treat.
- For a crispy top, reheat in the oven at 350°F (175°C) for 5-7 minutes.

Pineapple Upside Down Cupcakes
Equipment
- 1 Muffin Tin For baking the cupcakes.
- 1 Mixing bowl For mixing the batter.
- 1 Whisk For mixing ingredients.
Ingredients
Topping
- 1/4 cup unsalted butter Melted
- 1/2 cup brown sugar Packed
Fruit
- 12 pieces maraschino cherries Halved
- 1 cup pineapple chunks Or crushed pineapple, drained
Instructions
Preparation
- Preheat your oven to 350°F (175°C). This ensures your cupcakes bake evenly and come out perfectly fluffy.
- Melt 1/4 cup of unsalted butter in a bowl. Stir in 1/2 cup of packed brown sugar until the mixture is smooth and well combined.
- Spoon a teaspoon of the brown sugar mixture into the bottom of each muffin cup. This will create a sweet base for your cupcakes.
- Place pineapple chunks around the edge of each cup and add a halved maraschino cherry in the center. This will make your cupcakes look beautiful!
- Prepare your favorite yellow or vanilla cupcake batter. Pour it evenly over the fruit layers in each muffin cup, covering them completely.
- Bake the cupcakes in the preheated oven for 18–22 minutes. Check with a toothpick; it should come out clean when they are done.
- Let the cupcakes cool for 5 minutes in the pan. Then, carefully invert them onto a tray so the topping side is up. Enjoy your delicious Pineapple Upside Down Cupcakes!
Notes
Nutrient | Amount per Serving |
---|---|
Calories | 200 |
Fat | 8g |
Protein | 2g |
Carbs | 30g |
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FAQs
Here’s a helpful FAQ about this recipe:
1. Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple can add a delightful flavor to your cupcakes. Just make sure to cut it into small chunks and drain any excess juice before using it in the recipe.
2. How do I store leftover cupcakes?
To keep your Pineapple Upside Down Cupcakes fresh, store them in an airtight container at room temperature for up to 2 days. If you want to keep them longer, you can refrigerate them for up to a week.
3. Can I make these cupcakes gluten-free?
Yes, you can easily make these cupcakes gluten-free by substituting all-purpose flour with a gluten-free flour blend. Just ensure that the blend you choose is suitable for baking to achieve the best texture.
4. What can I use instead of maraschino cherries?
If you prefer not to use maraschino cherries, you can substitute them with fresh cherries or even blueberries for a different twist. Just make sure to adjust the sweetness if needed!
Final Thoughts
Get ready to indulge in the delightful nostalgia of Pineapple Upside Down Cupcakes! With their sweet, caramelized topping and fluffy cake, these treats are a breeze to make and a joy to share. So gather your loved ones, whip up a batch, and savor every bite of this tropical delight. Happy baking!