Name: Mini Pineapple Upside-Down Cupcakes Recipe
Prep time: 15 min
Cook time: 25 min
Total time: 40 min
Cuisine: American
Ingredients: 2 tablespoons unsalted butter, melted; 4 tablespoons brown sugar; 4 pineapple slices (from canned, in juice), cut into thirds; 12 maraschino cherries; 1 cup all-purpose flour; 1 teaspoon baking powder; 1⁄4 teaspoon salt; 1⁄2 cup granulated sugar; 1⁄4 cup unsalted butter, softened; 2 large eggs; 1⁄2 cup milk; 1 teaspoon vanilla extract

I still remember the first time I made these Mini Pineapple Upside-Down Cupcakes—the warm, golden caramelized edges, the juicy pineapple ring, and that glossy maraschino cherry right in the center. It was love at first bite. These individual treats are the perfect little spin on the classic pineapple upside-down cake. They’re fun, eye-catching, and most importantly, incredibly delicious. Each one has that familiar combination of sweet, buttery cake and tangy fruit, but in a bite-sized form that’s ideal for parties, brunches, or a late-night craving.

I love how easy they are to whip up, too. No need for slicing a big cake or fussing over presentation—these cupcakes do all the work themselves. You flip them out of the tin, and voilà! Each one is already perfectly decorated with caramelized pineapple and a cherry that makes them look like you spent hours. Whether you’re making these for a holiday dessert table or just to surprise someone you love, they always disappear quickly. And let’s be honest—who can resist a mini cake?

Why You’ll Love This Mini Pineapple Upside-Down Cupcakes Recipe

These mini cupcakes offer everything you love about a traditional pineapple upside-down cake, but with more convenience and charm. The caramelized brown sugar base gives them a rich depth of flavor, while the pineapple adds tropical freshness. Plus, their size makes them perfect for portion control (or not, depending on your willpower!).

Perfect for parties – easy to serve, no slicing required.
Faster baking than a full cake.
Fun to make with kids—they’ll love adding the cherries!
Great make-ahead dessert that holds up beautifully overnight.
Elegant presentation without extra effort.

What Kind of Pineapple Should I Use for Mini Pineapple Upside-Down Cupcakes?

For these mini cupcakes, canned pineapple slices are your best bet. They’re uniform in size, which makes it easier to cut them down to fit into the muffin tins. Look for the ones packed in juice—not syrup—so they aren’t overly sweet. If you prefer fresh pineapple, go for it! Just make sure to cut thin, even slices and remove the core, as it can be a bit tough.

And don’t forget the maraschino cherries—they’re not just for looks. That little burst of cherry sweetness right in the center is what makes these cupcakes really pop.

Options for Substitutions

You’ve got plenty of room to play with this recipe. Here are a few tasty ways to switch things up while keeping that nostalgic pineapple upside-down flavor intact:

Butter Substitute: Use coconut oil for a tropical twist and dairy-free option.
Brown Sugar Alternative: Coconut sugar or maple syrup can work if you’re avoiding refined sugars.
Flour Swap: A gluten-free all-purpose flour blend works great for those with sensitivities.
Egg Replacement: Flax eggs (1 tbsp ground flax + 2.5 tbsp water per egg) work well if you’re baking vegan.
Maraschino Cherry Alternative: Try a fresh cherry or even a raspberry if you want to avoid food dyes.
Cake Mix Shortcut: If you’re short on time, a boxed yellow cake mix can absolutely work—just doctor it up with a little vanilla or pineapple juice for more flavor.

Keep in mind that small adjustments might slightly change the texture, but the end result will still be delicious and eye-catching.

Ingredients for This Mini Pineapple Upside-Down Cupcakes Recipe

Each ingredient plays an important role in creating these adorable, flavor-packed mini treats. Here’s what you’ll need and why it matters:

Unsalted Butter
Used to create that golden, buttery base under the pineapple—essential for richness and caramelization.
Brown Sugar
Helps create that sticky-sweet glaze that caramelizes beautifully at the bottom (which becomes the top!) of each cupcake.
Canned Pineapple Slices
Juicy, sweet, and tender, these are trimmed to fit each muffin cup and provide that signature tropical flavor.
Maraschino Cherries
Bright, sweet, and slightly tart, they sit right in the middle of each pineapple slice for a pop of color and flavor.
All-Purpose Flour
Forms the base of the cupcake batter, giving it structure and a soft crumb.
Baking Powder
A leavening agent to help the cupcakes rise and become light and fluffy.
Salt
Just a pinch brings balance and enhances the sweetness without overpowering it.
Granulated Sugar
Sweetens the cupcake batter while keeping the texture smooth and tender.
Eggs
Bind the ingredients together and help give the cupcakes their soft, moist interior.
Milk
Adds moisture and helps create a smooth batter; whole milk is ideal for richness.
Vanilla Extract
Adds depth and rounds out the tropical flavors with a hint of warmth.

Each component works together to create cupcakes that are moist, flavorful, and beautifully caramelized on top. Once you flip them, they practically glow.

Step 1: Prepare the Pineapple and Cherries

Drain the canned pineapple slices and maraschino cherries. Cut each pineapple ring into thirds so they fit nicely into the muffin cups. Set aside while you prep the rest.

Step 2: Grease the Muffin Pan Generously

Use softened butter or nonstick spray to coat each cup of your muffin tin very well. This is key for an easy release after baking.

Step 3: Create the Caramel Base

Add about ½ teaspoon of melted butter into the bottom of each muffin cup. Then sprinkle 1 teaspoon of brown sugar on top of the butter. Place a piece of pineapple into each cup, and gently press a maraschino cherry in the center.

Step 4: Mix the Dry Ingredients

In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.

Step 5: Cream the Butter and Sugar

In a large mixing bowl, beat the softened butter and granulated sugar together until light and fluffy. This gives the cupcakes a tender texture.

Step 6: Add Eggs and Vanilla

Beat in the eggs one at a time, mixing well after each. Add the vanilla extract and stir to combine.

Step 7: Combine Dry and Wet Ingredients

Alternate adding the dry ingredients and milk to the butter mixture, starting and ending with the dry. Mix just until smooth—don’t overdo it.

Step 8: Fill the Muffin Tins

Spoon the batter over the pineapple and cherries, filling each muffin cup about ¾ full.

Step 9: Bake

Place the pan in a preheated oven at 350°F (175°C) and bake for 20–25 minutes, or until the tops are golden and a toothpick comes out clean.

Step 10: Cool and Flip

Let the cupcakes cool in the pan for 5 minutes. Then, place a baking sheet or large tray over the muffin tin and quickly flip it to release the cupcakes. Lift off the tin slowly, and let the cupcakes cool completely.

How Long to Cook the Mini Pineapple Upside-Down Cupcakes

These cupcakes bake beautifully in just 20 to 25 minutes at 350°F (175°C). You’ll know they’re done when the tops are golden brown, slightly springy to the touch, and a toothpick inserted into the center comes out clean (just make sure to test the cake part, not the pineapple). Let them rest in the pan for about 5 minutes before flipping—this allows the caramelized sugar to set slightly but still release easily.

Tips for Perfect Mini Pineapple Upside-Down Cupcakes

Use a nonstick muffin pan and grease generously—butter or spray all the way up the sides to help them release smoothly after flipping.
Cut the pineapple rings to fit perfectly into your muffin tin. Too large, and they’ll crowd the batter; too small, and you’ll lose that iconic look.
Press the cherry gently into the center of the pineapple to keep it in place while baking.
Don’t overmix the batter. Overmixing leads to dense cupcakes. Stir just until the ingredients are combined.
Cool just the right amount before flipping—about 5 minutes. Too soon and they may fall apart; too late and the caramelized sugar could harden and stick.
Place a rimmed baking sheet underneath when flipping to catch any extra syrup that may run off.
Serve slightly warm if possible—these cupcakes are extra delicious when the caramel glaze is still soft and glossy.

Watch Out for These Mistakes While Cooking

Even a simple recipe like mini pineapple upside-down cupcakes has its sneaky pitfalls. Here’s what to avoid:

Not greasing the muffin tin enough: This is the #1 mistake. Without enough grease, your cupcakes will stick and tear apart when flipping.
Using syrup-packed pineapple: This can make the cupcakes too sweet and soggy. Pineapple in juice is better balanced and less heavy.
Overfilling the cups with batter: Aim for about ¾ full—any more and they’ll rise too much and overflow.
Letting them sit too long before flipping: The brown sugar will harden, making them stick to the pan. 5 minutes is the sweet spot.
Using cold ingredients: Room temperature butter, eggs, and milk will blend more evenly for a better-textured batter.
Skipping the tap-and-shake test before baking: Lightly tap the muffin tin to settle the batter evenly over the pineapple before it goes in the oven.

What to Serve With Mini Pineapple Upside-Down Cupcakes?

These mini treats pair beautifully with both sweet and savory companions. Here are a few standout ideas:

Whipped Coconut Cream

A light, dairy-free topping that complements the tropical pineapple flavor.

Vanilla Ice Cream

Classic and creamy—especially good if you serve the cupcakes warm!

Fresh Berries

Add raspberries, blueberries, or sliced strawberries on the side for a pop of color and freshness.

Sparkling Pineapple Mocktail

Keep the tropical vibes going with a chilled drink made from pineapple juice, lime, and soda water.

Coffee or Espresso

The sweet, buttery richness of the cupcakes pairs wonderfully with a bold cup of coffee.

Crispy Bacon or Sausage Links

If you’re serving them as part of a brunch, a little savory on the side balances the sweetness.

Grilled Pineapple Slices

Go full-on pineapple paradise with warm, caramelized grilled pineapple alongside the cupcakes.

Greek Yogurt Parfait

Layer some tangy yogurt with granola and fruit to create a brunch plate with contrast and texture.

Storage Instructions

These Mini Pineapple Upside-Down Cupcakes store surprisingly well, making them perfect for prepping ahead.

Room Temperature: If you plan to eat them within a day, keep them in an airtight container at room temp. Just make sure they’re completely cooled before storing to prevent condensation.
Refrigerator: For longer storage (up to 4 days), place them in a sealed container and refrigerate. The flavor develops even more overnight, though the texture may firm up slightly—just let them come to room temperature before serving, or give them a 10–15 second microwave warm-up.
Freezer: Yes, you can freeze them! Wrap each cupcake tightly in plastic wrap, then store in a freezer-safe bag or container. Freeze for up to 2 months. Thaw overnight in the fridge or on the counter, then warm gently before serving.

Estimated Nutrition (Per Cupcake – Approximate)

These numbers are estimates and may vary based on exact ingredient brands and portion sizes.

Calories: 180
Fat: 7g
Saturated Fat: 4g
Cholesterol: 35mg
Sodium: 100mg
Carbohydrates: 28g
Fiber: 0.5g
Sugar: 18g
Protein: 2g

These cupcakes are indulgent but portion-controlled—just enough to satisfy your sweet tooth without going overboard.

Frequently Asked Questions

What kind of muffin pan should I use?

A standard 12-cup nonstick muffin pan works best. Nonstick is important because of the caramelized sugar base—silicone pans tend to be too flexible and don’t release as cleanly.

Can I make these cupcakes ahead of time?

Yes! You can make them a day in advance and store them in an airtight container. They taste great the next day and are even easier to unmold when fully cooled.

Can I use fresh pineapple instead of canned?

Absolutely. Just slice it thinly and remove the core from each slice. Keep in mind that fresh pineapple has less moisture and may caramelize slightly faster.

What if I don’t have maraschino cherries?

You can skip them or use alternatives like fresh cherries, raspberries, or even dried cranberries for a different twist.

Can I make these in a mini muffin pan?

You can! Just cut the pineapple and cherries into smaller pieces. Reduce the bake time to around 12–15 minutes, and watch closely.

How do I flip the cupcakes without making a mess?

Let them cool for 5 minutes, place a large tray or cutting board over the muffin tin, and quickly flip. Use a kitchen towel to protect your hands and hold everything in place.

Why are my cupcakes sticking to the pan?

Most likely, it’s due to not greasing enough or letting them sit too long before flipping. Always grease generously and flip within 5–7 minutes of coming out of the oven.

Can I double the recipe?

Yes, and it’s perfect for parties. Just bake in batches or use two muffin pans. Make sure you evenly distribute the caramel base and fruit.

Conclusion

Mini Pineapple Upside-Down Cupcakes are the kind of dessert that feels nostalgic yet fresh, elegant yet playful. I’ve made these for birthdays, brunches, and casual weekend treats, and they never fail to draw a crowd. They come together quickly, look beautiful flipped out of the pan, and taste like a tropical vacation in cupcake form. If you’re looking for an easy, fun, and foolproof dessert that hits all the right notes—this is it.

Ready to impress with minimal stress? These cupcakes have your back.