Pineapple Upside Down Cupcakes

Alright, these Pineapple Upside Down Cupcakes? They’re sweet, buttery, and totally adorable—everything you love about the classic cake, but baked into individual, single-serve treats. Each one has a caramelized brown sugar pineapple ring and a cherry on top (or really, on the bottom until you flip it!).

I made them for a summer party, and they were gone in a flash. That sticky-sweet topping with moist vanilla cake underneath? Pure sunshine in every bite.

And the best part? They’re easy to make, flip, and serve—no slicing needed. Let’s bake a batch together—these cupcakes are guaranteed to steal the show!

Why You’ll Love This Recipe

• Individually Portioned: No slicing required, which makes serving super easy—especially for events or school lunches.
• Reliable Texture: Because each cupcake is baked separately, you’re less likely to end up with soggy centers or uneven bakes.
• Great Flavor Contrast: The sticky, slightly crisp caramelized topping contrasts beautifully with the soft, buttery vanilla cake.
• Uses Convenient Ingredients: By using a boxed cake mix and canned pineapple, the prep becomes quick and predictable, yet still yields delicious, bakery-worthy results.
• Versatile Presentation: These cupcakes look elegant enough for dinner parties, yet approachable for casual gatherings.

What You Need to Know Before You Start

Prep Time & Cook Time

• Prep Time: 20 minutes
  (This includes draining the pineapple, assembling the topping, and mixing the cake batter.)
• Bake Time: 20 to 25 minutes
  (Keep an eye starting around minute 18—every oven is different.)
• Cooling & Inverting Time: 10 minutes
  (Crucial time to let the caramel set just enough before flipping.)
• Total Time: Approximately 50–55 minutes

Servings

This recipe yields 24 standard cupcakes. If you’re hosting a crowd, this is a great size. For a smaller batch, you can halve the ingredients and use just one 12-cup muffin tin.

Skill Level

This recipe is beginner-friendly, even for those new to baking. The steps are simple, but as with all upside down cakes, timing and technique during inversion (flipping the cupcakes out) matters. If you follow the instructions carefully, you’ll get professional-looking results without a fuss.

Required Kitchen Tools

These basic tools are enough to get great results:

• Two 12-cup muffin tins: Non-stick preferred for easier release.
• Cooking spray: Vital for preventing sticking, especially since these are baked with a sugary syrup on the bottom.
• Mixing bowls: One medium (for the topping) and one large (for cake batter).
• Rubber spatula: Helps spread ingredients gently without overmixing.
• Electric hand mixer or stand mixer: Speeds up the cake batter preparation. You can also whisk by hand if needed.
• Measuring cups and spoons: For accuracy—especially important with cake mix and liquids.
• Cooling rack: Helps cool the cupcakes quickly and evenly after baking.
• Spoon or small ladle: For evenly distributing pineapple and brown sugar mixture.

Ingredients for Pineapple Upside Down Cupcakes

Here’s a detailed look at the ingredients and why each one matters:

• Cooking spray: Non-stick spray is essential for easy release. Since the cupcakes bake with syrup at the bottom, a greased tin prevents tearing when inverted.
• 1/2 cup (1 stick) unsalted butter, melted: Butter forms the rich caramel base with brown sugar. Melted butter spreads evenly and seeps into the cake during baking, adding moisture and flavor.
• 1 1/2 cups packed brown sugar: Dark or light brown sugar works here. It provides a deep molasses sweetness and caramelizes during baking. Pack it well for accurate measurement.
• 24 maraschino cherries: One for each cupcake center. Their bright red color adds contrast and sweetness. Pat them dry slightly to prevent extra moisture.
• 1 (20 oz) can crushed pineapple, drained: Crushed pineapple ensures even layering and flavor in each bite. Reserve the juice—you’ll use it in the cake batter for added pineapple flavor.
• 1 (15.25 oz) box yellow cake mix: A shortcut ingredient that keeps things simple. Choose your preferred brand. The yellow cake’s buttery vanilla flavor complements the fruit and caramel topping.
• Water, vegetable oil, and eggs as listed on the box: Follow your specific cake mix instructions, but replace the water with pineapple juice (up to 1 1/3 cups). This infuses the batter with a light pineapple flavor throughout.
• 1 1/3 cups pineapple juice: Use juice from the crushed pineapple can and top it off with more juice if needed. This replaces plain water in the cake batter, giving it tropical depth.
• Confectioners’ sugar (optional): A light dusting adds a subtle sweetness and finishes the presentation. Wait until the cupcakes are fully cool before dusting.

Variations for Pineapple Upside Down Cupcakes

These cupcakes are simple, but there’s room for creativity depending on your taste and ingredients on hand. Here are a few thoughtful ways to change things up:

• Pineapple Rings Instead of Crushed Pineapple: For a more traditional look, cut pineapple rings into small pieces to fit each muffin cup. This gives more defined fruit layers in each bite.
• Add Coconut: Stir 1/2 cup of shredded sweetened coconut into the cake batter for a tropical touch that pairs perfectly with pineapple.
• Use Spiced Cake Mix: Swap yellow cake for spice cake mix to give warm notes of cinnamon and clove that complement the fruit and brown sugar topping.
• Skip the Cherries: Not a cherry fan? Simply omit them or replace them with dried cranberries or small pieces of mango for a unique flavor twist.
• Add Rum Extract: A few drops of rum extract in the cake batter or pineapple mix can mimic the taste of a pineapple rum cake, without the alcohol.
• Mini Versions: Make these in a mini muffin tin for bite-sized treats. Just reduce the baking time to 10–12 minutes and chop the fruit smaller.

How to Make Pineapple Upside Down Cupcakes – Step-by-Step Instructions

1. Preheat and Prepare Pans

• Preheat your oven to 350°F (175°C).
• Lightly spray two 12-cup muffin tins with non-stick cooking spray. Make sure to coat both the bottom and sides well—this helps the sticky topping release cleanly after baking.

2. Make the Caramel Base

• In a medium bowl, stir together 1/2 cup melted butter and 1 1/2 cups packed brown sugar until it forms a thick, sandy mixture.
• Spoon about 1 tablespoon of this brown sugar mixture into the bottom of each muffin cup. Spread it slightly so it covers the base evenly.

3. Add the Fruit Topping

• Place 1 maraschino cherry in the center of each cup, right on top of the sugar mixture.
• Then, spoon 1 to 1½ tablespoons of drained crushed pineapple around the cherry, gently pressing it down to create an even layer. Avoid overfilling—this will keep the topping neat and prevent spillovers during baking.

4. Make the Cake Batter

• In a large mixing bowl, combine:
  • 1 box yellow cake mix
  • Vegetable oil and eggs as listed on the box
  • 1 1/3 cups pineapple juice (instead of water)
• Beat with an electric mixer (or whisk by hand) for 2 minutes until the batter is smooth, creamy, and slightly thickened.

5. Fill the Muffin Tins

• Spoon the batter over the pineapple mixture in each muffin cup, filling each about 3/4 full. Don’t overfill or the cakes may rise too much and stick.

6. Bake the Cupcakes

• Bake in the preheated oven for 20 to 25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
• The tops should be lightly golden and the batter fully set.

7. Cool and Invert

• Let the cupcakes cool in the tin for exactly 10 minutes. This cooling time helps the sugar settle slightly, making them easier to flip without falling apart.
• Run a small offset spatula or knife around the edge of each cupcake to loosen.
• Place a wire rack or tray over the muffin tin, then quickly and carefully flip the tin over. Tap gently on each cup to release the cupcakes.
• Let them cool upside down for another 10 minutes before serving.

Serving and Decoration

These cupcakes are beautiful right out of the pan, but here are a few extra touches to elevate presentation:

• Dust Lightly with Confectioners’ Sugar: Once the cupcakes are fully cool, a soft dusting of powdered sugar adds a delicate finish. Use a fine-mesh sieve for even coverage.
• Serve Slightly Warm or Room Temperature: While they’re delicious at room temp, these cupcakes are even more flavorful when gently warmed. Microwave for just 8–10 seconds.
• Top with Whipped Cream or Vanilla Ice Cream: A small spoonful of whipped cream or a scoop of vanilla ice cream pairs perfectly with the buttery fruit topping.
• Add a Mint Leaf or Shredded Coconut for Garnish: A tiny green sprig or some toasted coconut on the plate makes these look restaurant-ready.

How to Serve Pineapple Upside Down Cupcakes

Because each cupcake is self-contained, they’re great for all types of occasions:

• Birthday parties and picnics: No cutting, no mess—just hand them out.
• Potlucks and church dinners: They transport well and hold up at room temperature.
• Lunchbox treats or after-school snacks: Sweet but made with fruit, so they feel a bit more wholesome.
• Mini dessert platters: Serve alongside chocolate brownies and lemon bars for a colorful mix.

These cupcakes are especially nice for spring and summer occasions thanks to their light, fruity flavor.

Storing Pineapple Upside Down Cupcakes

Proper storage helps preserve the moisture and flavor of these treats:

• Room Temperature: Keep in an airtight container for up to 2 days. Place a sheet of wax paper between layers if stacking.
• Refrigerator: Store in a sealed container for up to 5 days. Let sit at room temp or microwave briefly before serving to soften the caramel topping.
• Freezer-Friendly: Yes! Wrap each cupcake in plastic wrap, then foil. Store in a freezer-safe bag or container for up to 2 months. Thaw at room temperature or reheat gently.

Tips and Tricks for Success

• Don’t Overfill the Muffin Tins: Stick to 3/4 full. Too much batter will cause overflow and may make it hard to invert cleanly.
• Drain the Pineapple Well: Extra moisture can lead to soggy bottoms or make the sugar syrup runny. Use a strainer or press gently with a spoon to remove juice.
• Let Cool Exactly 10 Minutes Before Flipping: If you flip too soon, the topping might slide off. Wait too long and the sugar may stick. Ten minutes gives the perfect window.
• Use Nonstick Muffin Pans: These make the release much easier, especially since these cupcakes are baked upside down with syrupy fruit.
• Use a Baking Tray or Large Plate for Inversion: This gives you better control and avoids mess when flipping the pan.
• Reserve Some Pineapple Juice: Always save the juice before discarding the can. It makes a big difference in flavor when used in place of water in the cake mix.

Nutrition (Per Cupcake)

Nutrient	Amount
Calories	~210 kcal
Total Fat	8g
Saturated Fat	3.5g
Cholesterol	20mg
Sodium	190mg
Total Carbohydrates	34g
Sugars	23g
Protein	2g
Fiber	<1g
Calcium	4% DV
Iron	6% DV

Note: Nutritional values are approximate and may vary by brand and portion.

Pineapple Upside Down Cupcakes FAQs

Q: Can I use pineapple slices instead of crushed pineapple?
Yes, but you’ll need to cut the slices into smaller pieces to fit each muffin cup. Crushed pineapple distributes more evenly, but slices give a neater, retro look.

Q: Why did my cupcakes stick to the pan?
This usually happens if the pan wasn’t greased well enough or if they were left to cool too long. Use a generous amount of nonstick spray and invert them after 10 minutes—not sooner, not later.

Q: Can I make these in advance?
Yes. These cupcakes stay moist for several days. You can make them a day or two ahead and store them in the fridge. Warm slightly before serving if desired.

Q: Can I freeze pineapple upside down cupcakes?
Absolutely. Once cooled, wrap each cupcake tightly in plastic wrap and foil. Freeze for up to 2 months. Thaw at room temperature or reheat gently.

Q: What if I don’t have pineapple juice?
If you run short on reserved juice, you can supplement with bottled pineapple juice or even orange juice. Avoid using plain water—it dilutes the flavor.

Conclusion

These Pineapple Upside Down Cupcakes are a fun, flavorful way to bring a retro favorite into the modern kitchen. With buttery brown sugar caramel, bright pineapple, and soft yellow cake in perfect individual portions, they’re just right for sharing—or savoring one at a time.

Whether you’re serving them at a party, packing them in a lunchbox, or freezing a few for later, this recipe is approachable, flexible, and consistently rewarding. You don’t need special tools or skills—just a love for fruity, old-fashioned desserts with a tropical twist.