Pineapple Upside Down Cupcakes – Easy & Quick

Mini Tropical Cakes Topped with Caramelized Pineapple, Cherries, and Buttery Brown Sugar Goodness

🎉 Introduction

There’s something magical about a dessert that flips upside down and still comes out absolutely stunning. These Pineapple Upside Down Cupcakes are the individual-sized spin on the classic cake — complete with golden caramelized pineapple, juicy maraschino cherries, and a moist vanilla coconut cupcake base.

They’re everything you love about summer: tropical flavor, vibrant color, and sweet nostalgia. Best of all? They’re quick to make, easy to serve, and don’t require any fancy decorating. These cupcakes bake up tender and light, with the perfect balance of fruit and cake in every bite.

From backyard BBQs to holiday dessert trays, these easy pineapple cupcakes are the kind of recipe that makes everyone think you baked all day — but you didn’t.

🧰 Equipment Needed

Before you start flipping cupcakes, make sure you have the following:

• 12-cup muffin pan
• Non-stick cooking spray or butter for greasing
• Mixing bowls (large and medium)
• Hand mixer or stand mixer
• Rubber spatula
• Measuring cups and spoons
• Knife and cutting board
• Small saucepan (optional for melting butter/sugar)
• Cooling rack

🛒 Ingredients

🍋 Fruits and Vegetables

• 6 pineapple rings, halved
• 1 tsp lemon juice (optional, brightens flavor)

🥚 Fresh Products

• 2 large eggs

🍬 Pantry Items and Spices

• 1½ cups all-purpose flour
• 1½ tsp baking powder
• ¾ cup granulated sugar
• ⅔ cup brown sugar (light or dark)
• ¼ tsp salt
• 1 tsp vanilla extract

🌴 Dried Fruits and Seeds

• ½ tsp coconut extract

🍹 Beverages

• 2 tbsp pineapple juice (reserved from can or fresh)

🧈 Dairy

• 14 tbsp unsalted butter (10 tbsp for batter, 4 tbsp for topping)
• ½ cup milk

🍒 Desserts

• 12 maraschino cherries (patted dry)

🍸 Beers, Wines, and Spirits

• ½ tsp rum extract (optional, for tropical depth)

👩‍🍳 Directions

Step 1: Prepare Pan & Fruit

1. Preheat oven to 350°F (175°C).
2. Grease a standard 12-cup muffin pan thoroughly with butter or non-stick spray.
3. Cut 6 pineapple rings in half. Place a half-ring in each muffin cup, forming a semicircle.
4. Press a maraschino cherry into the center of each.

Step 2: Make the Brown Sugar Topping

1. In a small bowl (or saucepan), mix 4 tbsp melted butter with ⅔ cup brown sugar.
2. Spoon about 1 tablespoon of this mixture into each muffin cup, spreading over the fruit.

Step 3: Mix Dry Ingredients

1. In a medium bowl, whisk together flour, baking powder, and salt.

Step 4: Mix Wet Ingredients

1. In a large bowl, beat 10 tbsp softened butter and ¾ cup granulated sugar until light and fluffy.
2. Add the eggs one at a time.
3. Stir in vanilla, coconut extract, pineapple juice, rum extract (if using), and lemon juice. Mix until smooth.

Step 5: Combine Wet and Dry

1. Add dry ingredients to the wet mixture in two parts, alternating with milk.
2. Mix just until combined — do not overmix.

Step 6: Fill & Bake

1. Spoon batter over the fruit mixture in each cup, filling about ¾ full.
2. Bake for 20–22 minutes, or until a toothpick comes out clean.

Step 7: Cool & Flip

1. Let cupcakes cool in the pan for 5 minutes.
2. Run a small knife around the edges to loosen.
3. Place a tray or large plate over the pan and flip quickly but carefully.
4. Tap the bottom and gently lift the pan — the cupcakes should release easily.

🍽️ Servings & Timing

• Servings: 12 cupcakes
• Prep Time: 20 minutes
• Bake Time: 22 minutes
• Cooling & Flipping Time: 10 minutes
• Total Time: ~50 minutes

These are perfect for warm-weather parties or when you want tropical vibes any time of year.

🧊 Storage & Reheating

Room Temp:

• Store in an airtight container for 1–2 days. Best enjoyed fresh.

Refrigerator:

• Refrigerate for up to 4 days. Let sit at room temp before serving or warm slightly.

Freezer:

• Freeze unfrosted, flipped cupcakes for 1 month. Wrap tightly and thaw before serving.

Reheating:

• Microwave for 10–15 seconds to revive that fresh-from-the-oven taste.

🥄 Variations

• Mini Pineapple Cupcakes: Use a mini muffin tin with diced pineapple and smaller cherries. Bake 10–12 minutes.
• Piña Colada Cupcakes: Add 1 tbsp shredded coconut to batter and top with coconut whipped cream.
• Spiced Pineapple: Add ½ tsp cinnamon or nutmeg to the batter for warmth.
• Upside-Down Banana Cupcakes: Substitute banana slices for pineapple and caramelize with brown sugar.
• Vegan Version: Use plant-based butter, dairy-free milk, and flax eggs.

❓ 10 FAQs

1. Can I use canned pineapple?
   Absolutely! It’s the easiest option. Just drain well and pat dry.
2. Why did my cupcakes stick to the pan?
   Make sure to grease the pan well, use enough brown sugar topping, and flip while warm.
3. Can I skip the rum extract?
   Yes. It adds depth but isn’t essential.
4. Can I use crushed pineapple?
   Yes, but it won’t look as pretty as the slices. It’s better for flavor than presentation.
5. Can I make these ahead of time?
   Yes — they keep well refrigerated for up to 4 days.
6. Do I need to flip them?
   You can serve them unflipped, but the presentation and texture are best when inverted.
7. What if my pineapple is too large?
   Cut rings in quarters or use tidbits for a better fit.
8. What frosting works with these?
   These are usually served without frosting, but a dollop of whipped cream or coconut frosting is delicious.
9. Can I make these gluten-free?
   Yes, use a 1:1 gluten-free flour substitute. Baking times may vary slightly.
10. Can I bake these as a cake instead?
    Yes! Use an 8-inch round cake pan and bake for 30–35 minutes.

🏁 Conclusion

These Pineapple Upside Down Cupcakes take a retro favorite and make it personal. Moist vanilla cake meets caramelized tropical fruit, and the upside-down finish creates a gorgeous, glossy topping that’s ready to impress. Each bite is rich, juicy, and bursting with sunny flavors.

Whether you’re hosting a luau, baking for a brunch, or just want to taste summer in cupcake form, this recipe is your new go-to. Easy, quick, and oh-so satisfying — what more could you want?

Adam

Pineapple Upside Down Cupcakes – Easy & Quick

There’s something magical about a dessert that flips upside down and still comes out absolutely stunning. These Pineapple Upside Down Cupcakes are the individual-sized spin on the classic cake — complete with golden caramelized pineapple, juicy maraschino cherries, and a moist vanilla coconut cupcake base. They’re everything you love about summer: tropical flavor, vibrant color, and sweet nostalgia. Best of all? They’re quick to make, easy to serve, and don’t require any fancy decorating. These cupcakes bake up tender and light, with the perfect balance of fruit and cake in every bite. From backyard BBQs to holiday dessert trays, these easy pineapple cupcakes are the kind of recipe that makes everyone think you baked all day — but you didn’t.

Print Recipe Pin Recipe

Prep Time 20 minutes mins

bake & Chill & & Flipping Time 30 minutes mins

Total Time 50 minutes mins

Servings: 12 cupcakes

Ingredients Equipment Method Notes

Ingredients

  

🍋 Fruits and Vegetables

• 6 pineapple rings halved
• 1 tsp lemon juice optional, brightens flavor

🥚 Fresh Products

• 2 large eggs

🍬 Pantry Items and Spices

• 1½ cups all-purpose flour
• 1½ tsp baking powder
• ¾ cup granulated sugar
• ⅔ cup brown sugar light or dark
• ¼ tsp salt
• 1 tsp vanilla extract

🌴 Dried Fruits and Seeds

• ½ tsp coconut extract

🍹 Beverages

• 2 tbsp pineapple juice reserved from can or fresh

🧈 Dairy

• 14 tbsp unsalted butter 10 tbsp for batter, 4 tbsp for topping
• ½ cup milk

🍒 Desserts

• 12 maraschino cherries patted dry

Equipment

• Before you start flipping cupcakes, make sure you have the following:
• 12-cup muffin pan
• Non-stick cooking spray or butter for greasing
• Mixing bowls (large and medium)
• Hand mixer or stand mixer
• Rubber spatula
• Measuring cups and spoons
• Knife and cutting board
• Small saucepan (optional for melting butter/sugar)
• Cooling rack

Method

 

Step 1: Prepare Pan & Fruit

1. Preheat oven to 350°F (175°C).
2. Grease a standard 12-cup muffin pan thoroughly with butter or non-stick spray.
3. Cut 6 pineapple rings in half. Place a half-ring in each muffin cup, forming a semicircle.
4. Press a maraschino cherry into the center of each.

Step 2: Make the Brown Sugar Topping

1. In a small bowl (or saucepan), mix 4 tbsp melted butter with ⅔ cup brown sugar.
2. Spoon about 1 tablespoon of this mixture into each muffin cup, spreading over the fruit.

Step 3: Mix Dry Ingredients

1. In a medium bowl, whisk together flour, baking powder, and salt.

Step 4: Mix Wet Ingredients

1. In a large bowl, beat 10 tbsp softened butter and ¾ cup granulated sugar until light and fluffy.
2. Add the eggs one at a time.
3. Stir in vanilla, coconut extract, pineapple juice, rum extract (if using), and lemon juice. Mix until smooth.

Step 5: Combine Wet and Dry

1. Add dry ingredients to the wet mixture in two parts, alternating with milk.
2. Mix just until combined — do not overmix.

Step 6: Fill & Bake

1. Spoon batter over the fruit mixture in each cup, filling about ¾ full.
2. Bake for 20–22 minutes, or until a toothpick comes out clean.

Step 7: Cool & Flip

1. Let cupcakes cool in the pan for 5 minutes.
2. Run a small knife around the edges to loosen.
3. Place a tray or large plate over the pan and flip quickly but carefully.
4. Tap the bottom and gently lift the pan — the cupcakes should release easily.

Notes

🧊 Storage & Reheating

Room Temp:

Store in an airtight container for 1–2 days. Best enjoyed fresh.

Refrigerator:

Refrigerate for up to 4 days. Let sit at room temp before serving or warm slightly.

Freezer:

Freeze unfrosted, flipped cupcakes for 1 month. Wrap tightly and thaw before serving.

Reheating:

Microwave for 10–15 seconds to revive that fresh-from-the-oven taste.

🥄 Variations

Mini Pineapple Cupcakes: Use a mini muffin tin with diced pineapple and smaller cherries. Bake 10–12 minutes.

Piña Colada Cupcakes: Add 1 tbsp shredded coconut to batter and top with coconut whipped cream.

Spiced Pineapple: Add ½ tsp cinnamon or nutmeg to the batter for warmth.

Upside-Down Banana Cupcakes: Substitute banana slices for pineapple and caramelize with brown sugar.

Vegan Version: Use plant-based butter, dairy-free milk, and flax eggs.

❓ 10 FAQs

Can I use canned pineapple?
Absolutely! It’s the easiest option. Just drain well and pat dry.

Why did my cupcakes stick to the pan?
Make sure to grease the pan well, use enough brown sugar topping, and flip while warm.

Can I skip the rum extract?
Yes. It adds depth but isn’t essential.

Can I use crushed pineapple?
Yes, but it won’t look as pretty as the slices. It’s better for flavor than presentation.

Can I make these ahead of time?
Yes — they keep well refrigerated for up to 4 days.

Do I need to flip them?
You can serve them unflipped, but the presentation and texture are best when inverted.

What if my pineapple is too large?
Cut rings in quarters or use tidbits for a better fit.

What frosting works with these?
These are usually served without frosting, but a dollop of whipped cream or coconut frosting is delicious.

Can I make these gluten-free?
Yes, use a 1:1 gluten-free flour substitute. Baking times may vary slightly.

Can I bake these as a cake instead?
Yes! Use an 8-inch round cake pan and bake for 30–35 minutes.

🏁 Conclusion

These Pineapple Upside Down Cupcakes take a retro favorite and make it personal. Moist vanilla cake meets caramelized tropical fruit, and the upside-down finish creates a gorgeous, glossy topping that’s ready to impress. Each bite is rich, juicy, and bursting with sunny flavors.

Whether you’re hosting a luau, baking for a brunch, or just want to taste summer in cupcake form, this recipe is your new go-to. Easy, quick, and oh-so satisfying — what more could you want?