12 Delicious Pineapple Upside Down Cupcakes Recipes

Let’s turn the classic pineapple upside-down cake into bite-sized delights with these 12 irresistible cupcake recipes! Perfect for home cooks looking to add a tropical twist to their baking repertoire, these cupcakes promise a sweet, caramelized topping and moist cake in every bite. Whether you’re prepping for a party or just craving something sweet, dive into our roundup and discover your next favorite treat!

Classic Pineapple Upside Down Cupcakes

Alright, let’s dive into the whimsical world of baking with a twist—literally! These Classic Pineapple Upside Down Cupcakes are like little pockets of sunshine, perfect for when you want to flip your day around (see what I did there?).

Ingredients

• 1 cup all-purpose flour (because, let’s face it, it’s the MVP of baking)
• 1/2 cup unsalted butter, softened (room temp is your friend here)
• 3/4 cup granulated sugar (for that sweet, sweet happiness)
• 2 large eggs (preferably room temp, they mix better)
• 1 tsp vanilla extract (the good stuff, none of that imitation nonsense)
• 1/2 cup milk (whole milk makes it richer, but any will do)
• 1 tsp baking powder (the unsung hero of fluffiness)
• 1/4 tsp salt (just a pinch to balance the sweetness)
• 6 pineapple rings (canned is fine, but fresh is a game-changer)
• 6 maraschino cherries (because what’s a pineapple upside-down without these little gems?)
• 1/4 cup brown sugar (for that caramelized magic)
• 2 tbsp melted butter (extra love for the topping)

Instructions

1. Preheat your oven to 350°F (175°C). Trust me, starting with a hot oven is non-negotiable.
2. In a bowl, cream together the softened butter and granulated sugar until light and fluffy. This is where your arm workout pays off.
3. Beat in the eggs one at a time, then stir in the vanilla. Pro tip: Crack eggs on a flat surface to avoid shell shrapnel.
4. Combine the flour, baking powder, and salt in another bowl. Gradually add to the wet ingredients, alternating with milk. Mix just until combined—overmixing is the enemy of tender cupcakes.
5. In a small bowl, mix the melted butter and brown sugar. Spoon this into the bottom of each cupcake liner, then place a pineapple ring and cherry on top.
6. Divide the batter evenly among the liners, filling each about 2/3 full. Bake for 20-25 minutes, or until a toothpick comes out clean. The smell will drive you crazy—resist the urge to peek!
7. Let cool in the pan for 5 minutes, then flip onto a wire rack. The grand reveal is the best part—watch those golden tops glisten.

Just imagine biting into these moist, caramel-kissed cupcakes with bursts of pineapple and cherry. Serve them warm with a dollop of whipped cream, or go rogue and pair with a scoop of coconut ice cream for a tropical twist.

Cherry Pineapple Upside Down Cupcakes

Buckle up, buttercups, because we’re about to turn your cupcake game upside down—literally! These Cherry Pineapple Upside Down Cupcakes are the perfect mashup of retro charm and modern convenience, packed with juicy cherries and tangy pineapple that’ll make your taste buds do a happy dance.

Ingredients

• 1 cup all-purpose flour (because greatness starts with a solid foundation)
• 1/2 cup unsalted butter, softened (room temp is key for that smooth, dreamy texture)
• 3/4 cup granulated sugar (for that sweet, sweet love)
• 2 large eggs (room temp, unless you enjoy the thrill of lumpy batter)
• 1 tsp vanilla extract (the secret handshake of baking)
• 1/2 cup crushed pineapple, drained (squeeze out the drama, keep the flavor)
• 1/2 cup maraschino cherries, halved (because whole cherries are just showing off)
• 1/4 cup brown sugar (for that caramelized hug at the bottom)
• 1 tbsp pineapple juice (leftover from the crushed pineapple—waste not, want not)

Instructions

1. Preheat your oven to 350°F (175°C)—no guessing games here, precision is your friend.
2. Line a muffin tin with cupcake liners and lightly spray with non-stick spray—trust me, it’s worth the extra step.
3. In a small bowl, mix brown sugar and pineapple juice, then divide evenly among the cupcake liners.
4. Arrange cherry halves cut-side down over the sugar mixture in each liner—this is where the magic (and the upside-down part) happens.
5. In a medium bowl, cream together butter and granulated sugar until light and fluffy—about 3 minutes. Patience pays off here.
6. Beat in eggs one at a time, then stir in vanilla extract—this is where your batter starts to sing.
7. Gradually mix in flour until just combined—overmixing is the enemy of fluffy cupcakes.
8. Fold in crushed pineapple gently—think of it as a delicate dance, not a mosh pit.
9. Spoon batter over the cherries in the liners, filling each about 3/4 full—no overzealous pouring, please.
10. Bake for 20-25 minutes, or until a toothpick comes out clean—because nobody likes a guesser.
11. Let cool in the pan for 5 minutes, then transfer to a wire rack to cool completely—resisting the urge to flip them early is a test of willpower.

After the final step, wrap up with 2–3 natural sentences about the texture, flavor, or a creative way to serve it — no generic conclusions. The first word of your introduction must begin with the letter ‘A’.

Absolutely irresistible, these cupcakes boast a moist, tender crumb with a caramelized fruit topping that’s sticky, sweet, and slightly tangy. Serve them warm with a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent treat that’ll have everyone asking for seconds.

Coconut Pineapple Upside Down Cupcakes

Get ready to flip your world upside down with these tropical treats that’ll have you dreaming of beachside picnics and sun-soaked afternoons. These cupcakes are a playful twist on the classic, blending the creamy dreaminess of coconut with the zesty zing of pineapple for a bite that’s as fun to make as it is to devour.

Ingredients

• 1 cup all-purpose flour (because even cupcakes need a good foundation)
• 1/2 cup unsalted butter, softened (room temp is key for that perfect mix)
• 3/4 cup granulated sugar (for that sweet, sweet love)
• 2 large eggs (preferably room temp, they mix in smoother)
• 1/2 cup coconut milk (the secret to tropical moisture)
• 1 tsp vanilla extract (the vanilla bean’s gift to bakers)
• 1/2 cup crushed pineapple, drained (squeeze out the extra juice for the perfect texture)
• 1/4 cup shredded coconut (for that extra crunch and flair)
• 6 pineapple rings (because presentation is everything)
• 6 maraschino cherries (the classic upside-down cake jewel)

Instructions

1. Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners. Tip: Even if you’re using liners, a light spray of cooking oil ensures they peel off perfectly.
2. In a large bowl, cream together the softened butter and sugar until light and fluffy. This is where the magic starts, so don’t rush it.
3. Beat in the eggs one at a time, then stir in the vanilla extract. Tip: Adding eggs one by one ensures a smoother batter.
4. Alternately add the flour and coconut milk to the batter, starting and ending with the flour. Mix until just combined. Overmixing is the enemy of fluffy cupcakes.
5. Fold in the crushed pineapple and shredded coconut. This is where the tropical vibes kick in.
6. Place a pineapple ring at the bottom of each cupcake liner, and top with a cherry in the center. Tip: Pat the pineapple rings dry to prevent a soggy bottom.
7. Divide the batter evenly among the cupcake liners, filling each about 3/4 full.
8. Bake for 20-25 minutes, or until a toothpick inserted into the center comes out clean. The tops should be golden and springy to the touch.
9. Let cool in the pan for 5 minutes, then transfer to a wire rack to cool completely. Tip: Flipping them while slightly warm ensures the pineapple topping stays put.

Absolutely irresistible, these cupcakes boast a moist, fluffy crumb with a caramelized pineapple top that’s sticky, sweet, and slightly tangy. Serve them at your next brunch for a guaranteed conversation starter, or keep them all to yourself—we won’t judge.

Rum Glazed Pineapple Upside Down Cupcakes

Yummy doesn’t even begin to cover it—these Rum Glazed Pineapple Upside Down Cupcakes are like a tropical vacation in every bite, minus the sunburn and questionable tan lines. Perfect for when you want to impress but also keep things delightfully easy.

Ingredients

• 1 cup all-purpose flour (because greatness starts with the basics)
• 1/2 cup unsalted butter, softened (I swear by room temp butter for that perfect mix)
• 3/4 cup brown sugar (for that deep, caramel-like sweetness)
• 2 large eggs (room temp, unless you enjoy the suspense of lumpy batter)
• 1 tsp vanilla extract (the good stuff, please)
• 1/2 cup crushed pineapple, drained (save the juice for a cheeky sip)
• 1/4 cup rum (because why not add a little fun to your cupcakes?)
• Maraschino cherries, for topping (the more, the merrier, I say)

Instructions

1. Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners. Tip: A happy oven makes happy cupcakes.
2. In a bowl, cream together the butter and brown sugar until light and fluffy. This is where the magic starts.
3. Beat in the eggs one at a time, then stir in the vanilla. Patience is key—don’t rush the eggs.
4. Gradually mix in the flour until just combined. Overmixing is the enemy of fluffy cupcakes.
5. Fold in the crushed pineapple. This is where the tropical vibes kick in.
6. Divide the batter evenly among the cupcake liners. A cookie scoop is your best friend here.
7. Bake for 20-25 minutes, or until a toothpick comes out clean. Tip: Rotate the pan halfway for even baking.
8. While still warm, brush the tops with rum. This step is non-negotiable for that boozy glaze.
9. Top each cupcake with a maraschino cherry. Go ahead, make it pretty.

Moist, fluffy, and with just the right amount of rum kick, these cupcakes are a showstopper. Serve them at your next brunch and watch them disappear faster than your resolve to diet.

Brown Sugar Pineapple Upside Down Cupcakes

Delightfully devilish and dripping with caramelized charm, these cupcakes are your ticket to tropical bliss without the airfare. Imagine biting into a fluffy cloud, only to discover it’s been partying with pineapple and brown sugar all night—now that’s a dessert with stories to tell.

Ingredients

• 1 cup all-purpose flour (because greatness starts with the basics)
• 1/2 cup brown sugar, packed (the secret to that deep, molasses kiss)
• 1/4 cup unsalted butter, melted (I like mine with a golden tan, not a sunburn)
• 1/2 cup crushed pineapple, drained (keep the juice for a cheeky sip)
• 1 large egg, room temp (it’s all about that even bake, baby)
• 1 tsp vanilla extract (the more, the merrier, I always say)
• 1/2 tsp baking powder (the unsung hero of lift and lightness)
• Pinch of salt (to make the sweet stuff sing)

Instructions

1. Preheat your oven to 350°F (175°C)—no guessing, just precision.
2. Line a muffin tin with cupcake liners, because nobody likes a sticky situation.
3. In a bowl, mix the melted butter and brown sugar until they’re best friends.
4. Add the egg and vanilla extract to the party, whisking until smooth.
5. Sift in the flour, baking powder, and salt, stirring just until combined—overmixing is the enemy of fluff.
6. Fold in the crushed pineapple with a gentle hand; think of it as tucking in a baby, not squashing a bug.
7. Divide the batter evenly among the liners, filling each about 2/3 full.
8. Bake for 20-25 minutes, or until a toothpick comes out clean—trust the process, not the clock.
9. Let them cool in the tin for 5 minutes, then transfer to a wire rack. Patience is a virtue, especially with upside-down cakes.

Velvety soft with pockets of juicy pineapple and a caramelized top that crackles with every bite, these cupcakes are a mini vacation in every bite. Serve them warm with a dollop of whipped cream or a scoop of vanilla ice cream for that ‘I meant to share’ lie we all tell ourselves.

Caramel Pineapple Upside Down Cupcakes

Get ready to flip your world upside down with these Caramel Pineapple Upside Down Cupcakes! They’re the perfect blend of sweet, tangy, and downright delicious, guaranteed to make your taste buds do a happy dance.

Ingredients

• 1 cup all-purpose flour (because greatness starts with the basics)
• 1/2 cup unsalted butter, softened (I swear by room temp butter for that perfect creaminess)
• 3/4 cup granulated sugar (for that sweet, sweet love)
• 2 large eggs (room temp, please, for a smoother batter)
• 1 tsp vanilla extract (the good stuff, none of that imitation nonsense)
• 1/2 cup pineapple juice (reserved from the rings, waste not!)
• 6 pineapple rings (the star of the show, make ’em fresh if you can)
• 1/2 cup brown sugar (for that deep, caramel magic)
• Maraschino cherries (because what’s a pineapple upside down without these little red gems?)

Instructions

1. Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners. Tip: A light spray of cooking oil on the liners prevents sticking.
2. In a bowl, cream together the softened butter and granulated sugar until fluffy. This is where the magic starts, so don’t rush it.
3. Beat in the eggs one at a time, then stir in the vanilla extract. Tip: Adding eggs one by one ensures a smoother batter.
4. Alternately add the flour and pineapple juice to the batter, starting and ending with flour. Mix until just combined. Overmixing is the enemy of fluffy cupcakes.
5. Place a pineapple ring at the bottom of each liner, add a cherry in the center, and sprinkle with brown sugar. This creates the caramel layer that’ll make your cupcakes unforgettable.
6. Divide the batter evenly among the liners, covering the pineapple layer. Tip: A cookie scoop makes this step a breeze and keeps things tidy.
7. Bake for 20-25 minutes, or until a toothpick inserted comes out clean. The tops should be golden and springy to the touch.
8. Let cool for 5 minutes, then invert onto a serving plate. Do this while still warm for the perfect release.

These cupcakes are a tropical paradise in every bite, with the caramelized pineapple and cherry creating a moist, flavorful masterpiece. Try serving them warm with a scoop of vanilla ice cream for an extra indulgent treat.

Spiced Pineapple Upside Down Cupcakes

Unbelievably, these Spiced Pineapple Upside Down Cupcakes are here to turn your dessert game upside down—literally! Packed with tropical vibes and a kick of spice, they’re the perfect little cakes to brighten up any day, rain or shine.

Ingredients

• 1 cup all-purpose flour (because sometimes, simple is spectacular)
• 1/2 cup unsalted butter, melted (I swear by the rich flavor it adds)
• 3/4 cup brown sugar (for that deep, caramel-like sweetness)
• 1 tsp vanilla extract (the good stuff, please)
• 2 eggs, room temperature (they mix in smoother, trust me)
• 1/2 cup crushed pineapple, drained (save the juice for a cheeky sip)
• 1 tsp cinnamon (for a warm, spicy hug in every bite)
• 1/2 tsp nutmeg (a little goes a long way)
• Maraschino cherries (because what’s a pineapple upside-down without these little red gems?)

Instructions

1. Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners. Tip: A light spray of cooking oil on the liners ensures your cupcakes pop out easily.
2. In a bowl, mix the melted butter and brown sugar until well combined. This is your golden ticket to flavor town.
3. Add the vanilla extract and eggs to the butter mixture, beating until smooth. Room temp eggs blend better, preventing a lumpy batter.
4. Gently fold in the flour, cinnamon, and nutmeg. Overmixing is the enemy of fluffy cupcakes—stop when just combined.
5. Place a cherry in the bottom of each liner, then spoon a teaspoon of crushed pineapple over it. This creates the ‘upside-down’ magic.
6. Divide the batter evenly among the liners, filling each about 2/3 full. They’ll rise, so don’t go overboard.
7. Bake for 20-25 minutes, or until a toothpick comes out clean. Tip: The tops should be golden and spring back when lightly touched.
8. Let cool in the tin for 5 minutes, then transfer to a wire rack. Flipping them while warm ensures the pineapple layer stays intact.

Moist, fluffy, and with a caramelized pineapple top, these cupcakes are a tropical escape in every bite. Serve them warm with a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent treat.

Vegan Pineapple Upside Down Cupcakes

Who knew that flipping things upside down could lead to such deliciousness? These Vegan Pineapple Upside Down Cupcakes are here to turn your dessert game on its head, literally, with a tropical twist that’ll have you doing a happy dance. Perfect for when you want to impress without the stress, these little gems are as fun to make as they are to eat.

Ingredients

• 1 1/2 cups all-purpose flour (because even cupcakes need a solid foundation)
• 1 cup granulated sugar (the sweet talker of the bunch)
• 1 tsp baking soda (the lifter of spirits and cakes)
• 1/2 tsp salt (to balance the sweet, like a good friend)
• 1/3 cup vegetable oil (extra virgin olive oil is my go-to, but any neutral oil works)
• 1 tbsp apple cider vinegar (for that tangy kick)
• 1 tsp vanilla extract (the essence of happiness)
• 1 cup pineapple juice (straight from the can, no cheating)
• 6 pineapple rings (because we’re fancy like that)
• 6 maraschino cherries (the jewel on top)
• 2 tbsp brown sugar (for that caramelized magic)

Instructions

1. Preheat your oven to 350°F (175°C). Let’s get this party started.
2. In a large bowl, whisk together the flour, granulated sugar, baking soda, and salt. No lumps allowed—we’re smooth operators here.
3. Add the vegetable oil, apple cider vinegar, vanilla extract, and pineapple juice to the dry ingredients. Mix until just combined. Tip: Overmixing is the enemy of fluffy cupcakes.
4. Place a pineapple ring and a cherry in the bottom of each cupcake liner. Sprinkle with brown sugar. This is where the magic happens.
5. Pour the batter over the pineapple and cherry, filling each liner about 3/4 full. They’ll rise, so don’t go overboard.
6. Bake for 20-25 minutes, or until a toothpick comes out clean. Tip: Ovens can be sneaky, so keep an eye on them after 20 minutes.
7. Let cool for 5 minutes, then flip onto a serving plate. Tip: Patience is key here—waiting ensures your cupcakes don’t fall apart.

Unbelievably moist with a caramelized pineapple top that’s to die for, these cupcakes are a tropical vacation in every bite. Serve them warm with a dollop of coconut whipped cream for an extra indulgent treat that’ll have everyone asking for seconds.

Gluten-Free Pineapple Upside Down Cupcakes

Kickstart your baking adventure with these gluten-free pineapple upside-down cupcakes that are as fun to make as they are to devour. Perfect for those who love a tropical twist without the gluten guilt, these little gems are sure to brighten any dessert table.

Ingredients

• 1 cup gluten-free flour blend (I swear by Bob’s Red Mill for that perfect crumb)
• 1/2 cup unsalted butter, melted (because everything’s better with butter, right?)
• 3/4 cup brown sugar (pack it like you mean it)
• 2 large eggs, room temp (they mix in smoother, trust me)
• 1 tsp vanilla extract (the good stuff, none of that imitation nonsense)
• 1/2 cup crushed pineapple, drained (save the juice for a cheeky sip)
• Maraschino cherries, for topping (the more, the merrier)

Instructions

1. Preheat your oven to 350°F and line a muffin tin with cupcake liners. No one likes a sticky situation.
2. In a bowl, mix the melted butter and brown sugar until it’s as smooth as your favorite jazz playlist.
3. Beat in the eggs one at a time, then stir in the vanilla. This is where the magic starts.
4. Gently fold in the gluten-free flour blend until just combined. Overmixing is the enemy of fluffy cupcakes.
5. Spoon the batter into the liners, filling each about halfway. Patience is key here.
6. Top each with a spoonful of crushed pineapple and a cherry. It’s like putting a hat on a snowman.
7. Bake for 20-25 minutes, or until a toothpick comes out clean. Watch them like a hawk in the last 5 minutes.
8. Let them cool in the tin for 5 minutes, then transfer to a wire rack. They need their space.

Absolutely divine when served warm, these cupcakes boast a moist texture with a caramelized pineapple top that’s to die for. Try serving them with a dollop of coconut whipped cream for an extra tropical punch.

Mini Pineapple Upside Down Cupcakes

Mmm, who can resist the sweet, tropical charm of pineapple upside-down cake? Now, imagine all that gooey, caramelized goodness in a bite-sized cupcake form. Perfect for when you want to impress at potlucks or just treat yourself to a mini vacation in every bite.

Ingredients

• 1 cup all-purpose flour (because, let’s face it, we’re not making this gluten-free)
• 1/2 cup granulated sugar (the sweet stuff that makes life worth living)
• 1/4 cup unsalted butter, melted (I like to pretend this makes it healthier)
• 1 large egg, room temp (because nobody likes a cold egg in their batter)
• 1/2 cup pineapple juice (reserved from the tidbits, because waste not, want not)
• 1/2 cup pineapple tidbits (the star of the show, obviously)
• 1/4 cup maraschino cherries, halved (for that classic look and a pop of color)
• 1/4 cup brown sugar (for that caramelized magic on top)
• 1 tbsp butter, melted (extra butter because why not?)

Instructions

1. Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners. This is not the time to skip the liners unless you enjoy scrubbing pans.
2. In a small bowl, mix the brown sugar and 1 tbsp melted butter. Spoon this mixture into the bottom of each cupcake liner—about a teaspoon each. This is the secret to that irresistible caramel topping.
3. Place a cherry half in the center of each liner, then surround it with pineapple tidbits. Arrange them like you’re decorating a tiny edible throne.
4. In a larger bowl, whisk together the flour and granulated sugar. Add the 1/4 cup melted butter, egg, and pineapple juice, stirring until just combined. Overmixing is the enemy of fluffy cupcakes.
5. Divide the batter evenly among the prepared liners, filling each about 2/3 full. They’ll rise, so don’t get greedy.
6. Bake for 18-20 minutes, or until a toothpick inserted into the center comes out clean. The tops should be golden and spring back when lightly touched.
7. Let the cupcakes cool in the pan for 5 minutes, then transfer to a wire rack. Waiting is the hardest part, but it’s worth it to avoid a caramel burn.

Unbelievably moist with a sticky-sweet top and a tender crumb, these mini delights are like sunshine on a plate. Serve them warm with a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent treat.

Chocolate Drizzled Pineapple Upside Down Cupcakes

Ready to flip your world upside down with a dessert that’s as fun to make as it is to eat? These Chocolate Drizzled Pineapple Upside Down Cupcakes are a whimsical twist on the classic, combining the tropical vibes of pineapple with the indulgent touch of chocolate—because why choose when you can have both?

Ingredients

• 1 cup all-purpose flour (because even cupcakes need a solid foundation)
• 1/2 cup unsalted butter, softened (room temp is key for that perfect creaminess)
• 3/4 cup granulated sugar (for that sweet, sweet happiness)
• 2 large eggs (preferably room temp, they mix better that way)
• 1 tsp vanilla extract (the secret whisper of flavor)
• 1/2 cup crushed pineapple, drained (squeeze out the excess juice for the perfect texture)
• 1/4 cup brown sugar (for that caramelized magic on top)
• Maraschino cherries (the classic crown jewel of any upside-down cake)
• 1/2 cup melted chocolate chips (because everything’s better with chocolate)

Instructions

1. Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners. This is where the magic begins.
2. In a bowl, cream together the softened butter and granulated sugar until light and fluffy. Tip: This is your arm workout for the day—embrace it.
3. Beat in the eggs one at a time, then stir in the vanilla extract. Patience is key; add them slowly for a smooth batter.
4. Gradually mix in the flour until just combined. Overmixing is the enemy of fluffy cupcakes.
5. Place a teaspoon of brown sugar at the bottom of each cupcake liner, followed by a pineapple chunk and a cherry. This is your upside-down masterpiece in the making.
6. Spoon the batter over the pineapple and cherries, filling each liner about 2/3 full. They need room to rise and shine.
7. Bake for 20-25 minutes, or until a toothpick comes out clean. The smell will be your first clue they’re done.
8. Let them cool for 5 minutes in the tin, then flip onto a wire rack. The big reveal should be met with oohs and aahs.
9. Drizzle with melted chocolate while still slightly warm. The chocolate will set but stay gloriously gooey.

Delight in the contrast of the caramelized pineapple against the moist cake, with the chocolate adding a decadent finish. Serve these beauties at your next brunch or as a bold statement dessert—because ordinary cupcakes are so last season.

Bourbon Infused Pineapple Upside Down Cupcakes

Ever find yourself staring at a pineapple and thinking, ‘You’re sweet, but you could use a little kick’? Well, buckle up, because we’re about to take that tropical vibe and give it a bourbon-infused makeover that’ll have your taste buds doing the cha-cha.

Ingredients

• 1 cup all-purpose flour (because greatness starts with a solid foundation)
• 1/2 cup unsalted butter, softened (I like to pretend it’s sunshine in stick form)
• 3/4 cup brown sugar (for that deep, caramel hug)
• 2 large eggs, room temp (they mix better when they’re not shivering)
• 1/4 cup bourbon (the smoother, the better—your cupcakes deserve the good stuff)
• 1 tsp vanilla extract (the secret handshake of baking)
• 1/2 cup diced pineapple (fresh is fab, but canned works in a pinch)
• Maraschino cherries, for topping (because every cupcake deserves a cherry on top)

Instructions

1. Preheat your oven to 350°F (175°C). This is where the magic starts, so no rushing!
2. In a bowl, cream together the butter and brown sugar until it’s lighter than your mood on a Friday. Tip: Scrape the bowl sides to ensure everything’s mingling nicely.
3. Beat in the eggs one at a time, then welcome the vanilla and bourbon to the party. Tip: Pour the bourbon slowly unless you’re aiming for tipsy cupcakes.
4. Gently fold in the flour until just combined. Overmixing is the enemy of fluffy cupcakes!
5. Divide the diced pineapple among cupcake liners, then spoon the batter over the top. They’re like little treasure chests waiting to be discovered.
6. Bake for 20-25 minutes, or until a toothpick comes out clean. Tip: Rotate the pan halfway for even baking—no favoritism here.
7. Let them cool for a hot minute, then flip each cupcake onto a plate. Crown with a cherry and serve with flair.

Fluffy, moist, and with a bourbon kick that whispers rather than shouts, these cupcakes are a dessert rebellion. Serve them at your next brunch and watch as they steal the spotlight, no audition needed.

Conclusion

Baking these 12 Delicious Pineapple Upside Down Cupcakes Recipes promises a sweet adventure in your kitchen! Each recipe offers a unique twist on the classic, ensuring there’s something for every taste. We’d love to hear which one becomes your favorite—drop us a comment below. Loved this roundup? Share the pineapple love by pinning this article on Pinterest for fellow bakers to discover!