Tantalizing Pineapple Upside Down Cupcakes You’ll Love to Bake!

Pineapple Upside Down Cupcakes are an absolute lifesaver whenever you’re craving something sweet and sunny but don’t want to make a giant cake. Tiny cakes that pack a punch, honestly. If your house is anything like mine, desserts vanish in a blink, so small batch is just smart. Plus, less mess. These little beauties have that gooey caramelized pineapple top (which is technically the bottom, but who’s arguing). And if you want even more fruity inspiration, check out this dessert cousin: apple cider cupcakes with brown sugar cinnamon buttercream. Alright, let’s dive into why these cupcakes need to get in your oven ASAP.

Why You’ll Love This Recipe

Well, first off, they look adorable. Honestly, can you picture showing up to a party with a tray of these? Queue people hovering. But that’s not all. The cupcakes are soft and fluffy, but the real win is that sweet, sticky glaze on top thanks to the brown sugar and pineapple juice. Kiddos and grownups both go wild for them at my place. Plus…they’re way easier than they look. Cake mix works too, in a pinch. I love recipes that trick folks into thinking you’re a five-star pastry chef even when you’re kinda just throwing stuff together between laundry loads. And oh—there’s something about biting into a maraschino cherry that’s just fun.

Ingredient Notes and Shopping Tips

Let’s talk groceries before you run out the door. For these Pineapple Upside Down Cupcakes, you’ll definitely need canned pineapple rings and maraschino cherries—don’t skip ’em. Grab light brown sugar, some plain white granulated sugar (nothing fancy here), basic flour, and eggs. If you want to jazz it up, feel free to swap in pineapple tidbits or fresh pineapple for an extra-tangy taste, though honestly the canned stuff caramelizes just right. Oh! Don’t forget the unsalted butter, because salted here gets a bit weird (trust me). If you’re feeling wild, toss in a bit of vanilla or cinnamon—my cousin swears by it. Real talk: cupcakes turn out just as good even if you “measure” butter with your eyes. Not that I’ve done that…often.

How to Make Pineapple Upside-Down Cupcakes

Alright, let’s get our hands a little sticky (and your kitchen will smell so good). First, you melt that butter, mix it with brown sugar, and spoon just a smidge into each cupcake cup. Then you press a pineapple slice into the sugar (sometimes I have to trim them with scissors to make ’em fit), and a cherry right in the middle—just plop it there. Pour the cake batter over the top, not too full or you’ll be scraping cupcake goo off your oven floor (been there). Bake until puffed and golden. Now this next part gets tricky—wait about 5 minutes, then flip ’em out onto a rack. If you wait too long, you’ll be taking a chisel to your pan. And try to resist eating them while still hot (good luck).

Leftovers

If you’re lucky enough to have any leftovers, pop ‘em in the fridge. Trust me, they actually taste kinda dreamy cold, but you can warm one for like 10 seconds in the microwave if you want the gooey vibes back. I toss leftovers in a covered glass container—they’ll keep three days easy. Sometimes I freeze extras, but honestly, they’re never here that long.

Krystle’s Tips

Nobody tells you this, but…

• Use cupcake liners if your pan loves to stick, but cooking spray is your best friend.
• Keep those cupcake holes about two-thirds full (overflow is real, folks).
• For a tropical twist, swap cherries for blueberries or even a chunk of mango.
• If you want a fun side, make this pineapple cucumber salad for a super fresh summer plate.
  My favorite tip? Sneak a little extra brown sugar underneath the pineapple for extra sticky flavor bombs. Just trust me.

Common Questions

Can I use fresh pineapple instead of canned?
Yep! Just slice it thin so it caramelizes, and cut pieces to fit your pan. Canned is easier, but do you.

Should these be served warm or cold?
Whatever you like. Warm means gooey and melty, cold means firm and sweet. I’ve been known to eat both from the fridge at midnight.

What’s the best way to flip them out without making a mess?
Run a butter knife around the edge, put a pan or tray over the muffin tin, and flip fast. Pray for pineapple gravity.

Can I use cake mix for the batter?
Absolutely! Yellow cake mix is classic. You’ll just skip a few steps.

Can I double the recipe?
Totally. Just space them out on your racks so the heat gets even, and wait between batches if your oven’s tiny.

Sweet Treats, Just Like Home

There you have it! These little Pineapple Upside Down Cupcakes are basically a party trick in dessert form. You get all the pineapple sunshine and sticky, golden brown sugar topping that’s usually saved for huge cakes. Don’t be surprised if these are gone before they’ve even cooled. Need more cupcake goodness? Check out Pineapple Upside Down Cupcakes | The Girl Who Ate Everything and for a stepwise walk-through, there’s Pineapple Upside-Down Cupcakes – Sugar Spun Run. If you end up with extra pineapple, you might also love my favorite easy pineapple juice cake recipe for next time. Anyway, don’t stress the details—just bake, eat, and enjoy. You’re gonna love these!

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