Pineapple Upside Down Cookies are my go-to when I want something a little extra without a ton of effort. Ever get hit with a craving for sweet, fruity, gooey goodness but can’t be bothered to fight with a cake pan? Me too. That’s why I made a batch of these last weekend, wishing I’d discovered them sooner. For anyone who likes easy bakes and tropical flavor (and who doesn’t, right?), or folks who just want a change from classic chocolate chip, let’s dive in. If you’re into fun cookies, check out these delicious pumpkin cookies with cream cheese frosting or my favorite jack-o-lantern chocolate cookies to bake too.
How to Make Pineapple Upside Down Sugar Cookies
Alright, let’s not overcomplicate this. The best part about Pineapple Upside Down Cookies? They might look kinda fancy but the steps are easy—even if you’ve got a messy kitchen like mine. All you need is a soft sugar cookie base, a few slices of canned pineapple, and those bright red maraschino cherries (the more the merrier, honestly).
First, you’ll whip up your favorite sugar cookie dough. You can totally use store-bought if you’re rushed. I’ve tried it—no one complained! Next, you’ll grab a muffin tin, spray it well (trust me here, nothing sticks like caramelized sugar) and sprinkle a little brown sugar in the bottom of each cup. Put a pineapple chunk and a cherry on top of that sugar.
Spoon the dough over your fruit and squish it down just a bit—don’t worry if it looks messy. Bake until the edges get golden, then let ‘em cool a tick longer than you think. The hardest part? Flipping them out without “breaking” the cookies. I botched a couple the first time, but the smell kept me patient. If you love pineapple desserts in general, you might enjoy my deliciously easy pineapple heaven cake recipe.
“I made these for a backyard BBQ and everyone thought they’d come from a bakery. Honest, they’re that pretty fresh out of the oven!”
Shopping List
So before you get started, double-check your pantry. Maybe this is nitpicky, but I always forget something and have to go knocking on my neighbor’s door. Here’s what you’ll need for Pineapple Upside Down Cookies:
- One can of pineapple slices or tidbits.
- Jar of maraschino cherries.
- Brown sugar (don’t skimp, it’s magic here).
- Sugar cookie dough, homemade or store-bought.
- Butter (just a little).
That’s it. If you’re doing this for a crowd, go ahead and buy two cans of pineapple. No regrets, believe me. Now, every ingredient is easy to spot at most stores, even the tiny ones near me.
“My kids asked for these two weekends in a row! Way easier than juggling a big sheet cake, and less cleanup by far.”
Storage & Freezing
Here’s a legit dilemma: you made a whole tray, now what? Pineapple Upside Down Cookies will stay soft and tasty for a couple days at room temp. After that, the fruit will make them a bit sticky, so pop them in an airtight container if you don’t eat them fast. Sometimes I stash a batch in the fridge, especially in summer. It keeps them fresher, and they taste amazing cold.
If you’re thinking ahead (I salute you), these cookies actually freeze well. Let them cool completely first. I put parchment between layers and use a freezer bag. Grab one straight from the freezer and let it sit for a few—you’ve got a snack ready whenever. Reheating? Just 10 seconds in the microwave brings the gooeyness back.
“The freezing tip saved a batch when my family forgot about them. Still tasted bakery-fresh after a week!”
Substitutions & Variations
Not everyone’s into maraschino cherries—my sister, for one, always picks hers out. No sweat, just leave them off or sub slivers of strawberry. Want something more indulgent? Swap brown sugar for caramel syrup under the pineapple. For a lighter bite, try fresh pineapple (though I admit, canned is less work after a long day).
Different cookie doughs work too. Sugar is classic, but I’ve seen people use shortbread or even snickerdoodle. Gluten free flour blends also do fine. Honestly, there’s room for experimentation here—whatever you have on hand will probably be delicious, just gotta keep that buttery-sweet-tangy thing going.
Pro Tips
- Spray your muffin pan—seriously, lots.
- Use pineapple tidbits if you’re not patient enough to slice rings.
- Let cookies cool in pan at least 10 minutes to avoid messy breakups.
- For sparkle, sprinkle a tad more brown sugar on top pre-bake.
It’s no five-star restaurant dessert, but these Pineapple Upside Down Cookies will impress every cookie monster you know.
Common Questions
Q: Can I use fresh pineapple instead of canned?
A: Yup, just chop it into bite-size pieces. Canned is a bit sweeter, but both work.
Q: What if I don’t have a muffin tin?
A: Make them “free-form” on a baking sheet—they’ll be less perfect, but still yummy.
Q: Do I need to drain the pineapple?
A: Briefly pat it dry with paper towels, so you don’t get soggy cookies.
Q: Can I skip cherries?
A: Of course! They’re not a must.
Q: How long do leftovers last?
A: Usually two or three days sealed up. After that, freeze them for later.
Ready to Bake? Here’s My Last Word
All things considered, these Pineapple Upside Down Cookies are a breeze—no fussy steps and a crowd-pleaser that’ll make you look like you’ve got your life together. Plus, you can always adapt the idea if you’re feeling creative. If you loved this, try peeking at this Pineapple Upside Down Sugar Cookies – Cookie Dough and Oven … for a totally different spin, or check out Easy Pineapple Upside Down Sugar Cookies Recipe for even more ways to tweak and perfect the treat. Trust me, your kitchen will smell like a dream, and folks will be asking for the recipe on repeat. Let me know how yours turn out!
Pineapple Upside Down Sugar Cookies
Ingredients
Method
- Preheat the oven to 350°F (175°C).
- Spray a muffin tin well to prevent sticking.
- Sprinkle a little brown sugar in the bottom of each muffin cup.
- Place a pineapple chunk and a cherry on top of the brown sugar in each cup.
- Spoon the sugar cookie dough over the fruit and squish it down slightly.
- Bake the cookies in the preheated oven until the edges are golden, about 15 minutes.
- Let the cookies cool in the pan for at least 10 minutes before attempting to flip them out.
