Pineapple Upside Sugar Cookies are the kind of treat you make when you want something bright, fun, and a little nostalgic. You know those days when you want dessert to lift the mood and make the whole kitchen smell happy? That’s what these cookies do. They’re soft in the center with caramelized brown sugar on the bottom, and a juicy pop of pineapple with a tiny cherry wink on top. If you love the classic cake, you’ll adore this hand held version. I’ve made them for potlucks, kid birthdays, and even just because it’s Tuesday and the oven begs to be used.
The Story Behind This Recipe
From my kitchen to yours—Pineapple Upside Sugar Cookies mixes everyday ingredients with bright flavor. Tested, tasted, and ready for your table. Pineapple Upside Sugar Cookies are the kind of treat you make when you want something bright, fun, and a little nostalgic. You know those days when…
How to Make Pineapple Upside Down Sugar Cookies
Think of these as mini pineapple upside down cakes in cookie form, baked in a muffin pan. They’re buttery sugar cookies with that signature brown sugar pineapple base, so every bite tastes like summer. The steps are simple, and I’ll share the little tricks that keep them from sticking and help you get that perfect flip without a crumbly mess.
Start by prepping the pan. Lightly grease a standard muffin pan and, if you’ve got the patience, cut small parchment circles to fit the bottoms. This is extra, but it makes flipping a breeze. Into each cup, add a dab of softened butter and a spoon of brown sugar. Press it down gently so it coats the bottom. Then drop in a small pineapple chunk or half a ring cut to size, plus a half cherry if you like that classic look.
Now make the dough. Cream room temp butter and sugar until fluffy and pale. Mix in an egg, a splash of vanilla, and a tiny bit of almond extract if you’re feeling fancy. Whisk flour, baking powder, and salt in a separate bowl, then add it to the butter mixture. The dough will be soft but not sticky. If it’s sticky, chill it for 20 minutes. Scoop a generous tablespoon of dough and flatten it slightly in your palms. Set the dough over each pineapple cup and gently press the edges so the fruit is covered.
Bake until the edges go just golden. The tops will look like sugar cookies, but underneath is where the magic happens. Cool in the pan for about 10 minutes. To flip, run a thin knife around the edges, place a tray or cutting board over the pan, and invert in one confident motion. Lift the pan, peel off any parchment, and admire those shiny caramel bottoms with juicy fruit.
If you love the caramel fruit vibe, you might also enjoy this sweet treat detour on busy weekends: Pineapple Caramel Heaven Cake. It’s a big crowd pleaser with the same sunny flavors.
I made these for my neighbors and they vanished before dinner. One friend asked for the recipe and made them twice in a week. They’re that good, and they look adorable without any fuss.
Here’s my reassuring note: if a few stick or look rustic, they’ll still taste amazing. A little imperfection makes them feel homemade and cozy. Enjoy the first warm cookie while you plate the rest.
Shopping List
Here’s everything you need to make a batch that serves 12 to 18, depending on how generous you are with the scoops.
- Butter: Unsalted, softened. You’ll use some for the dough and a tiny bit for each muffin cup.
- Granulated sugar: For that classic sugar cookie sweetness.
- Brown sugar: Light or dark, for caramelizing under the fruit.
- Egg: Room temperature mixes in smoother.
- Vanilla extract and a hint of almond extract if you like it.
- All purpose flour: Spoon and level for accuracy.
- Baking powder and salt: A little lift and balance.
- Pineapple: Tidbits or small pieces from rings, well drained and patted dry.
- Maraschino cherries: Optional, but they add that charming look.
- Cooking spray or extra butter for greasing the pan, plus small parchment circles if you want extra insurance.
Craving more sunny cookie ideas? Try these tropical delights too: Hawaiian Pineapple Coconut Thumbprint Cookies. 
Storage & Freezing
These cookies are tender and juicy, so a little care keeps them tasting bakery fresh.
- Room temp: Store in an airtight container for 1 to 2 days. Place a sheet of parchment between layers so the caramel bottoms don’t stick.
- Refrigerator: They’ll keep 4 to 5 days. I like to microwave one for 8 to 10 seconds before eating so the caramel softens again.
- Freezer: Freeze on a tray until firm, then pack in freezer bags with parchment between cookies. They’ll last up to 2 months.
- Thawing: Let them sit at room temp or give them a short warm up in the microwave. Keep it brief to avoid over softening the fruit.
If you’re stocking your freezer for quick treats, add these cute bites to your list: Coconut Pineapple Bites. They thaw fast and satisfy tropical cravings.
Substitutions & Variations
No fresh pineapple? Canned tidbits work perfectly. Drain well and pat dry with paper towels to keep the caramel crisp and the cookie from getting soggy.
No cherries, no problem. Leave them out or swap with a tiny cube of mango. The look changes, but the flavor stays bright.
Gluten free swap. Use a good quality 1:1 baking flour. The texture stays soft and tender if the blend includes starches like tapioca or potato. For best results, let the dough rest 10 minutes to hydrate before baking.
Dairy free version. Use a vegan butter that’s made for baking. Substitute 1 tablespoon plant milk for 1 tablespoon of butter if the dough seems stiff, since some dairy free butters are firmer.
Spice it up. Stir 1 teaspoon cinnamon into the brown sugar for a warm bakery vibe. A pinch of nutmeg makes them smell like the holidays.
Super citrusy. Add 1 teaspoon lemon zest to the dough. The lemon makes the pineapple sing and adds a clean finish.
A little coconut crunch. Sprinkle sweetened shredded coconut under the dough in each muffin cup along with the brown sugar. It toasts while baking and adds texture.
Leftover pineapple ideas. If you’ve got extra fruit, try a savory twist tonight with this colorful favorite: Thai Pineapple Fried Rice. It’s quick, simple, and packed with flavor.
Pro Tips
Dry your fruit. The number one trick for pretty results is patting the pineapple dry. Too much juice will fight the caramel and can cause sticking.
Lightly pack the brown sugar. Press it gently into the muffin cups so it forms an even layer. You want a thin coat, not a thick clump, or it can bubble over.
Chill for control. If the dough feels warm or sticky, chill it for 20 minutes before scooping. Cooler dough bakes thicker and flips more cleanly.
Flip with confidence. Let the cookies rest 10 minutes after baking. Slide a thin spatula or butter knife around the edges, cover with a tray, and invert firmly. Lift slowly so any caramel stays with the cookie.
Don’t overbake. Pull them when the edges just start to color. The carryover heat finishes the centers without drying them out.
If you’re building a plate of mixed treats, these classic cousins are lovely alongside: Cherry Almond Amish Sugar Cookies. Their simplicity pairs perfectly with the fruity sparkle here.
Common Questions
Do I need a muffin pan, or can I use a sheet pan?
A muffin pan gives the best upside down effect and keeps the caramel in place. A sheet pan works only if you create small parchment lined rings to hold the sugar and fruit, which is fiddly.
Can I use pineapple rings?
Yes, just cut them into small pieces to fit the muffin cups. A full ring is too large and will cause uneven baking.
What if my cookies stick?
Let them cool 10 minutes, then run a thin knife around the edges. If a little fruit stays behind, spoon it back on. Greasing well and using parchment circles helps a lot.
How do I know they’re done?
The edges turn light golden and the tops look set. If you gently press the center, it should spring back slightly without leaving a dent.
Can I make the dough ahead of time?
Definitely. Chill the dough up to 48 hours. Scoop and press into prepared muffin cups just before baking for the freshest caramel effect.
Sweet Wrap Up for Cookie Lovers
I love how these Pineapple Upside Sugar Cookies deliver big nostalgia in a small, snackable package. You get that buttery cookie bite, the sparkle of pineapple, and a caramel finish that tastes like warm sunshine. If you’re feeling the tropical mood, keep the fun going with more pineapple bakes or even a cute thumbprint moment. For more inspiration and step by step ideas, check out this detailed guide: Pineapple Upside Down Sugar Cookies – Cookie Dough and Oven …, or this quick method I really like for busy days: Easy Pineapple Upside Down Sugar Cookies Recipe. Bake a batch, share a few, and keep one or two just for you.
Pineapple Upside Down Sugar Cookies
Ingredients
Method
- Lightly grease a standard muffin pan and cut small parchment circles for easier flipping.
- In each muffin cup, add a dab of softened butter and a spoon of brown sugar, pressing gently.
- Place a small pineapple chunk or half a ring, plus a half cherry on top in each cup.
- Cream the room temperature butter and granulated sugar until fluffy and pale.
- Mix in the egg, vanilla extract, and almond extract.
- In a separate bowl, whisk flour, baking powder, and salt, then add to the butter mixture.
- Chill the dough for 20 minutes if it feels sticky.
- Scoop a generous tablespoon of dough, flatten slightly, and place over the pineapple in each muffin cup.
- Bake until the edges are just golden, about 12-15 minutes.
- Cool in the pan for about 10 minutes before flipping.
- Run a thin knife around the edges, invert a tray over the pan, and carefully flip.
