
Check out these cheery Christmas Pineapple Upside-Down Sugar Cookies—they mash up two old-school desserts in one! I'm wild about the mix of sweet sugar cookie and gooey caramelized pineapple plus the fun pop of cherry. They're a playful surprise for your Christmas treat tray.
Irresistible Holiday Classic
The cool part about these cookies? They're like mini pineapple upside-down cakes in bite-sized form. They're a breeze to throw together and totally eye-catching with those colorful chunks of pineapple and red cherries. Trust me, everyone from the young crowd to the grown-ups will reach for these.
Stuff to Grab
- For the Sweet Top Layer: - Juicy maraschino cherries - Pineapple (drain it well) - Brown sugar for the gooey touch
- For the Cookie Dough: - Nice soft butter - Granulated sugar - Good egg - Real vanilla - Normal all-purpose flour - Pinch of salt and baking powder

Jump Into Baking
- Bake Until Golden:
- Pop 'em in the oven let them get that hint of brown at the edges then leave them to cool down before touching.
- Shape Your Cookies:
- Form dough balls flatten them then stick on the pineapple mix plus a cherry on top.
- Whip Up the Dough:
- Mash together butter and sugar mix in the egg and vanilla then add flour, baking powder, and salt.
- Fix the Topping:
- Blend pineapple that's drained with brown sugar just leave it aside until ready.
Insider Tricks
Give that pineapple a good squeeze so everything stays crisp. Dough getting soft? Pop it in the fridge for a bit. Gently stick down your toppings and if you love a little bling add some festive sprinkles on top.
Storing Tips
They'll stay yummy for three days on the counter in a sealed box or even longer in the fridge—about a week. Freezing? No problem, just layer them between parchment and they'll hold up great.
Fast Help
- Fresh pineapple's cool just drain it really well
- Brown sugar works best but honey is fine too
- Need to prep? The dough can chill ahead
- Toppings sliding off? Nudge them in with your finger
Cheery Holiday Fun
These little gems are so bright and happy, they totally liven up any holiday bake. Super chill to make but they always wow on the table. Try 'em and they might just become your next Christmas tradition!
Common Questions
- → How come you need to drain the pineapple?
If there's too much juice, the cookies spread out too far and won't have the right chew.
- → Is it a must to chill the dough?
You don't have to, but if things get sticky, pop it in the fridge for 15–20 minutes to make it easier to work with.
- → Can I bake these in advance?
Totally—as long as you tuck them in an airtight box with some wax paper. They'll taste good for five days.
- → Do these cookies freeze nicely?
Best enjoyed right away since the fruity toppings get weird in the freezer.
- → What can I do to make them pop for the holidays?
Try sprinkling on red and green sugar before baking so they glitter for the season.