Festive Holiday Cookies

As seen on: Delicious Dessert Recipes

Make your own mini version of classic pineapple cake. Each soft cookie bursts with sweet pineapple brown sugar and a bright cherry on top—everyone's favorite for the holidays.

emilyscooks.com
Shared By Emily
Last revised on Thu, 17 Jul 2025 18:13:21 GMT
Some pineapple upside-down cookies stacked on a plate, each topped with a bright red cherry. Save this
Some pineapple upside-down cookies stacked on a plate, each topped with a bright red cherry. | emilyscooks.com

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
Stack of pineapple-topped sweets on a festive plate, bright cherries on top, showing off their caramel edges. Save this
Stack of pineapple-topped sweets on a festive plate, bright cherries on top, showing off their caramel edges. | emilyscooks.com

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.

Pineapple Cookies

Tender sugar cookies loaded with juicy pineapple and cheery cherries. A fun twist on the old-school upside-down cake, ready for your Christmas table.

Preparation Time
15 Minutes
Cooking Time
12 Minutes
Overall Time
27 Minutes
Shared By: Emily

Meal Type: Desserts

Skill Level: Moderate

Cuisine Style: American

Makes: 24 Portions (24)

Special Diet: Vegetarian-Friendly

What You’ll Need

01 items 2 tbsp brown sugar.
02 items 1/4 cup crushed pineapple, squeezed dry.
03 items 6 maraschino cherries, sliced in half.
04 items 1/4 tsp salt.
05 items 1/2 tsp baking powder.
06 items 1 1/2 cups all-purpose flour.
07 items 1 tsp vanilla extract.
08 items 1 large egg.
09 items 3/4 cup granulated sugar.
10 items 1/2 cup unsalted butter, at room temp.

Steps To Make It

Step 01

Leave cookies on the hot tray for 5 minutes. Move them over to a rack after.

Step 02

Pop in the oven for about 10-12 minutes. Pull them out when the edges look golden.

Step 03

Put a spoonful of the pineapple on every cookie and press a cherry half on top.

Step 04

Gently press down each dough ball. Don’t squish them too much.

Step 05

Scoop dough into 1-inch balls. Give them a couple inches of space on the tray.

Step 06

Set your oven to 350°F. Cover the sheet with parchment paper.

Step 07

Pour the dry stuff into the wet bit by bit. Mix ’til it turns into a dough.

Step 08

Whisk flour, salt, and baking powder in their own bowl.

Step 09

Mix in the egg and then splash in vanilla.

Step 10

Beat together softened butter and sugar so it’s nice and airy.

Step 11

Stir the drained pineapple with brown sugar and leave it at the side for now.

Extra Notes

  1. Squeeze out every drop of juice from your pineapple so the cookies don’t spread everywhere.
  2. If you’re finding the dough hard to handle, chilling it a bit will help.
  3. A pinch of colored sugar looks super fun for parties.
  4. These taste best while fresh and slightly warm.

Essential Tools

  • Wire rack.
  • Electric mixer.
  • Mixing bowls.
  • Parchment paper.
  • Baking sheet.

Allergen Info

Review ingredients carefully for allergens, and consult a healthcare provider if you're unsure.
  • Eggs.
  • Dairy.
  • Wheat/Gluten.

Nutritional Info (Per Serving)

Keep in mind, this data is an estimate and not a substitute for professional dietary advice.
  • Calories: 110
  • Fat Content: 5 grams
  • Total Carbs: 16 grams
  • Protein Content: 1 grams