If you’re looking to bring a festive twist to your cookie tray this holiday season, the Christmas Pineapple Upside-Down Sugar Cookies Recipe is a true showstopper. Imagine buttery, soft sugar cookies with little bursts of sweet pineapple and the classic bright tang from maraschino cherries nestled right on top. This recipe captures the nostalgic charm of the old-fashioned pineapple upside-down cake but in a delicate, handheld cookie format that everyone will adore. Perfectly balanced between tender crumb and juicy fruit, these cookies aren’t just delicious—they’re a joyful celebration on your tongue and at your holiday table.

Christmas Pineapple Upside-Down Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

This recipe keeps things straightforward but relies on essential pantry staples that work beautifully together. Each ingredient plays a special part, from richness to texture to that iconic pineapple-cherry combo that brings the magic alive.

Unsalted butter (1/2 cup + 1/2 cup, softened): Provides the perfect tender, melt-in-your-mouth texture.
Granulated sugar (3/4 cup + 3/4 cup): Sweetens the cookies and helps create a light crumb.
Large egg (1): Binds all ingredients and adds moisture for soft cookies.
Vanilla extract (1 teaspoon): Enhances the overall flavor with warm, sweet notes.
All-purpose flour (1 1/2 cups): The backbone, providing structure for each cookie.
Baking powder (1/2 teaspoon): Gives just enough lift to keep the cookies tender, not flat.
Salt (1/4 teaspoon): Balances sweetness and boosts flavor.
Maraschino cherries (6, halved): The festive garnish that adds color and a juicy pop.
Crushed pineapple (1/4 cup, drained well): Adds moistness and those tropical sweetness bursts.
Brown sugar (2 tablespoons): Enhances the pineapple mixture with deeper caramel tones.

How to Make Christmas Pineapple Upside-Down Sugar Cookies Recipe

Step 1: Preheat and Prepare

First things first, get your oven warmed to 350°F (175°C) and line a baking sheet with parchment paper. This step sets the stage for the cookies to bake evenly without sticking and makes cleanup a breeze.

Step 2: Cream Butter and Sugar

In a large bowl, beat the softened butter with the granulated sugar until the mixture looks pale, light, and fluffy. This creaming process is key for that airy and tender cookie texture. Then, mix in the egg and vanilla extract until everything is combined smoothly.

Step 3: Combine Dry Ingredients

Whisk together the all-purpose flour, baking powder, and salt in a separate bowl. Gradually add this to the wet ingredients, mixing carefully until a soft dough forms. Avoid overmixing to keep your cookies soft and tender.

Step 4: Prepare the Pineapple Mixture

Drain the crushed pineapple well—excess liquid will make the cookies soggy. In a small bowl, mix the pineapple with the brown sugar until the sugar dissolves. This sweet, juicy topping will be the star flavor when added to each cookie.

Step 5: Shape and Top the Cookies

Scoop out about one tablespoon of dough for each cookie. Flatten it gently into a circle on the baking sheet, then add a tiny pinch of the brown sugar and pineapple mixture in the center. Top with half of a maraschino cherry for that signature festive look.

Step 6: Bake to Perfection

Bake your cookies for 10-12 minutes, until the edges just turn golden brown. This ensures a soft center with that delightful crispness around the edges. Once baked, let them cool for 5 minutes on the sheet, then transfer to a wire rack to cool completely before enjoying.

How to Serve Christmas Pineapple Upside-Down Sugar Cookies Recipe

Garnishes

While the maraschino cherry and pineapple topping are already perfect, you could dust your cookies lightly with powdered sugar for a frosty look. Adding a small sprig of mint or edible gold sprinkles can also elevate the holiday charm beautifully.

Side Dishes

These cookies pair wonderfully with a warm cup of spiced tea or a rich cup of hot cocoa. If you’re brunching, why not serve them alongside a tangy cranberry sauce or a dollop of whipped cream? The fruity and sweet elements harmonize effortlessly.

Creative Ways to Present

Arrange the cookies on a festive platter lined with pine needle sprigs or holly leaves for an inviting centerpiece. You could also stack them in a clear jar tied with a red ribbon to gift a homemade holiday treat packed with cheer.

Make Ahead and Storage

Storing Leftovers

Store any leftover Christmas Pineapple Upside-Down Sugar Cookies Recipe in an airtight container at room temperature for up to five days. This keeps them soft and flavorful without drying out, so you’ll have a festive snack ready whenever cravings strike.

Freezing

If you want to prepare ahead or extend their shelf life, freeze the cookies in a sealed container separated with parchment paper to avoid sticking. They will keep well for up to three months and can be thawed at room temperature when you’re ready to indulge.

Reheating

To enjoy these cookies warm, pop them in a preheated oven at 300°F (150°C) for 5 minutes, or microwave for about 10 seconds. This briefly revives their softness and brings out that pineapple aroma, making them taste freshly baked once again.

FAQs

Can I use fresh pineapple instead of canned crushed pineapple?

Absolutely! Just make sure to drain any excess juice very thoroughly to maintain the right dough consistency and prevent sogginess. Fresh pineapple adds an even brighter, fresher flavor.

What’s the best way to soften butter for this recipe?

For perfectly softened butter, leave it at room temperature for about 30-60 minutes. It should be soft enough to press a finger into easily but not melted. If you’re short on time, a few seconds in the microwave on low power works too.

Can I make these cookies gluten-free?

You can swap the all-purpose flour for a gluten-free baking blend that is a one-to-one substitute. Just check that your blend includes xanthan gum or another binder to keep the texture just right.

Why do these cookies need both granulated and brown sugar?

The granulated sugar helps create that classic sugar cookie crunch and sweetness, while the brown sugar adds moisture and a deep caramel flavor—especially important for complementing the pineapple topping.

How long do these cookies keep their freshness?

They’re best enjoyed within five days of baking if stored properly at room temperature. Beyond that, they may start to dry out, but freezing is always an excellent option if you want to keep them longer.

Final Thoughts

There’s something truly magical about the Christmas Pineapple Upside-Down Sugar Cookies Recipe that brightens any holiday moment. With its perfect blend of festive colors, mouthwatering flavors, and that nostalgic nod to classic pineapple upside-down cake, this recipe is destined to become a treasured tradition. I can’t wait for you to try it and share the joy it brings to your holiday gatherings!