Name: Pineapple Upside Sugar Cookies Recipe
Prep time: 15 min
Cook time: 12 min
Total time: 27 min
Cuisine: American
Ingredients: 1/2 cup unsalted butter (softened); 3/4 cup granulated sugar; 1 large egg; 1/2 teaspoon vanilla extract; 1 1/2 cups all-purpose flour; 1/2 teaspoon baking soda; 1/4 teaspoon salt; 1/3 cup crushed pineapple (drained well); 1/4 cup light brown sugar; 6 maraschino cherries (halved); extra granulated sugar for rolling (optional)

Jump to Recipe·Print Recipe

If you’re looking to bring a little sunshine to your baking, these Pineapple Upside Sugar Cookies are an absolute must-try. Imagine all the nostalgic delight of a pineapple upside-down cake, but wrapped up in a golden, chewy cookie bursting with tropical flavor. Each bite is loaded with sweet pineapple, a hint of brown sugar caramel, and topped with that classic maraschino cherry. Whether you’re making them for a backyard barbecue or just to brighten someone’s day, Pineapple Upside Sugar Cookies deliver pure joy in every dreamy bite.

Pineapple Upside Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

The beauty of Pineapple Upside Sugar Cookies lies in their simplicity: every ingredient plays a starring role. From a pillowy-soft sugar cookie dough to the juicy touch of pineapple and that signature cherry on top, each component brings something special to this sunny treat.

Unsalted butter (1/2 cup, softened): Gives the cookies rich flavor and the perfect, tender texture.
Granulated sugar (3/4 cup): Adds classic sweetness and helps create a soft crumb.
Egg (1 large): Binds the dough, delivering that signature cookie chew.
Vanilla extract (1/2 teaspoon): Amplifies the warmth and rounds out the flavors.
All-purpose flour (1 1/2 cups): Forms the structure of the cookie, keeping them sturdy yet tender.
Baking soda (1/2 teaspoon): Gives the cookies lift and a light, cakey rise.
Salt (1/4 teaspoon): Balances out the sweetness and boosts all the flavors.
Crushed pineapple (1/3 cup, drained well): The hero ingredient; adds juicy, tangy pockets of fruit and tropical flair.
Light brown sugar (1/4 cup): Creates a lovely caramelized layer on the bottom of each cookie, reminiscent of classic upside-down cakes.
Maraschino cherries (6, halved): That pop of color and retro charm right in the center.
Extra granulated sugar (optional, for rolling): Quickly adds crisp edges and a sparkly finish.

How to Make Pineapple Upside Sugar Cookies

Step 1: Prepare the Baking Sheet and Preheat

Start with a little kitchen prep! Preheat your oven to 350°F (175°C), and line a baking sheet with parchment paper. This makes sure nothing sticks and cleanup is a breeze. It’s a small step that makes a big difference.

Step 2: Cream the Butter and Sugar

In a large bowl, use an electric mixer to cream the softened butter and granulated sugar until the mixture turns pale and fluffy. Be patient here; this step gives you that dreamy, melt-in-your-mouth texture we all love in Pineapple Upside Sugar Cookies.

Step 3: Mix in Egg and Vanilla

Add the large egg and vanilla extract right into your butter mixture, beating until everything is smooth and fully blended. This simple step infuses the dough with warmth and subtle complexity.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together flour, baking soda, and salt. This ensures the leavening agents are evenly dispersed, so each cookie puffs up perfectly in the oven.

Step 5: Make the Dough & Add Pineapple

Gradually mix the dry ingredients into the wet mixture. As soon as a dough forms, gently fold in the well-drained, crushed pineapple. If your pineapple is too wet, you’ll get soggy cookies — so press out any excess juice for that ideal texture in every Pineapple Upside Sugar Cookie.

Step 6: Shape and Sugar the Cookies

Scoop tablespoon-sized balls of dough and gently roll them. Dip the bottom of each ball into a small bowl of light brown sugar, then place them sugar-side-down on your prepared baking sheet. This creates that irresistible caramelized base reminiscent of traditional upside-down desserts.

Step 7: Add the Cherry on Top

To get the signature look, press a cherry half right into the center of each dough ball. It’s that fun, whimsical touch that makes Pineapple Upside Sugar Cookies feel so festive and retro.

Step 8: Bake & Cool

Bake for 10 to 12 minutes or until the edges are just golden and the tops are set. Let the cookies rest on the baking sheet for about 5 minutes before gently transferring them to a wire rack to finish cooling. This helps them finish setting up and makes them easy to handle.

How to Serve Pineapple Upside Sugar Cookies

Garnishes

Pineapple Upside Sugar Cookies are gorgeous as-is, but a tiny dusting of extra granulated sugar before baking adds sparkle. For a special touch, serve them with an extra cherry or a light drizzle of pineapple glaze right before serving — the colors pop and the flavors really sing!

Side Dishes

Pair these cookies with vanilla bean ice cream, tangy Greek yogurt, or a fruit salad bursting with mango and fresh pineapple. For afternoon tea, they’re stellar with a tall glass of iced tea or a fruity mocktail to complete the tropical vibe.

Creative Ways to Present

Bring a tray of Pineapple Upside Sugar Cookies to your next summer party arranged on a colorful platter, or stack them in cellophane bags tied with raffia for a charming homemade gift. They’re delightful when served alongside mini pineapple upside-down cake pops at a dessert bar!

Make Ahead and Storage

Storing Leftovers

Keep cooled Pineapple Upside Sugar Cookies in an airtight container at room temperature for up to three days. If you need them to last a bit longer, slide a slice of bread in with the cookies to help maintain their softness. The cookies remain buttery and tender, with that signature caramelized sugar base still intact.

Freezing

Want to stock up for future cravings? Place fully cooled cookies in a single layer in a freezer-safe bag, adding parchment between layers to prevent sticking. They’ll stay delicious in the freezer for up to two months. Thaw at room temperature and enjoy!

Reheating

If you love a just-baked texture, pop a cookie or two in the microwave for a few seconds to restore their soft and chewy bite. Be careful not to overheat — just enough to wake up those dreamy pineapple flavors.

FAQs

Can I use fresh pineapple instead of canned?

Yes, you absolutely can! Just be sure to crush it finely and drain off as much liquid as possible. Too much moisture from fresh pineapple can alter the dough’s texture, so give it a thorough squeeze before folding it in.

What’s the best way to drain crushed pineapple?

Pour the crushed pineapple into a fine mesh strainer and press gently with the back of a spoon to release excess juice. You want the pineapple pieces to be moist but not dripping — this helps the Pineapple Upside Sugar Cookies bake up perfectly instead of turning soggy.

Can I make the dough ahead of time?

Definitely! The dough can be made and refrigerated up to 24 hours in advance. When ready to bake, let it soften slightly at room temperature for easier scooping and shaping.

Do I have to use maraschino cherries?

Not at all. While those glossy red cherries are traditional and eye-catching, you can swap in candied pineapple chunks or even omit the topping if you prefer a more streamlined look.

How do I get a stronger pineapple flavor?

If you want a bold, punchy pineapple taste, add 1/4 teaspoon pineapple extract to your dough. It’s a simple way to boost the tropical notes in these Pineapple Upside Sugar Cookies!

Final Thoughts

Bake up a batch of Pineapple Upside Sugar Cookies and share a little taste of sunshine, no matter the season. They’re easy, bursting with fun flavors, and guaranteed to bring smiles. Give them a try — you’re just a few steps away from your new favorite cookie!

Pineapple Upside Sugar Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star

4.8 from 9 reviews

Author: admin
Total Time: 27 minutes
Yield: 12 cookies 1x
Diet: Vegetarian

Print Recipe

Description

Indulge in a tropical twist on classic sugar cookies with these delightful Pineapple Upside Sugar Cookies. Soft and chewy cookies infused with pineapple flavor, topped with a sweet brown sugar crust and a juicy maraschino cherry. Perfect for a sweet treat or special occasion!

Ingredients

Scale

Cookies:

1/2 cup unsalted butter (softened)
3/4 cup granulated sugar
1 large egg
1/2 teaspoon vanilla extract
1 1/2 cups all-purpose flour
1/2 teaspoon baking soda
1/4 teaspoon salt
1/3 cup crushed pineapple (drained well)

Topping:

1/4 cup light brown sugar
6 maraschino cherries (halved)
extra granulated sugar for rolling (optional)

Cook Mode Prevent your screen from going dark

Instructions

Preheat Oven: Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
Cream Butter and Sugar: In a large bowl, cream the butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until smooth.
Mix Dry Ingredients: In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry mixture to the wet ingredients, mixing until combined. Fold in the crushed pineapple.
Prepare Topping: In a small bowl, place the brown sugar. Roll tablespoon-sized balls of dough, press the bottom into the brown sugar, and place sugar-side-down on the baking sheet. Press a cherry half gently into the center of each cookie.
Bake: Bake for 10-12 minutes or until lightly golden. Cool on the baking sheet for 5 minutes before transferring to a wire rack.