Pineapple Upside Sugar Cookies

The moment I pulled out the mixing bowl to make Pineapple Upside Sugar Cookies, I was suddenly seven again, kneeling beside Grandma's stove while the aroma of brown sugar and pineapple drifted through the air. Just like the classic pineapple upside‑down cake-with its caramelized topping and bright, sweet pineapple-this cookie version brings that same sunny nostalgia into every bite.

This recipe is perfect for spring gatherings, backyard brunches, or just when you're craving a cheerful twist on a familiar sweet. Whether you're planning a pool‑side treat or simply brightening up a rainy afternoon, these cookies deliver the tropical flavor and comforting softness you'll fall in love with.

Why You'll Love Pineapple Upside Sugar Cookies

• Tropical Twist on a Classic: You get the sunshine of pineapple upside‑down cake combined with the comforting softness of a sugar cookie.
• No Chill Time: The dough comes together quickly and you're ready to bake in under 20 minutes-ideal when the craving hits.
• Fun & Festive: With pineapple, coconut, and the option of a maraschino cherry on top, these cookies work beautifully for luau‑themed parties, bake sales or special occasions.
• Soft & Chewy Texture: The creamed butter and just‑right ratio of flour give a tender, chewy bite that's just as good warm as it is cooled.
• Customizable: Feel free to add a sprinkle of lime zest, replace cherries with candied ginger, or use toasted coconut to make your own twist.
• Freezer Friendly: Bake ahead or freeze dough for later-handy when you want cookies without the last‑minute fuss.

Ingredients You'll Need

Here's everything you'll want for these sunny cookies:

• 1 cup unsalted butter, softened - make sure it's soft to the touch but not melted, for proper creaming.
• 1 cup granulated sugar - gives sweetness and structure.
• 1 large egg - binds the dough and adds richness.
• 1 teaspoon vanilla extract - brings out all the flavors.
• 2½ cups all‑purpose flour - spoon & level it to avoid overly dense cookies.
• ½ teaspoon baking powder - gives a gentle lift.
• ¼ teaspoon salt - balances the sweetness and enhances flavor.
• ½ cup crushed pineapple, well drained - excess moisture will make the dough too soft, so drain thoroughly.
• ½ cup brown sugar (for rolling) - this creates a caramel‑like crust during baking.
• ¼ cup unsweetened shredded coconut - adds a lovely tropical texture; unsweetened is preferred so it doesn't make the cookies too sugary.
• Maraschino cherries (optional, for garnish) - they add color, flavor and the feel of a true pineapple upside‑down dessert.

Step‑by‑Step Instructions

Here's how to make your Pineapple Upside Sugar Cookies-just follow the steps and you'll have a batch of sunshine on a baking sheet:

1. Preheat the oven.
   • Set your oven to 350 °F (175 °C).
   • Line two baking sheets with parchment paper so your cookies bake evenly and easy release.
2. Cream the butter and sugar.
   • In a large mixing bowl, beat the softened butter and granulated sugar together until light and fluffy (about 2-3 minutes).
   • This step sets the stage for a soft, tender cookie.
3. Add wet ingredients.
   • Beat in the egg and vanilla extract until the mixture is smooth and well combined.
4. Mix the dry ingredients.
   • In a separate bowl, whisk together the flour, baking powder, and salt.
   • This ensures even distribution of leavening and salt.
5. Combine wet and dry.
   • Gradually add the flour mixture into the butter‑sugar‑egg mixture, mixing just until combined. Don't overmix-overworked dough can lead to tougher cookies.
6. Fold in pineapple and coconut.
   • Gently stir the well‑drained crushed pineapple and shredded coconut into the dough until evenly distributed. Don't worry if it looks a little clumpy-this adds texture and flavor.
7. Prepare the brown sugar coating.
   • In a small bowl, mix the brown sugar with 1-2 teaspoons of flour. This little flour addition prevents the sugar from melting too quickly and helps coat the cookies evenly.
8. Scoop and roll dough.
   • Using a tablespoon or cookie scoop, portion out the dough and roll into balls.
9. Coat in brown sugar.
   • Roll each dough ball in the brown sugar mixture until it's completely coated-this gives that caramelized outer bite.
10. Place and flatten.
    • Arrange the dough balls onto the prepared baking sheets, about 2 inches apart so they have room to spread.
    • Flatten each slightly with your palm or the bottom of a glass.
11. Optional cherries.
    • If you'd like the full pineapple upside‑down feel: press a maraschino cherry into the center of each cookie.
12. Bake.
    • Bake for about 12-15 minutes, or until the cookie edges are golden and the tops are just set. The centers should still be a little soft-allowing them to finish setting as they cool.
13. Cool.
    • Let the cookies cool on the baking sheet for about 5 minutes, then transfer to a wire rack to cool completely. This helps them set without losing that delightful chewy texture.

Serving and Storage Tips

Serving

• These cookies are lovely slightly warm (with a soft buttery chew) or chilled (firmer bite) - both have their charm.
• Pair with tropical drinks: pineapple juice, coconut milk smoothies, or iced tea with a wedge of lime can elevate the experience.
• For a special treat: Use them as ice‑cream sandwich bases. A scoop of vanilla or coconut ice cream between two cookies = summer magic.
• Great for parties: Place them on a pretty platter, garnish with extra shredded coconut or pineapple wedges for visual flair.

Storage

• Store in an airtight container at room temperature for up to 5 days. Place parchment paper between layers of cookies to prevent sticking.
• Freezing baked cookies: Freeze in a single layer first, then transfer to a zipped freezer bag or sealed container. Thaw at room temperature when you're ready.
• Freezing unbaked dough: You can freeze dough balls (after rolling in brown sugar) on a tray, then transfer to a bag. When ready, place on parchment‑lined sheet and bake-just add 1-2 minutes to the baking time since they're cold.

Helpful Notes

• Drain the pineapple thoroughly. Excess moisture from pineapple can make the dough too soft and cause spreading. Press it gently in a strainer to remove as much liquid as possible.
• Use unsweetened shredded coconut. Sweetened coconut may make the cookies overly sugary and change texture.
• Add lime zest if you like a citrusy zing. A teaspoon of finely grated lime zest stirred into the dough brightens up the tropical flavor and contrasts beautifully with the sweetness.
• Toasted coconut option: For extra depth, toast the shredded coconut in a dry skillet until golden brown and fragrant-then fold it in. Adds crunch and a nutty note.
• Glaze option: Want a decorative finish? Drizzle a simple glaze made from powdered sugar and pineapple juice over cooled cookies for a sweet sheen.
• Allergy adjustment: If you're gluten‑free, simply use a 1:1 gluten‑free all‑purpose flour blend. If you skip coconut, you can replace it with chopped nuts (like macadamia) or extra flour (2-3 tablespoons) for texture.
• To control spread: If you find your cookies flattening too much, chill the dough for 20-30 minutes before baking. Also verify your pineapple is well drained.

Frequently Asked Questions

1. Can I use canned pineapple chunks instead of crushed?
   Yes - but you'll need to chop the chunks finely so they integrate well into the dough, and be sure to drain them thoroughly. Crushed pineapple is more consistent and easier.
2. What if I don't like coconut?
   No problem - you can omit the coconut entirely, or replace it with chopped nuts (2-3 Tbsp) or extra flour to maintain texture.
3. How do I keep the cookies from spreading too much?
   If the dough feels too soft, chill it for 20-30 minutes. Also make sure the pineapple is well drained so there's minimal extra moisture in the dough.
4. Can I make these gluten‑free?
   Absolutely - swap in a high‑quality 1:1 gluten‑free all‑purpose flour blend in place of the plain flour and proceed as instructed.
5. Are maraschino cherries necessary?
   No, they're optional - they do add a nostalgic look and extra flavor, but you can skip them or substitute with dried pineapple chunks or leave them off entirely.

Final Thoughts

I've made these Pineapple Upside Sugar Cookies many times for family brunches, backyard BBQs, and even holiday cookie swaps-and they always bring a burst of sunshine wherever they go. The sweet pineapple and coconut together with the caramel‑brown sugar coating create a cookie that's easy, unique, and utterly delicious.

Don't hesitate-grab your ingredients, make a batch, and share the love. Let me know how they turn out in the comments and be sure to tag your photo on social media so we can all delight in your tropical treat. Happy baking, and may your kitchen smell like summer!