Pineapple Upside Sugar Cookies Recipe

There’s something undeniably nostalgic about pineapple upside-down cake — the buttery brown sugar, the tangy-sweet pineapple, and the classic maraschino cherry on top. Now, imagine all of that tropical goodness transformed into a soft, chewy, and delightfully fruity cookie. That’s exactly what you get with these Pineapple Upside Sugar Cookies.

These cookies combine the comfort of an old-fashioned sugar cookie with the vibrant, sunny flavors of a tropical dessert. Crushed pineapple and shredded coconut bring sweetness and texture to the dough, while a brown sugar coating caramelizes slightly during baking for a nod to the original upside-down treat. Add a maraschino cherry in the center and you’ve got a show-stopping cookie that’s perfect for summer parties, bake sales, or just brightening a cloudy day.

Why You’ll Love Pineapple Upside Sugar Cookies

• Tropical Twist on a Classic: Combines pineapple upside-down cake with soft sugar cookies.
• No Chill Time: Ready to bake in under 20 minutes.
• Fun & Festive: Great for luaus, pool parties, or themed desserts.
• Soft & Chewy Texture: Thanks to creamed butter and just the right ratio of ingredients.
• Customizable: Add lime zest, swap cherries for candied ginger, or use toasted coconut.
• Freezer Friendly: Bake ahead and store for later enjoyment.

Ingredients You’ll Need

• 1 cup unsalted butter, softened
  Ensure it’s soft but not melted for best creaming.
• 1 cup granulated sugar
  Provides sweetness and structure.
• 1 large egg
  Binds the dough and adds richness.
• 1 teaspoon vanilla extract
  Enhances all the other flavors.
• 2 ½ cups all-purpose flour
  Spoon and level to avoid dense cookies.
• ½ teaspoon baking powder
  Adds a gentle lift.
• ¼ teaspoon salt
  Balances sweetness and boosts flavor.
• ½ cup crushed pineapple, well-drained
  Too much moisture can make the dough soggy.
• ½ cup brown sugar (for rolling)
  Creates a caramelized crust when baked.
• ¼ cup unsweetened shredded coconut
  Adds tropical flair and texture.
• Maraschino cherries (optional)
  Aesthetic and flavor bonus — classic upside-down cake touch.

Step-by-Step Instructions

1. Preheat your oven.
Set your oven to 350°F (175°C). Line two baking sheets with parchment paper.

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.

3. Add wet ingredients.
Beat in the egg and vanilla extract until the mixture is smooth and well combined.

4. Mix dry ingredients.
In a separate bowl, whisk together the flour, baking powder, and salt.

5. Combine wet and dry.
Gradually add the dry ingredients to the butter mixture, mixing just until combined. Don’t overmix.

6. Fold in pineapple and coconut.
Gently stir in the well-drained crushed pineapple and shredded coconut until evenly distributed.

7. Prepare brown sugar coating.
In a small bowl, mix the brown sugar with 1-2 teaspoons of flour. This 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 completely coated.

10. Place and flatten.
Arrange the cookies on the baking sheets about 2 inches apart. Flatten slightly with your palm or the bottom of a glass.

11. Add cherries (optional).
Press a maraschino cherry into the center of each cookie, if desired.

12. Bake.
Bake for 12-15 minutes, or until the edges are golden and the tops are just set. The centers should still be soft.

13. Cool.
Let cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Serving and Storage Tips

Serving Ideas:

• Serve chilled for a firmer texture or slightly warm for a softer bite.
• Pair with tropical drinks like pineapple juice, coconut milk, or iced tea.
• Use for ice cream sandwiches with vanilla or coconut ice cream.

Storage:

• Store in an airtight container at room temperature for up to 5 days.
• Place parchment paper between layers to prevent sticking.

Freezing:

• Freeze baked cookies in a single layer, then transfer to a bag. Thaw at room temp.
• You can also freeze the unbaked dough balls — just roll and flatten before freezing. Bake straight from frozen with 1-2 extra minutes.

Helpful Notes

• Drain the Pineapple Thoroughly: Press it gently in a strainer to remove excess moisture.
• Use Unsweetened Coconut: Sweetened coconut can make the cookies too sugary.
• Add Lime Zest: For a citrusy zing, add 1 teaspoon of finely grated lime zest to the dough.
• Toasted Coconut Option: Toast the shredded coconut in a dry pan for added flavor and crunch.
• Glaze Option: Drizzle with a simple glaze of powdered sugar and pineapple juice for a decorative finish.

Frequently Asked Questions

1. Can I use canned pineapple chunks instead of crushed?
You can, but you’ll need to chop them finely and drain them thoroughly. Crushed pineapple is easier and more consistent in the dough.

2. What if I don’t like coconut?
You can omit the coconut entirely or replace it with chopped nuts or extra flour (2-3 tablespoons).

3. How do I keep the cookies from spreading too much?
If your dough feels too soft, chill it for 20-30 minutes before baking. Also ensure the pineapple is not too wet.

4. Can I make these gluten-free?
Yes! Use a 1:1 gluten-free all-purpose flour blend.

5. Are maraschino cherries necessary?
No, but they add a pop of color and flavor. You can substitute with dried pineapple chunks or leave them off entirely.

Final Thoughts

Pineapple Upside Sugar Cookies are a delightful mash-up of two beloved desserts: the nostalgic sugar cookie and the tropical pineapple upside-down cake. These cookies are buttery, soft, and full of flavor, with sweet pineapple and coconut in every bite and a caramelized sugar coating for a little crunch.

They’re easy enough for everyday baking but unique enough to bring to a special event or festive gathering. I’ve made them for spring brunches, summer BBQs, and even as cheerful holiday cookies, and they always get rave reviews.

Give these a try, especially if you’re looking for something a little different yet incredibly satisfying. And don’t forget to share them — though you may find yourself keeping most of the batch for yourself!