Why You’ll Love This Recipe

These Pineapple Upside Down Sugar Cookies combine the best of both worlds—soft, sweet sugar cookies with the tangy, tropical flavor of pineapple. The golden edges and slight caramelization from the sugar create a delightful contrast to the juicy, tender pineapple. Whether you’re hosting a party, looking for a new twist on a classic, or simply in the mood for a fun baking project, these cookies will be a hit every time. They’re easy to make, beautiful to serve, and perfect for satisfying your sweet tooth!

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

Cookie Dough Base:

1 cup unsalted butter, softened to room temperature
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract

Dry Ingredients:

2 1/2 cups all-purpose flour
1/2 teaspoon baking soda
1/4 teaspoon salt

Pineapple Topping:

10-12 canned pineapple rings, well-drained and patted completely dry
Extra granulated sugar for sprinkling on top

Directions

Preheat the Oven:
Preheat your oven to 350°F (175°C). Line your baking sheets with parchment paper for easy cleanup.
Make the Dough:
In a large bowl, cream together the softened butter and sugar until light and fluffy. This will take about 3–4 minutes using an electric mixer.
Add the Wet Ingredients:
Beat in the egg and vanilla extract until the mixture is smooth and well combined.
Combine the Dry Ingredients:
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this dry mixture to the wet ingredients, mixing just until a soft dough forms. Be careful not to overmix!
Form the Cookies:
Roll the dough into balls using about 1 1/2 tablespoons for each cookie. Place the dough balls on the prepared baking sheets and gently flatten each one into a disk, leaving plenty of space between cookies.
Add the Pineapple Topping:
Place a pineapple ring on top of each dough disk, pressing it gently into the dough to ensure it stays in place while baking.
Sprinkle Sugar:
Sprinkle a little extra sugar on top of each pineapple ring for that beautiful caramelized sparkle.
Bake the Cookies:
Bake for 12–14 minutes, or until the edges are golden and the cookies are set. For crispier edges, bake for an additional 1–2 minutes.
Cool the Cookies:
Let the cookies cool on the pan for about 5 minutes to set up, then transfer them to a wire rack to cool completely before serving or storing.

Servings and Timing

Servings: 12 (10–12 large cookies)
Prep Time: 20 minutes
Cook Time: 14 minutes
Total Time: 34 minutes

Variations

Add a Cherry: For a more classic upside-down cake look, place a maraschino cherry in the center of each pineapple ring before baking.
Coconut Twist: Add shredded coconut on top of the pineapple for an extra tropical flavor.
Flavored Dough: Mix in cinnamon or nutmeg for a warm spice element in the dough.
Gluten-Free Option: Swap all-purpose flour with a gluten-free flour blend to make these cookies gluten-free.

storage/reheating

Storage: Store cookies in an airtight container at room temperature for up to 4 days. For best texture, enjoy within the first 2 days.
Freezing: To freeze, store the baked cookies in an airtight container or freezer bag. Thaw at room temperature for a few hours before serving.

FAQs

Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple. Just make sure to cut it into rings and pat it dry to avoid excess moisture that could affect the texture of the cookies.

How can I make these cookies even crispier?

To get a crispier texture, bake the cookies for an extra 1-2 minutes until the edges are golden and the pineapple topping is slightly caramelized.

Can I make these ahead of time?

Yes, you can prepare the dough ahead of time and refrigerate it for up to 2 days before baking. Just be sure to bring the dough to room temperature before forming and baking.

Can I use margarine instead of butter?

While butter provides the best flavor and texture, you can substitute margarine if necessary. The texture might be slightly different, but the cookies will still turn out delicious.

Can I add more toppings to the cookies?

Yes! You can add other toppings such as chopped nuts (like walnuts or pecans) or drizzle the cookies with caramel sauce after baking for an extra indulgence.

How do I store leftover cookies?

Store leftover cookies in an airtight container at room temperature for up to 4 days. If you want to keep them fresh longer, freeze them in a container or zip-top bag for up to 2 months.

Can I freeze the dough?

Yes, you can freeze the dough. Roll the dough into balls, place them on a baking sheet to freeze individually, and then transfer to a freezer bag. Bake directly from frozen for a few extra minutes.

Can I make mini versions of these cookies?

Absolutely! Just roll smaller dough balls and adjust the baking time to around 10–12 minutes for mini-sized cookies.

How do I prevent the pineapple from making the cookies soggy?

Make sure to thoroughly drain and pat the pineapple rings dry before adding them to the cookie dough. This helps avoid excess moisture.

What can I serve with these cookies?

These cookies are perfect on their own, but you can serve them with a scoop of vanilla ice cream or a drizzle of caramel sauce for an extra treat.

Conclusion

Pineapple Upside Down Sugar Cookies are a fun and delicious twist on a classic dessert. With a buttery, soft cookie base and a sweet, tropical pineapple topping, they’re sure to become a favorite in your baking rotation. Perfect for any occasion, these cookies are as delightful to look at as they are to eat. Enjoy them with family, friends, or as a treat for yourself!

Pineapple Upside Down Sugar Cookies

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Pineapple Upside Down Sugar Cookies are a delightful and creative twist on the classic pineapple upside-down cake. Featuring a soft, buttery base topped with caramelized pineapple rings, these cookies offer all the flavors of the cake in a handheld form.

Author: Amy
Prep Time: 20 minutes
Cook Time: 14 minutes
Total Time: 34 minutes
Yield: 12 large cookies
Category: Dessert
Method: Baking
Cuisine: American
Diet: Vegetarian

Instructions

Preheat the Oven: Preheat your oven to 350°F (175°C) and line your baking sheets with parchment paper.
Make the Dough: Cream the softened butter and sugar in a large bowl until light and fluffy (3–4 minutes using an electric mixer).
Add Wet Ingredients: Beat in the egg and vanilla extract until smooth and combined.
Combine Dry Ingredients: Whisk together flour, baking soda, and salt in a separate bowl. Gradually add this mixture to the wet ingredients, mixing until just combined (do not overmix).
Form the Cookies: Roll dough into 1 1/2 tablespoon balls, place on the prepared baking sheets, and flatten slightly into disks.
Add the Pineapple Topping: Place a pineapple ring on top of each dough disk, pressing it gently into the dough.
Sprinkle Sugar: Lightly sprinkle extra sugar over each pineapple ring for caramelization.
Bake the Cookies: Bake for 12–14 minutes, or until edges are golden and cookies are set. For crispier edges, bake for 1–2 additional minutes.
Cool the Cookies: Let the cookies cool on the pan for about 5 minutes, then transfer to a wire rack to cool completely before serving or storing.