Pineapple upside down sugar cookies are a delightful treat that brings a tropical twist to the classic cookie experience. With their soft and chewy texture, these cookies capture the essence of a traditional pineapple upside down cake, making them a fun and unique dessert option. Ideal for gatherings or just a special snack at home, these cookies are sure to impress family and friends. If you love sweet, fruity flavors combined with a satisfying cookie base, you’ll be thrilled to give this recipe a try!
How to prepare Pineapple Upside Down Sugar Cookies
To prepare these mouthwatering cookies, start by gathering the following ingredients:
- 1 cup of unsalted butter, softened
- 1 cup of granulated sugar
- 1 cup of brown sugar, packed
- 2 large eggs
- 1 teaspoon of vanilla extract
- 3 cups of all-purpose flour
- 1 teaspoon of baking soda
- 1/2 teaspoon of salt
- 1 cup of crushed pineapple, drained
- Maraschino cherries for garnish
Once you have all the ingredients ready, follow these easy steps:
- Preheat your oven to 350°F (175°C).
- In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
- Add the eggs, one at a time, mixing well after each addition. Stir in the vanilla extract next.
- In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this dry mixture to the wet ingredients, mixing until just combined.
- Fold in the crushed pineapple until evenly distributed in the dough.
- Drop spoonfuls of cookie dough onto a parchment-lined baking sheet, making sure to space them adequately.
- Press a maraschino cherry into the center of each cookie before baking.
- Bake for 10-12 minutes or until the edges are lightly golden. Remove from the oven and let them cool on a wire rack.

Why You’ll Love Pineapple Upside Down Sugar Cookies
These cookies are not only easy to make, but they also offer a delightful flavor combination that everyone will love. The sweetness of the pineapple pairs perfectly with the rich flavor of the cookie, creating a taste experience that is both refreshing and satisfying. Plus, they are perfect for any occasion, whether you’re hosting a party or just enjoying a cozy night in.
Tips for success
- Make sure to drain the crushed pineapple well so that the cookies don’t become soggy.
- Experiment with adding shredded coconut for an extra tropical touch.
- For a deeper flavor, consider browning the butter before mixing it into the dough.

Serving Suggestions
You can serve these cookies warm, fresh from the oven, or let them cool completely and store them in an airtight container for later. Pair them with a scoop of vanilla ice cream or a dollop of whipped cream for a delicious dessert treat. They also make great snacks for kids and adults alike.
FAQs
1. Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple. Just make sure to finely chop and drain it well.
2. How do I store leftover cookies?
Store the cookies in an airtight container at room temperature for up to a week.
3. Can I freeze these cookies?
Absolutely! You can freeze the unbaked cookie dough for later use, or freeze the baked cookies, wrapping them tightly to maintain freshness.
Additionally, if you’re looking for more delightful dessert ideas, check out this easy banana upside down cake recipe! Enjoy your pineapple upside down sugar cookies!

Pineapple Upside Down Sugar Cookies
Ingredients
Method
- Preheat your oven to 350°F (175°C).
- In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
- Add the eggs, one at a time, mixing well after each addition. Stir in the vanilla extract next.
- In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this dry mixture to the wet ingredients, mixing until just combined.
- Fold in the crushed pineapple until evenly distributed in the dough.
- Drop spoonfuls of cookie dough onto a parchment-lined baking sheet, making sure to space them adequately.
- Press a maraschino cherry into the center of each cookie before baking.
- Bake for 10-12 minutes or until the edges are lightly golden. Remove from the oven and let them cool on a wire rack.
