Pineapple Upside Down Sugar Cookies are a delicious twist on a classic dessert. With their sweet and tropical flavors, these cookies bring a taste of summer to any occasion. The combination of buttery sugar cookie dough topped with juicy pineapple and maraschino cherries makes these treats both fun and delicious. They are easy to make and sure to impress your family and friends!
Why make this recipe
Pineapple Upside Down Sugar Cookies are a great way to enjoy the flavors of the traditional upside-down cake in a cookie form. They are perfect for gatherings, parties, or a sweet snack at home. These cookies are simple to prepare and quick to bake, making them a fantastic choice for bakers of all levels. Plus, they look beautiful and taste amazing!
How to make Pineapple Upside Down Sugar Cookies
Ingredients:
- 1 cup granulated sugar
- 1/2 cup unsalted butter, softened
- 1 large egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1/2 teaspoon baking soda
- 1/2 teaspoon salt
- Pineapple slices (canned or fresh)
- Maraschino cherries
Directions:
- Preheat the oven to 350°F (175°C).
- In a bowl, cream together the sugar and softened butter until fluffy.
- Add the egg and vanilla extract, mixing until well combined.
- In another bowl, whisk together the flour, baking soda, and salt.
- Gradually add the dry ingredients to the wet mixture, stirring until a dough forms.
- On a greased baking sheet, place a pineapple slice in the center of each cookie.
- Place a tablespoon of cookie dough on top of each pineapple slice and gently press down.
- Top each cookie with a maraschino cherry in the middle of the pineapple slice.
- Bake for 12-15 minutes or until the edges are golden.
- Remove from the oven and let cool on a wire rack.

How to serve Pineapple Upside Down Sugar Cookies
These cookies can be served warm or at room temperature. For an extra treat, try serving them with a scoop of vanilla ice cream or whipped cream. They make great additions to dessert trays and can be enjoyed on their own or with a cup of tea or coffee.
How to store Pineapple Upside Down Sugar Cookies
Store the cookies in an airtight container at room temperature for up to a week. If you want to keep them longer, you can freeze them. Just make sure to place parchment paper between layers to prevent sticking.
Tips to make Pineapple Upside Down Sugar Cookies
- Use fresh pineapple for a vibrant flavor. If using canned, make sure to drain it well.
- Experiment with different toppings such as coconut flakes or chopped nuts for added texture.
- Keep an eye on the cookies while they bake, as baking times may vary depending on your oven.
Variation
For a twist, consider adding a dash of cinnamon or nutmeg to the cookie dough. You can also swap the pineapple for other fruits like peaches or cherries, creating different flavors of upside down cookies.
FAQs
Can I use brown sugar instead of white sugar?
Yes, using brown sugar will add a richer flavor to the cookies.
What can I use instead of maraschino cherries?
You can use fresh cherries or chocolate chips as a substitute.
Can I make the dough ahead of time?
Absolutely! You can prepare the dough and refrigerate it for up to 2 days before baking.

Pineapple Upside Down Sugar Cookies
Ingredients
Method
- Preheat the oven to 350°F (175°C).
- In a bowl, cream together the sugar and softened butter until fluffy.
- Add the egg and vanilla extract, mixing until well combined.
- In another bowl, whisk together the flour, baking soda, and salt.
- Gradually add the dry ingredients to the wet mixture, stirring until a dough forms.
- On a greased baking sheet, place a pineapple slice in the center of each cookie.
- Place a tablespoon of cookie dough on top of each pineapple slice and gently press down.
- Top each cookie with a maraschino cherry in the middle of the pineapple slice.
- Bake for 12-15 minutes or until the edges are golden.
- Remove from the oven and let cool on a wire rack.