Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert. They combine the sweet and tropical flavor of pineapple with the familiar comfort of a sugar cookie. Perfect for busy days, these cookies are simple to make and offer a fun way to enjoy the taste of pineapple upside-down cake in a handheld treat.
Recipe Information
Prep Time: 15 minutes
Cook Time: 12-15 minutes
Total Time: 30 minutes
Servings: 24
Difficulty Level: Easy
Nutrition Information (per serving)
Calories: 120
Protein: 1g
Carbohydrates: 18g
Fat: 6g
Fiber: 0g
Sugar: 6g
Sodium: 50mg
Why Make Pineapple Upside Down Sugar Cookies
These Pineapple Upside Down Sugar Cookies are not just delicious; they are also a great way to bring some tropical flair to your dessert table. Made with wholesome ingredients, they can be customized to suit your taste or occasion. With a mix of fruity sweetness and a hint of caramel from the brown sugar, they offer a unique flavor profile that both kids and adults will love.
How to Make Pineapple Upside Down Sugar Cookies Step by Step
Ingredients
1/2 cup unsalted butter, softened
3/4 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
1 1/2 cups all-purpose flour
1/2 teaspoon baking powder
1/4 teaspoon salt
1/4 cup crushed pineapple, drained
Maraschino cherries, halved
Brown sugar, for sprinkling
Directions
- Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
- In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
- Beat in the egg and vanilla extract until well combined.
- In a separate bowl, whisk together the flour, baking powder, and salt.
- Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
- Scoop tablespoon-sized portions of dough onto the prepared baking sheet, spacing them about 2 inches apart.
- Flatten each dough ball slightly with the back of a spoon or your fingers.
- Place a small spoonful of crushed pineapple on top of each cookie, then top with a cherry half.
- Lightly sprinkle a pinch of brown sugar over the pineapple and cherry.
- Bake for 12-15 minutes, or until the edges are lightly golden.
- Allow the cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

How to Serve Pineapple Upside Down Sugar Cookies
These cookies can be enjoyed warm or at room temperature. They pair beautifully with a scoop of vanilla ice cream for a delightful dessert. Consider serving them alongside fresh fruit or a light salad to balance the sweetness.
How to Store Pineapple Upside Down Sugar Cookies
Store any leftover cookies in an airtight container at room temperature for up to a week. If you want to keep them longer, you can freeze the cookies. Place them in a freezer bag, separating layers with parchment paper. When ready to enjoy, thaw at room temperature or warm in the microwave for a few seconds.
Expert Tips for Cooking Pineapple Upside Down Sugar Cookies
- Use fresh pineapple if available for an even brighter flavor.
- Don’t skip draining the crushed pineapple; excess moisture can affect the cookie’s texture.
- Try adding a pinch of cinnamon to the dough for a warm spice that complements the pineapple.
- For fun, mix in some chopped walnuts or pecans for added crunch.
- Keep an eye on the cookies while baking; each oven can vary, and you want them lightly golden for the best texture.
Delicious Variations of Pineapple Upside Down Sugar Cookies
For a unique twist, consider adding some coconut flakes to the dough for a tropical vibe. You could also swap out the cherries for other fruits like diced strawberries or blueberries for a fruity surprise. If you enjoy a bit of heat, try adding a dash of cayenne pepper or chili powder to the dough for a spicy kick.
Pineapple Upside Down Sugar Cookies are a must-try for anyone who enjoys easy and delicious baking. Their tropical flavor is a hit for any occasion, and the simplicity of the recipe makes them perfect for bakers of all levels. Enjoy making and sharing these delightful treats!






