Craving a sweet treat that’s as delightful as it is diet-friendly? These Pineapple Upside Sugar Cookies combine the tropical flavors of pineapple with the comforting sweetness of sugar cookies. Perfectly portioned and guilt-free, they’re a refreshing twist on a classic dessert, offering a nostalgic flavor with fewer calories.
Ingredients
- 1 cup all-purpose flour (or a mix of whole wheat and all-purpose for added fiber)
- 1/4 teaspoon baking powder
- 1/8 teaspoon baking soda
- Pinch of salt
- 1/4 cup unsalted light butter, softened
- 1/4 cup granulated sugar substitute (like Stevia or Monk Fruit)
- 1 large egg white
- 1 teaspoon vanilla extract
- 2 tablespoons unsweetened pineapple juice
- 6 pineapple rings, cut in half
- 12 maraschino cherries, optional (no-sugar-added preferred)
Instructions
Prepare the Dough
- Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
- In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.
- In a separate bowl, cream together the light butter and sugar substitute until light and fluffy.
- Beat in the egg white, vanilla extract, and pineapple juice until well combined.
- Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
Shape the Cookies
- Using a spoon or cookie scoop, drop rounded tablespoons of dough onto the prepared baking sheet, spacing them about 2 inches apart.
- Gently press a half pineapple ring onto each cookie, making sure it adheres to the dough. Place a maraschino cherry in the center of each pineapple half, if desired.
Bake
- Bake the cookies for 10-12 minutes, or until the edges are lightly golden and the centers are set.
- Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

Nutritional Information
(Per Cookie)
- Calories: ~70
- Protein: 1g
- Carbohydrates: 10g
- Fat: 2g
- Fiber: 0.5g
- WW Points: ~2-3 (depending on specific ingredients used)
Why You’ll Love This Recipe
- Tropical Twist: Pineapple adds a natural sweetness that pairs perfectly with the cookie base.
- Portion-Controlled: Small, individual servings make it easy to stick to your plan.
- Customizable: Add a sprinkle of coconut flakes or swap maraschino cherries for fresh ones to suit your taste.
- Quick and Easy: Perfect for last-minute desserts or snacks, with minimal prep time.
Tips for Success
- Choose the Right Pineapple: Use fresh or canned pineapple packed in juice, not syrup, to keep the points low.
- Chill the Dough: If the dough feels too sticky, refrigerate it for 15-20 minutes before scooping.
- Even Sizing: Use a cookie scoop to ensure uniform-sized cookies that bake evenly.
- Storage: Store cookies in an airtight container in the refrigerator for up to 3 days.
Serving Suggestions
These cookies are delightful on their own, but you can elevate them with these serving ideas:
- Pair with a dollop of light whipped topping or a drizzle of sugar-free caramel sauce.
- Serve alongside a scoop of Weight Watchers-friendly vanilla ice cream for a decadent dessert.
- Enjoy with a cup of iced herbal tea or light pineapple mocktail for a refreshing pairing.
The Pineapple Upside Sugar Cookies are a fun and fruity way to satisfy your sweet tooth while staying on track. Perfect for parties, picnics, or a simple treat at home, they bring a tropical vibe to your dessert table. Light, flavorful, and easy to make, they’re a must-try recipe for any cookie lover!
Tropical Pineapple Upside Sugar Cookies You Need to Try
12-15
servings15
minutes10
minutes70
kcalIngredients
1 cup all-purpose flour (or a mix of whole wheat and all-purpose for added fiber)
1/4 teaspoon baking powder
1/8 teaspoon baking soda
Pinch of salt
1/4 cup unsalted light butter, softened
1/4 cup granulated sugar substitute (like Stevia or Monk Fruit)
1 large egg white
1 teaspoon vanilla extract
2 tablespoons unsweetened pineapple juice
6 pineapple rings, cut in half
12 maraschino cherries, optional (no-sugar-added preferred)
Instructions
- Prepare the Dough
Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.
In a separate bowl, cream together the light butter and sugar substitute until light and fluffy.
Beat in the egg white, vanilla extract, and pineapple juice until well combined.
Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms. - Shape the Cookies
Using a spoon or cookie scoop, drop rounded tablespoons of dough onto the prepared baking sheet, spacing them about 2 inches apart.
Gently press a half pineapple ring onto each cookie, making sure it adheres to the dough. Place a maraschino cherry in the center of each pineapple half, if desired. - Bake
Bake the cookies for 10-12 minutes, or until the edges are lightly golden and the centers are set.
Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.
Notes
- Choose the Right Pineapple: Use fresh or canned pineapple packed in juice, not syrup, to keep the points low.
Chill the Dough: If the dough feels too sticky, refrigerate it for 15-20 minutes before scooping.
Even Sizing: Use a cookie scoop to ensure uniform-sized cookies that bake evenly.
Storage: Store cookies in an airtight container in the refrigerator for up to 3 days.