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### 🛒 Ingredients You’ll Need
For the cookie dough:
– 1 cup **unsalted butter**, softened
– 1 cup **granulated sugar**
– 1 **large egg**
– 2 tsp **vanilla extract**
– 2 ½ cups **all-purpose flour**
– ½ tsp **baking soda**
– ½ tsp **salt**
For the topping:
– 1 cup **crushed pineapple** or finely diced pineapple
– ¼ cup **brown sugar**
– 10–12 **maraschino cherries**, halved
– Optional: 2 tbsp **pineapple juice** for extra flavor
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### 👩🍳 How to Make Them
#### 1. **Prepare the Pineapple Topping**
In a small saucepan, combine:
– 1 cup pineapple (drained well)
– ¼ cup brown sugar
– Optional: 2 tbsp pineapple juice
Cook over medium heat for 5–7 minutes until the mixture thickens slightly and becomes syrupy. Set aside to cool.
#### 2. **Make the Sugar Cookie Dough**
1. Preheat oven to **350°F (175°C)**.
2. In a large bowl, cream the **butter** and **sugar** until light and fluffy.
3. Add the **egg** and **vanilla extract**, and beat until combined.
4. In a separate bowl, whisk together **flour**, **baking soda**, and **salt**.
5. Gradually mix the dry ingredients into the wet mixture until a dough forms.
#### 3. **Assemble the Cookies**
1. Line a baking sheet with parchment paper.
2. Scoop out 1½ tbsp-sized portions of dough and roll into balls.
3. Slightly flatten each ball and use your thumb or a spoon to make a **shallow well** in the center.
4. Spoon a small amount of the **pineapple mixture** into the well.
5. Top with **half a cherry** in the center.
#### 4. **Bake**
Bake for **12–14 minutes**, or until the edges are just golden. Let them cool on the pan for 5 minutes before transferring to a wire rack.
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### 💡 Tips for Cookie Success
– **Drain pineapple well** to prevent sogginess.
– Don’t overfill the centers—just a teaspoon or so of pineapple topping is enough.
– These cookies are best served **fresh** but can be stored in an airtight container for up to 3 days.
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### 🌞 Why You’ll Love Pineapple Upside Sugar Cookies
✔️ A fun tropical twist on a classic
✔️ Sweet, fruity, and colorful
✔️ Great for parties or gifting
✔️ Kid-friendly and easy to make
✔️ No fork or plate required!
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### 🍪 Serving Suggestions
– Serve them with **vanilla ice cream** for a pineapple sundae cookie treat.
– Pair with a **tropical drink or iced tea** for a summer vibe.
– Dust with **powdered sugar** for a decorative finish.
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### Final Thoughts: A Sweet Island Escape in Every Bite
Pineapple Upside Sugar Cookies are the kind of treat that brings a smile with every bite. They’re cheerful, easy to make, and taste like a **mini vacation** in cookie form. Whether you’re baking for a special occasion or just treating yourself, this fun twist on two classic desserts is sure to become a favorite.
Want to make them gluten-free or try a cherry-free version? Let me know—I’ve got sweet solutions for every preference! 🍍💛🍒
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