Pineapple Upside Sugar Cookies

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If you love the buttery sweetness of sugar cookies and the bright, tangy flavor of pineapple, these Pineapple Upside Sugar Cookies are your perfect match. Each cookie features a soft, chewy base topped with caramelized pineapple and a hint of cinnamon—bringing tropical flair to your dessert table. Whether you’re baking for a potluck, a party, or just a sweet moment at home, these cookies are sure to turn heads and warm hearts.

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💛 Why You’ll Love Them

  • Tropical & Tangy: Caramelized pineapple adds juicy brightness to every bite.
  • Soft & Chewy: The sugar cookie base is tender and buttery, with just the right texture.
  • Quick & Easy: Ready in under 30 minutes—ideal for spontaneous baking sessions.
  • Customizable: Add nuts, coconut, or a drizzle of glaze to make them your own.

🛒 Ingredients (Makes 12–16 Cookies)

Component Ingredient Amount Notes
Topping Fresh pineapple (or canned rings) 1, peeled, cored, sliced thin Use canned if short on time
Unsalted butter, melted 2 tablespoons
Brown sugar 2 tablespoons
Ground cinnamon (optional) ¼ teaspoon Adds warmth and depth
Cookie Dough Unsalted butter, softened 1 cup
Granulated sugar 1 cup
Large egg 1
Pure vanilla extract 1 teaspoon
All-purpose flour 2¼ cups
Baking powder 1 teaspoon
Salt ¼ teaspoon

👩‍🍳 How to Make Them

1. Preheat the Oven
Set oven to 350°F (175°C).
Line a baking sheet with parchment paper or lightly grease it.

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2. Prepare the Topping
Brush each pineapple slice with melted butter.
Sprinkle with brown sugar and cinnamon (if using).
Place on the baking sheet, spaced apart.

3. Make the Cookie Dough
Cream butter and sugar until light and fluffy.
Beat in egg and vanilla.
In a separate bowl, whisk flour, baking powder, and salt.
Gradually mix dry ingredients into wet until a soft dough forms.

4. Assemble the Cookies
Scoop 1–2 tablespoons of dough and flatten slightly.
Place each dough round on top of a pineapple slice, pressing gently to seal the edges.

5. Bake
Bake for 12–15 minutes, until edges are golden.
Cool on the baking sheet for 2–3 minutes.

6. Flip & Finish
Carefully flip each cookie so the pineapple is on top.
Optional: Drizzle with glaze (powdered sugar + milk) or sprinkle with shredded coconut.

🌟 Tips for Success

  • Go Fresh: Fresh pineapple caramelizes beautifully, but canned rings work well too.
  • Add Crunch: Try chopped macadamia nuts or pecans for texture.
  • Flavor Swap: Use coconut sugar instead of brown sugar for a deeper caramel note.
  • Storage: Keep in an airtight container at room temp for 2 days or refrigerate up to 5. Bring to room temp before serving.

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