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+ servings
Plate of Pineapple Upside Down Sugar Cookies with pineapple slices on top

Pineapple Upside Down Sugar Cookies

Deliciously soft and chewy cookies featuring a buttery sugar-cookie base topped with caramelized pineapple, perfect for any occasion.
Prep Time 20 minutes
Cook Time 13 minutes
Total Time 33 minutes
Course Dessert, Snack
Cuisine American, Tropical
Servings 24 cookies
Calories 150 kcal

Ingredients
  

Cookie Base

  • 1 cup unsalted butter, softened Softened at room temperature for easy creaming.
  • 1 cup granulated sugar
  • 1 large egg Use at room temperature for best mixing.
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend) Use a 1:1 cup-for-cup blend that contains xanthan gum for best texture.
  • 1 teaspoon baking soda
  • ½ teaspoon salt

Topping

  • 1 can canned pineapple rings, well-drained Reserve juice for smoothies or marinades.
  • 2 tablespoons additional sugar for sprinkling Sprinkle on top for caramelization.

Instructions
 

Prep and Preheat

  • Preheat your oven to 350°F (175°C) and line a baking tray with parchment or a silicone mat.
  • Drain the canned pineapple rings thoroughly and pat them dry, then trim each ring into 4–6 wedges.

Mix Dry Ingredients

  • In a medium bowl, whisk together flour, baking soda, and salt until well combined. Set aside.

Cream Butter and Sugar

  • In a large bowl, cream the softened butter and granulated sugar until light and fluffy (about 2–3 minutes).

Add Egg and Vanilla

  • Beat in the egg and vanilla extract until fully incorporated.

Combine Wet and Dry

  • Gradually add the dry mixture to the butter mixture, mixing until just combined.

Portion Dough

  • Use a cookie scoop to portion dough into balls (about 1–1.5 tablespoons each) and place them 2 inches apart on the baking tray.

Top with Pineapple and Sugar

  • Gently flatten each dough ball and press a pineapple wedge onto the center of each cookie, then sprinkle with sugar.

Bake

  • Bake the cookies for 10–13 minutes or until the edges are lightly golden. Adjust baking time for preferred texture.

Cool and Finish

  • Allow the cookies to cool on the tray for 5 minutes before transferring to a cooling rack.

Notes

Store fully cooled cookies in an airtight container for 2–3 days. For longer freshness, refrigerate for up to 7 days.

Nutrition

Serving: 1gCalories: 150kcalCarbohydrates: 19gProtein: 1gFat: 7gSaturated Fat: 4gSodium: 100mgSugar: 8g
Keyword baking, Dessert Recipe, Pineapple Cookies, Seasonal, sugar cookies
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