Print
clock clock iconcutlery cutlery iconflag flag iconfolder folder iconinstagram instagram iconpinterest pinterest iconfacebook facebook iconprint print iconsquares squares iconheart heart iconheart solid heart solid icon

Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4 from 13 reviews
  • Author: Sue
  • Prep Time: 15 minutes
  • Cook Time: 13 minutes
  • Total Time: 28 minutes
  • Yield: 24 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

These Pineapple Upside Down Sugar Cookies combine the tropical sweetness of pineapple with classic buttery sugar cookies, creating a delightful treat that’s soft, flavorful, and topped with caramelized pineapple rings. Perfect for summer gatherings or anytime you crave a fruity twist on a traditional cookie.


Ingredients

Cookie Dough

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt

Topping

  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling


Instructions

  1. Preheat Oven: Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper to prevent sticking and ensure easy cleanup.
  2. Cream Butter and Sugar: In a large bowl, cream the softened unsalted butter and granulated sugar together until the mixture is light and fluffy, about 2-3 minutes. This step helps incorporate air into the dough for a tender texture.
  3. Add Egg and Vanilla: Beat in the large egg and vanilla extract (if using) until well combined, creating a smooth batter base for the cookies.
  4. Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening agents and seasoning.
  5. Combine Wet and Dry: Gradually add the dry ingredients to the wet mixture, mixing gently until a soft, cohesive dough forms without overworking to keep the cookies tender.
  6. Form Cookie Mounds: Using a spoon or cookie scoop, scoop out about 2 tablespoons of dough per cookie and place them spaced apart on the prepared baking trays.
  7. Add Pineapple Rings: Gently press one well-drained canned pineapple ring into the top of each dough mound, slightly flattening the dough underneath for an even surface.
  8. Sprinkle Sugar: Generously sprinkle the additional 2 tablespoons of sugar over the pineapple rings to create a sweet, caramelized crust during baking.
  9. Bake Cookies: Bake in the preheated oven for 11-13 minutes or until cookie edges are golden and centers are set, ensuring they are perfectly baked without over-drying.
  10. Cool Cookies: Allow the cookies to cool on the baking tray for a few minutes before transferring them to a wire rack to cool completely, preserving their texture and flavor.

Notes

  • Ensure the canned pineapple rings are well-drained to prevent excess moisture from making the cookies soggy.
  • You can substitute the all-purpose flour with a gluten-free blend to make these cookies gluten-free.
  • For a more pronounced vanilla flavor, do not omit the vanilla extract.
  • Store cookies in an airtight container at room temperature for up to 3 days to maintain freshness.
  • For a softer cookie, slightly reduce the baking time.