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Pineapple Cookies

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  • Prep Time: 30 minutes
  • Cook Time: 12 minutes
  • Total Time: 2 hours 42 minutes
  • Yield: 36 cookies 1x
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

These delightful Pineapple Cookies feature a soft cream cheese and pineapple filling wrapped in tender almond-scented cookie dough, rolled and sliced for a stunning pinwheel effect. Finished with a sweet pineapple glaze and optional sprinkles, they’re perfect for holidays or tropical-themed gatherings.


Ingredients

Scale
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 3/4 tsp almond extract
  • 1 egg, room temperature
  • 2 1/2 cups all-purpose flour
  • 1/4 tsp salt
  • 20 oz crushed pineapple, well drained (juice reserved)
  • 8 oz cream cheese, softened
  • 1/3 cup granulated sugar
  • 1 cup powdered sugar
  • 2 tbsp pineapple juice
  • Sprinkles (optional)

Instructions

  1. Drain crushed pineapple thoroughly, reserving the juice for the glaze. Press out as much liquid as possible.
  2. In a medium bowl, beat cream cheese and 1/3 cup sugar until fluffy and smooth (about 2 minutes).
  3. Stir in the drained pineapple until combined. Reserve 1/2 cup of filling for serving with crackers and set aside the remaining filling.
  4. In a large mixing bowl, cream butter and 1 cup sugar until smooth.
  5. Mix in almond extract and egg until well combined.
  6. Stir in flour and salt just until the dough is incorporated. Do not overmix.
  7. Divide dough in half. Using plastic wrap, press half of the dough into an 8-inch square on a covered cutting board.
  8. Spread half of the pineapple filling evenly over the dough, leaving a 1/2-inch border.
  9. Carefully roll up the dough using the plastic wrap. Pinch edges to seal. Wrap tightly in plastic wrap and refrigerate for at least 2 hours or up to 48 hours. Repeat with remaining dough and filling.
  10. Preheat oven to 350°F (177°C) and line a baking sheet with parchment paper.
  11. Cut chilled rolls into 1/4 to 3/8-inch slices and place them on the prepared baking sheet.
  12. Bake for 10–12 minutes, or until the bottoms are lightly golden. Let cookies cool on the baking sheet for 1–2 minutes before transferring to a wire rack.
  13. Whisk together powdered sugar and reserved pineapple juice in a small bowl until smooth.
  14. Drizzle glaze over cooled cookies. Add sprinkles while glaze is wet if desired. Let glaze set before storing.

Notes

  • Ensure pineapple is well-drained to avoid soggy filling and dough.
  • Chilling the dough is essential for clean slices and maintaining shape during baking.
  • Cookies can be frozen before or after baking for longer storage.
  • Use reserved 1/2 cup filling as a dip for crackers or fruit.
  • Store glazed cookies in an airtight container for up to 5 days.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 120
  • Sugar: 10g
  • Sodium: 40mg
  • Fat: 6g
  • Saturated Fat: 4g
  • Unsaturated Fat: 1.5g
  • Trans Fat: 0g
  • Carbohydrates: 14g
  • Fiber: 0g
  • Protein: 1g
  • Cholesterol: 20mg