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Holiday Cookie Box Assortment

Holiday cookie box assortment brings sugar cookies, chocolate crinkles, and cranberry-pistachio shortbread together in one festive collection. The cookies are baked in batches and chilled dough helps create crisp-edged, tender cookies with distinct flavors and textures.
Prep Time 1 hour
Cook Time 40 minutes
chilling 2 hours 45 minutes
Total Time 4 hours 25 minutes
Servings: 12 servings
Course: Dessert
Cuisine: American
Calories: 760

Ingredients
  

For the cookie doughs
  • 5.5 cup all-purpose flour divided (2 1/4 cups for the sugar cookies, 1 cup for the chocolate crinkles, and 2 1/4 cups for the shortbread)
  • 1.5 tsp baking powder divided (1/2 teaspoon for the sugar cookies and 1 teaspoon for the chocolate crinkles)
  • 1 tsp fine salt divided (1/4 teaspoon for the sugar cookies, 1/4 teaspoon for the chocolate crinkles, and 1/2 teaspoon for the shortbread)
  • 1.5 cup unsalted butter softened and divided (1/2 cup for the sugar cookies and 1 cup for the shortbread)
  • 0.75 cup granulated sugar for the sugar cookies
  • 1 cup granulated sugar for the chocolate crinkle cookies
  • 0.67 cup granulated sugar for the shortbread
  • 3 eggs large (1 for the sugar cookies and 2 for the chocolate crinkles)
  • 2 tsp vanilla extract (1 teaspoon for the sugar cookies and 1 teaspoon for the chocolate crinkles)
For the sugar cookies
  • 2 tbsp sanding sugar
For the chocolate crinkle cookies
  • 0.25 cup vegetable oil
  • 0.5 cup unsweetened cocoa powder
  • 0.5 cup powdered sugar
For the cranberry-pistachio shortbread
  • 0.5 cup dried cranberries roughly chopped
  • 0.5 cup pistachios shelled, roughly chopped

Equipment

  • 2 18x13-inch rimmed baking sheets

Method
 

Make the sugar cookies
  1. Heat the oven to 350°F and line two 18x13-inch rimmed baking sheets with parchment paper.
  2. Whisk 2 1/4 cups flour, 1/2 teaspoon baking powder, and 1/4 teaspoon salt in a medium bowl.
  3. Beat 1/2 cup butter with 3/4 cup granulated sugar in a large bowl until light and fluffy, about 2 minutes.
  4. Beat in 1 egg and 1 teaspoon vanilla until combined.
  5. Mix the flour mixture into the butter mixture just until a soft dough forms.
  6. Roll the dough between two sheets of parchment to 1/4-inch thickness, then chill flat for 45 minutes.
  7. Cut out 2-inch cookies, rerolling scraps as needed, and place them on the prepared sheets.
  8. Sprinkle with the sanding sugar.
  9. Bake the cookies in batches at 350°F for 8–10 minutes, until the edges are set and just beginning to turn golden.
  10. Cool the cookies on the baking sheets for 5 minutes.
  11. Transfer them to a wire rack to cool completely.
  12. Let each sheet cool before loading another batch.
Make the chocolate crinkle cookies
  1. Stir 1 cup granulated sugar and the vegetable oil together in a large bowl.
  2. Beat in 2 eggs and 1 teaspoon vanilla until smooth.
  3. Whisk 1 cup flour, 1/2 cup cocoa powder, 1 teaspoon baking powder, and 1/4 teaspoon salt in a separate bowl.
  4. Stir the flour mixture into the egg mixture just until combined.
  5. Cover and chill the dough for 1 hour, until firm enough to scoop.
  6. Scoop the dough into 1-tablespoon portions.
  7. Roll each portion into a ball.
  8. Coat each ball generously in the powdered sugar.
  9. Bake in batches at 350°F for 10–12 minutes, until the tops are cracked and the edges are set; use a cool baking sheet for each batch.
  10. Cool on the baking sheets for 5 minutes.
  11. Transfer to a wire rack to cool completely.
Make the cranberry-pistachio shortbread
  1. Beat 1 cup butter with 2/3 cup granulated sugar in a large bowl until smooth and creamy, about 2 minutes.
  2. Mix in 2 1/4 cups flour and 1/2 teaspoon salt on low speed just until the dough starts to come together.
  3. Fold in the dried cranberries and pistachios until evenly distributed.
  4. Divide the dough in half.
  5. Shape each half into a 6-inch-long log about 2 inches in diameter.
  6. Wrap the logs and chill for 1 hour.
  7. Heat the oven to 325°F and line the baking sheets with fresh parchment paper.
  8. Slice each log into 12 rounds, each about 1/2 inch thick.
  9. Arrange the rounds on the baking sheets.
  10. Bake in batches at 325°F for 18–22 minutes, until the edges are lightly golden; use a cool baking sheet for each batch.
  11. Cool on the baking sheets for 10 minutes.
  12. Transfer to a wire rack to cool completely.
Pack the boxes
  1. Arrange 2 of each kind of completely cooled cookie in each of 12 cookie boxes.

Notes

For clean shortbread slices, chill the logs until firm. Store the cookies airtight at room temperature for up to 5 days; freeze baked cookies for up to 2 months. For a dairy-free swap, use plant-based butter sticks.