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Pumpkin Swirl Cookies

Break open these oversized cookies, fragrant with pumpkin and spice, to reveal a soft interior with a beautiful swirl.
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  • Level: Easy
  • Total: 4 hr 20 min (includes chilling and cooling times)
  • Active: 55 min
  • Yield: 12 large cookies
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Ingredients

Sugar Cookie Dough:

2 1/2 cups all-purpose flour (see Cook's Note)

1 1/2 teaspoons baking powder 

1/2 teaspoon kosher salt 

1 1/2 cups granulated sugar 

2 sticks unsalted butter, at room temperature 

1 large egg, at room temperature 

1 teaspoon pure vanilla extract 

Pumpkin Cookie Dough:

2 1/2 cups all-purpose flour, plus additional for dusting (see Cook's Note)

2 teaspoons pumpkin pie spice 

1 teaspoon ground cinnamon 

1 teaspoon baking soda 

1/2 teaspoon kosher salt 

1 1/4 cups packed dark brown sugar 

1 1/2 sticks (12 tablespoons) unsalted butter, at room temperature 

1 large egg, at room temperature 

1/2 cup pumpkin puree 

1 teaspoon pure vanilla extract 

Glaze:

2 cups confectioners' sugar

1 teaspoon pumpkin pie spice 

1/4 cup milk 

Directions

  1. For the sugar cookie dough: Whisk together the flour, baking powder and salt in a medium bowl; set aside.
  2. Beat together the granulated sugar and butter in a stand mixer fitted with the paddle attachment, scraping down the bowl and paddle once, until light and fluffy, about 3 minutes. Add the egg and beat to fully combine. Add the vanilla and beat to combine. Turn off the mixer. Add half of the dry ingredients and turn the mixer to low; beat until incorporated. Scrape down the bowl and paddle, add the remaining dry ingredients and beat on low until just incorporated. Scrape down the bowl and increase the mixer speed to medium low for 1 minute to make sure the dough is well combined.  
  3. Transfer the dough to a piece of plastic wrap. Use a rubber spatula to spread and press the dough into a flat rectangle. Add a second piece of plastic wrap on top, and flatten the rectangle using a rolling pin to approximately 8 by 10 inches. Wrap tightly and refrigerate at least 2 hours and up to overnight.  
  4. For the pumpkin cookie dough: Whisk together the flour, pumpkin pie spice, cinnamon, baking soda and salt in a medium bowl; set aside. 
  5. Beat together the brown sugar and butter in a stand mixer fitted with the paddle attachment, scraping down the bowl and paddle once, until light and fluffy, about 3 minutes. Add the egg and beat to fully combine. Add the pumpkin and vanilla and beat to combine. Turn off the mixer. Add half the dry ingredients and beat on low speed until incorporated. Scrape down the bowl and paddle, then add the remaining dry ingredients and beat on low speed until just incorporated. Scrape down the bowl and beat on medium low for 1 minute to make sure the dough is well combined.  
  6. Transfer the dough to a piece of plastic wrap. Use a rubber spatula to spread and press the dough into a flat rectangle. Add a second piece of plastic wrap on top and flatten with a rolling pin to approximately 8 inches by 10 inches. Wrap tightly and refrigerate at least 2 hours and up to overnight. 
  7. Preheat the oven to 350 degrees F and line 2 baking sheets with parchment. 
  8. Unwrap the pumpkin cookie dough and place on a lightly floured piece of parchment. Lightly flour the top and a rolling pin and roll into a larger rectangle about 10 1/2 by 16 inches (see Cook's Note). Slide the parchment with the dough onto a baking sheet and refrigerate while you repeat the process with the sugar cookie dough. Roll and refrigerate the sugar cookie dough in the same manner. 
  9. Use a pastry brush to dust off any excess flour from the top of the pumpkin cookie dough. Using the parchment to help you, flip the pumpkin cookie dough onto the sugar cookie dough, lining up the 2 rectangles as closely as possible. Cut the dough in half crosswise with a very sharp knife or pastry cutter so you now have 2 rectangles that are 10 1/2 by 7 inches. Stack the dough rectangles on top of one another so you now have 4 layers of alternating cookie dough. Cut this stack crosswise into 6 rows, then lengthwise into 4 rows so you end up with a total of 24 squares. Stack one layered square on top of a second one and, using lightly floured hands, gently press the edges together and round into a domed ball. Place on the prepared baking sheet. Repeat with the remaining squares, evenly spacing 6 dough balls on each lined baking sheet.   
  10. Bake, rotating the baking sheets halfway through, until the cookies are puffed in the center and golden brown around the edges, 25 to 30 minutes. Let cool on the pans 10 minutes, then transfer to a wire rack set inside a baking sheet to cool completely.  
  11. For the glaze: Meanwhile, whisk together the confectioners' sugar with the pumpkin pie spice in a medium bowl. Add the milk and whisk until completely incorporated. Transfer to a quart-sized resealable plastic bag or piping bag. Snip the end and drizzle the cooled cookies with the icing. Let set, about 20 minutes.

Cook’s Note

When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.) The pumpkin dough will be much softer than the sugar cookie dough so you will have to use more flour when rolling out to prevent sticking. Work quickly; if the dough gets too soft or warm, place the whole piece of parchment on a sheet pan and place in the freezer for a few minutes.