Chewy Pumpkin Chocolate Chunk Cookies

1 Place the pumpkin purée between several layers of paper towels. Press firmly to remove as much moisture as possible. The pumpkin should reduce to approximately ¼ cup and have a thick, paste-like consistency.
2 In a medium bowl, whisk together the flour, cinnamon, pumpkin pie spice, baking soda and salt. Set aside.
3 Add the softened butter, brown sugar and granulated sugar to the bowl of a stand mixer fitted with the paddle attachment. Beat on medium speed for two to three minutes, or until light and creamy.
4 Add the egg yolk and vanilla. Mix until combined.
5 Add the blotted pumpkin and mix again until smooth, scraping down the sides of the bowl as needed.
6 Turn the mixer to its lowest speed and gradually add the dry ingredients. Mix only until a soft dough forms and no streaks of flour remain.
7 Add the chopped chocolate and mix on low for a few seconds, just until evenly distributed.
8 Cover the dough and refrigerate for 30–45 minutes.
9 Preheat the oven to 350°F. Line two baking sheets with parchment paper.
10 Combine the granulated sugar and cinnamon in a shallow bowl.
11 Portion the dough into approximately ¼-cup-sized balls. Roll each portion in the cinnamon sugar and arrange them on the prepared baking sheets, leaving plenty of room between each cookie.
12 Gently flatten each ball into a thick disc and press a few additional pieces of chopped chocolate into the top.
13 Bake one sheet at a time for 12–14 minutes. The edges should look set, but the centers should still appear slightly soft.
14 Sprinkle the cookies with flaky salt immediately after removing them from the oven.
15 Allow the cookies to cool on the baking sheet for five minutes before transferring them to a wire rack.
16 If making the optional drizzle, stir together the caramel sauce, maple syrup and flaky salt. Drizzle lightly over warm cookies or serve alongside vanilla ice cream.
Notes
18 Don’t skip blotting the pumpkin. This is the key to achieving a chewy texture.
19 The cookies will continue to bake and set on the hot baking sheet.
20 For a perfectly round shape, use a large round cookie cutter or bowl to gently scoot the cookies into circles immediately after baking.
21 The optional caramel drizzle and ice cream are not included in the nutrition estimate.