• 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.
• In a medium bowl, whisk together the flour, cinnamon, pumpkin pie spice, baking soda and salt. Set aside.
• 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.
• Add the egg yolk and vanilla. Mix until combined.
• Add the blotted pumpkin and mix again until smooth, scraping down the sides of the bowl as needed.
• 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.
• Add the chopped chocolate and mix on low for a few seconds, just until evenly distributed.
• Cover the dough and refrigerate for 30–45 minutes.
• Preheat the oven to 350°F. Line two baking sheets with parchment paper.
• Combine the granulated sugar and cinnamon in a shallow bowl.
• 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.
• Gently flatten each ball into a thick disc and press a few additional pieces of chopped chocolate into the top.
• Bake one sheet at a time for 12–14 minutes. The edges should look set, but the centers should still appear slightly soft.
• Sprinkle the cookies with flaky salt immediately after removing them from the oven.
• Allow the cookies to cool on the baking sheet for five minutes before transferring them to a wire rack.
• 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

• Don’t skip blotting the pumpkin. This is the key to achieving a chewy texture.
• The cookies will continue to bake and set on the hot baking sheet.
• For a perfectly round shape, use a large round cookie cutter or bowl to gently scoot the cookies into circles immediately after baking.
• The optional caramel drizzle and ice cream are not included in the nutrition estimate.