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Preheat oven to 350°F (177°C). Line baking sheets with parchment paper or silicone baking mats. Set aside.
Whisk the flour, baking soda, cinnamon, pumpkin pie spice, salt, and oats together in a large bowl. Set aside.
Whisk the melted butter, maple syrup, brown sugar, granulated sugar, egg yolk, blotted pumpkin, and vanilla extract together until combined. Pour into dry ingredients and mix everything together until completely combined. Fold in the chocolate chips.
Scoop cookie dough, about 1.5 Tablespoons of dough per cookie, and place 3 inches apart on the baking sheets. Flatten slightly. Bake for 13-14 minutes or until lightly browned on the sides. The centers will look very soft.
Remove from the oven and allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely. While the cookies are still warm, I like to press a few more chocolate chips into the tops—this is only for looks!