Preheat the oven to 350 degrees F. Line a baking sheet with parchment paper and set aside.
Line a medium-sized bowl with paper towels. Add the pumpkin puree to the lined bowl. Using the paper towels, squeeze a bit of the moisture out of the canned pumpkin. Check out Sally's blog for a visual. Removing some of the moisture from the pumpkin helps produce a less cake-like cookie. Which is what we're going for here.
In another medium-sized bowl, whisk the flour, baking soda, spices, salt, and oats together. Set this aside.
In yet another medium-sized bowl, whisk the melted butter, maple syrup, sugars, egg yolk, pumpkin, and vanilla extract together.
Pour the wet ingredients into the dry ingredients and mix until combined. Fold in the chocolate chips.
Using a cookie scoop, scoop ~1.5 tbs-sized balls of dough onto the prepared baking sheets. Smoosh the dough balls down slightly with your fingers. They don't spread much on their own, so they need some help in this department. Bake for 12-13 minutes, or until lightly browned on the edges.
Remove the baking sheets from the oven. Press a few chocolate chips into the tops of the cookies while they are still warm. Allow the cookies to cool for 5 minutes on the baking sheets before removing them to a wire rack to finish cooling completely.