Preheat oven to 350 degrees F. Line a large baking sheet with parchment paper or a Silpat baking mat and set aside.
In a medium bowl, whisk together the flour, baking soda, cinnamon, salt, ginger, nutmeg, and cloves. Set aside.
In the bowl of a stand mixer or with a hand mixer, beat the butter and sugars together until creamy and smooth, scraping down the sides of the bowl with a spatula as necessary.
Place a couple of paper towels on a plate or in a bowl. Place the pumpkin puree in the center of the paper towels. Use another paper towel to blot the pumpkin, 5 or 6 times to soak up some of the moisture.
Add the blotted pumpkin, egg yolk, and vanilla to the mixing bowl. Beat until well combined.
With the mixer on low, beat in the dry ingredients until just combined. Don’t over mix. Stir in the oats and chocolate chips.
Use a cookie scoop to drop the dough onto the prepared baking sheet, about 1.5 tablespoons of dough per cookie, leaving about 2 inches of space in between because the cookies will spread.
Bake for 12 to 14 minutes or until cookies are set around the edges but still soft in the center. Remove from oven and sprinkle with flaky sea salt, if desire. Let the cookies cool for 5 minutes on the baking sheet. Transfer to a wire cooling rack and cool completely.