Preheat your oven to 350 degrees F and line two large baking sheets with parchment paper or silicone baking mats. Set aside.
In a medium bowl, whisk together the flour, pumpkin pie spice, baking soda and salt until combined. Set aside.
In a stand mixer, with paddle attachment fixed, mix the coconut oil, brown sugar and granulated sugar until smooth. Add the egg, pumpkin puree and milk. Mix again to combine. Add the vanilla extract and mix again.
With mixer set on low, gradually add the dry ingredients to the wet. Mix until just moistened. Do not overmix. Fold in the chocolate chips.
In 2 tablespoon-sized portions, drop the dough onto the prepared baking sheets. Make sure there are at least 2-3 inches between each cookie. They will spread.
Bake the cookies for 10-12 minutes or until the cookies are brown and starting to crisp.
Remove from oven and allow to cool for 15 minutes on the baking sheets. Transfer to a wire rack to cool the rest of the way.
Store in an airtight container for about a week. Enjoy!