Preheat the oven to 350 degrees F. Line a cookie sheet with parchment paper.
Add pumpkin puree, light brown sugar, coconut oil, and vanilla extract to a medium mixing bowl. Mix together using a large spoon or hand/stand mixer on low.
Once combined, add ½ cup flour, pumpkin pie spice, baking soda, and salt. Stir to combine. Stir in the remaining flour ½ cup at a time to avoid a crumbly mixture.
Continue mixing until a large uniform ball of cookie dough forms. The dough should be soft but not sticky. You should be able to roll it into a round ball.
Fold in the chocolate chips.
Measure out 18 cookies, each about 1.5-2 tablespoons in size. Use your hands to roll each cookie dough scoop into a ball. The ball should be about the size of a ping-pong ball.
Place cookies 2 inches apart on the cookie sheet. You may need to bake in 2 batches. Lightly press each cookie with the palm of your hand to flatten into a puck shape.
Place the cookie sheet on the middle rack of the oven. Bake for 9-11 minutes at 350 degrees. The cookies are ready when firm at the edges and cooked but still soft on top. Remove from oven and let rest for 5 minutes before transferring to a cooling rack to cool.
Keep at room temperature for up to 3 days or freeze for up to 3 months. Enjoy!
Video
Notes
Coconut oil: To melt coconut oil, microwave it in 15-second intervals or heat on the stove over medium heat until melted.
I recommend using an oven thermometer. Oven temperatures can vary widely and the only way to know if your oven is the temperature it says it is is to use an oven thermometer.
For the most consistent results, use the "spoon and level" method for measuring out flour. Simply use a spoon to add flour to your cup measure until overflowing, then use the back of a knife to level off the excess flour.