Preheat oven to 350 degrees. Line a baking sheet with parchment paper.
In a large bowl, add in the butter and brown sugar. Beat with a hand mixer on medium until light and fluffy, about 1 to 2 minutes.
Add in the vanilla extract, eggs, and pumpkin puree. Beat until the eggs are incorporated.
In a separate bowl, add in the dry vanilla pudding mix, flour, pumpkin spice, baking soda, and salt. Whisk to combine.
Pour the dry ingredients in with the wet and beat on medium until the flour is just incorporated.
Add in the chocolate chips and stir until evenly distributed.
Using a 1 ½ tablespoon cookie scoop, scoop cookie dough and place them 2 inches apart on the prepared baking sheet.
Place in the preheated oven and bake for 12 to 14 minutes until the edges are set.
Let cool for 5 minutes and transfer to a wire rack or paper towel to cool completely.
Notes
Wrap the inside of a small bowl with paper towels and place the cup of pumpkin puree on top of the paper towels. Using another paper towel, pat the pumpkin puree.