Preheat oven to 350F and line two large sheet pans with parchment paper. Set aside.
Place pumpkin puree in the middle of a kitchen towel. Gather up edges of kitchen towel and gently squeeze pumpkin over a sink or bowl until all the liquid is squeezed out. Set pumpkin aside.
Place butter and both sugars in the bowl of a large stand mixer, fitted with a paddle attachment OR in a large mixing bowl with a wooden spoon. Mix on medium speed or by hand until creamy, about 2 minutes. Add squeezed pumpkin puree, egg yolk, and vanilla, beating well until smooth.
In a separate medium bowl, combine flour, pumpkin pie spice, baking soda, and salt. Fold into butter mixture until dough is just combined, then fold in chocolate chips.
Use a medium cookie scoop to scoop dough out into 1-in balls. Place balls 2 inches apart on prepared baking sheets. Flatten dough balls slightly.
Bake cookies at 350F on middle rack 10-12 minutes until edges of cookies are lightly browned. Remove cookies from oven and allow to cool on baking sheet 10 minutes before transferring to a wire cooling rack to cool completely. Enjoy!