Preheat the oven to 350°F (175°C).
In a medium mixing bowl, add the butter and both sugars. Cream together with an electric mixer until well combined.
Add in the pumpkin puree and vanilla extract, and beat together until smooth.
In a separate bowl, whisk together the gluten-free flour, baking soda, pumpkin pie spice, cinnamon, and salt.
Gradually add the dry ingredients to the wet mixture, beating until a dough forms.
Fold in the chocolate chips.
Line a baking sheet with parchment paper. Scoop heaping 2-tablespoon portions of dough onto the sheet, spacing them a few inches apart. You can make the cookies smaller if you prefer.
Bake for 13-18 minutes, or until the edges are slightly golden brown and the centers are matte. The cookies will firm up as they cool, so if you prefer them soft and gooey, avoid over-baking.
Sprinkle a few extra chocolate chips on top of the cookies as soon as they come out of the oven.
If the cookies didn’t spread as much as desired, gently tap the cookie tray on the oven rack a few times to encourage spreading.
Let the cookies cool on the baking sheet for at least 30 minutes before enjoying.