Preheat your oven to 350°F and line a baking sheet with parchment paper.
In a stand mixer or large bowl with an electric mixer, beat the butter and sugars together. Then add in the vanilla extract and pumpkin and mix until everything is well combined and looking like a dreamy, pumpkin-y mixture.
Mix the dry ingredients - in another bowl, whisk together the gluten-free flour, baking soda, salt, and pumpkin pie spice.
Gradually add the dry ingredients to the wet ingredients, mixing just until combined. You don’t want to overmix here, or your cookies might end up tough.
Gently fold in the chocolate chips. Make sure every scoop of dough is packed with those melty little pieces of heaven.
Scoop large spoonfuls of dough onto the prepared baking sheet and bake for 11-15 minutes, or until the edges are golden brown and the centers are still slightly soft. Remember, they’ll continue to cook on the baking sheet after you take them out! You can make them smaller and more cookies if desired.
Let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely. Enjoy them warm with a glass of milk or with a hot cup of coffee.