Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent the cookies from sticking and to make cleanup easier.

In a medium bowl, add the softened unsalted butter, white sugar, and light brown sugar. Beat the mixture with a mixer on medium speed until it becomes light and fluffy, which should take about 2-3 minutes. I like to make sure the butter is truly room temperature so it combines smoothly with the sugars.

Add the pumpkin puree and vanilla extract to the butter-sugar mixture. Beat until the pumpkin and vanilla are thoroughly mixed and the batter looks creamy.

Add the all-purpose flour, baking soda, baking powder, salt, pumpkin pie spice blend, and ground cinnamon to the wet ingredients. Beat just until all the dry ingredients are incorporated and the dough looks soft but scoopable. Be careful not to overmix to keep the cookies tender.

Using a spatula or spoon, gently fold the chocolate chips into the cookie dough until just combined. Avoid overmixing at this stage. For extra chocolate flavor, I sometimes press a few extra chips on top of each scoop before baking.

Using an ice cream or cookie scoop, portion the dough onto the prepared baking sheets, leaving about 2 inches of space between each cookie. For large cookies, use about 1/4 cup of dough per scoop; for smaller cookies, use about 1.5 tablespoons. If desired, press additional chocolate chips on top of each mound. Bake large cookies for 13-15 minutes and small cookies for 10-12 minutes, until the edges are just set. Allow the cookies to rest on the baking sheet for about two minutes before transferring them to a wire rack to cool.