Preheat oven to 350 degrees and line baking sheets with parchment paper.
In a medium bowl, whisk together flour, oats, pumpkin pie spice, cinnamon and salt.
In the bowl of a stand mixer, use paddle attachment to beat together butter and sugar, scraping down sides as needed. Add egg and vanilla extract and continue mixing until well combined.
Add flour mixture to mixer followed by pumpkin. Finally, stir in milk chocolate chips.
Use a medium cookie scoop to scoop cookie dough onto baking sheet. Top each cookie dough with additional chocolate chips.