In a small bowl, whisk together the softened cream cheese, sugar, and vanilla extract until smooth.
Line a small tray or plate with parchment paper. Divide the cream cheese mixture into 6–8 portions and scoop onto the parchment. Freeze for about 30 minutes, or until firm enough to handle.
In a large bowl, whisk together the melted, slightly cooled butter, brown sugar, and granulated sugar until well combined. Add the pumpkin puree, egg, and vanilla extract and whisk until smooth.
In a separate bowl, whisk together the flour, baking soda, salt, pumpkin pie spice, and cinnamon.
Gradually fold the dry ingredients into the wet ingredients until just combined. Avoid overmixing.
In a small bowl, mix together the granulated sugar, cinnamon, and pumpkin pie spice.
Scoop about cookie dough (mine is around 2.5 tbsp) into your hand and gently flatten it. Place one frozen cream cheese portion in the center, then carefully wrap the dough around it, making sure the filling is completely sealed.
Roll each stuffed cookie in the cinnamon-spiced sugar coating and place on a parchment-lined baking sheet, leaving space between each cookie.
Bake at 350°F for 14–16 minutes, or until the edges are set and the centers still look slightly soft.
Let the cookies cool on the baking sheet for about 10 minutes before transferring them to a cooling rack.
Enjoy!