Whisk melted butter, brown sugar, and ½ cup granulated sugar until smooth. Whisk in vanilla and pumpkin. Set aside.
In a large bowl, toss flour, salt, baking powder, baking soda, 1½ tsp cinnamon, and pumpkin pie spice together. Stir wet ingredients into dry until combined. Fold in cinnamon chips. Cover and chill at least 30 minutes (mandatory).
Preheat oven to 350°F. Line two baking sheets with parchment.
Mix remaining ½ cup granulated sugar and ½ tsp cinnamon in a bowl. Roll dough into 1.5-tbsp balls, coat generously in cinnamon sugar, and place on baking sheets. Slightly flatten each ball.
Bake 8–10 minutes — cookies will look soft and underbaked. Remove from oven. Press extra cinnamon chips on top if desired. Cool on sheets at least 10 minutes before transferring to a rack.