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Preheat the oven to 350°F. Line two half-sheet trays with parchment paper.
In a large mixing bowl, beat the butter with a rubber spatula to loosen it up, then beat in the sugar, cinnamon, pumpkin pie spice (if using), salt, baking soda and baking powder.
Add the vanilla and puréed pumpkin to the bowl and whisk until combined.
Using the rubber spatula, fold in the flour until just a few streaks of white remain, then fold in the chocolate chips just until evenly incorporated.
Dole out eight dough balls per tray, about 3 tablespoons each, in a staggered formation.
Top each dough ball with 4 or 5 of the remaining chocolate chips, if desired.
Bake, one tray at a time, for 13 or 14 minutes, until they look just dry on the tops.
Allow to cool on the tray for 5 to 10 minutes then carefully transfer to a wire rack to cool completely.