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Spread pumpkin onto a plate in an even layer. Press with paper towels to absorb excess moisture. Repeat 3 times with clean paper towels.
In a medium bowl, whisk flour, baking soda, salt, and 1 tsp. cinnamon.
In a large bowl, using a handheld mixer on medium speed, beat butter, brown sugar, and ¼ c. granulated sugar until creamy. Add egg yolks and beat until combined. Add pumpkin and vanilla and beat until incorporated. Add dry ingredients and beat on medium-low speed until just combined.
Using a large cookie scoop (about 3 Tbsp.), scoop dough onto a parchment-lined baking sheet, spacing 2" apart. Refrigerate until cold, about 30 minutes.
Preheat oven to 350°. In a small bowl, mix remaining ¼ c. sugar and 1 tsp. cinnamon. Roll dough in sugar mixture and return to baking sheet.
Bake cookies until edges are just set and centers are still soft, 12 to 14 minutes. Let cool 5 minutes on baking sheet, then transfer to a wire rack and let cool completely.