In a medium bowl, sift the flour, baking soda, cinnamon, pumpkin pie spice, and salt. Set aside.
2 cups All-purpose flour, 1 tsp Baking soda, 2 tsp Ground cinnamon, 1 tsp Pumpkin pie spice, 1 tsp Salt
Spread the pumpkin puree on a dinner plate. Use 8 sheets of paper towels ( 2 at a time) and press on the pumpkin to soak up the moisture.
3/4 cup Pumpkin puree
In a large bowl using a mixer, beat the butter and sugar on high speed for 2 minutes. It will become fluffy and pale in color.
1 cup Unsalted butter, 1 1/2 cup White granulated sugar
Add in the vanilla, pumpkin puree, and egg yolk. Mix on medium speed until combined.
1 tsp Pure vanilla extract, 1 Egg yolk
Add in the flour mixture and mix on low speed until just combined.
Preheat the oven to 350℉. Line two cookie sheets with parchment paper. Let the cookie dough rest for 10 minutes to prevent spreading.
Use a large cookie scoop (3 Tablespoons) to scoop the cookie dough balls. Place 6 cookie dough balls per cookie sheet.
Take the crumble out of the fridge and use a fork to first break up the largest pieces. Then, use your hands to break up the crumbles into small pieces.
Use a small handful and press the crumble to the top of the cookie dough balls.
Bake for 13-15 minutes. Bake until the edges look set.
Let the cookies sit on the hot pan for 5 minutes before transferring to a cooling rack. Cool completely before icing.