Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper. Measure 1/2 cup pumpkin puree and place it in the center of 3 layers of paper towels, a clean dish towel, or a fine-mesh strainer. Gently press and squeeze to remove excess moisture - you'll end up with about 1/3 cup of thick pumpkin paste. This step is crucial for chewy cookies instead of cakey ones.
In a large bowl, cream together 1/2 cup room temperature butter, 1/3 cup strained pumpkin puree, and 2/3 cup cane sugar until light and fluffy. Add 2 egg yolks and 1 teaspoon vanilla extract, mixing until well combined.
To the same bowl, add 1-1/2 cups almond flour, 1/3 cup gluten-free flour, 1/2 teaspoon baking soda, 1 teaspoon cream of tartar, 1/2 teaspoon salt, 1/2 teaspoon cinnamon, and 1/2 teaspoon pumpkin pie spice and mix just until combined. The dough will be soft and slightly sticky.
In a small bowl, mix together 1/4 cup turbinado sugar and 1/2 teaspoon cinnamon. If you're not rolling the cookies in sugar, place the dough bowl in the freezer for 20 minutes to firm up the butter for easier scooping.
Using a medium cookie scoop or spoon, scoop portions of dough and drop them into the cinnamon-sugar mixture. Toss to coat all sides and place on your prepared baking sheet, spacing them 2 inches apart. Bake for 9-12 minutes, or until lightly golden on top. The centers should still look slightly soft.
Allow the cookies to cool on the baking sheet for 5 minutes so the butter can solidify slightly and they hold their shape. Then transfer to a wire rack to cool completely.