Preheat the oven to 350°F (180°C). Cover a large baking sheet with parchment paper, then lightly coat the parchment with cooking oil spray to help prevent sticking. Set the prepared baking sheet aside.

Place the almond flour, 1/3 cup coconut sugar, and pumpkin pie spice in a large mixing bowl. Stir thoroughly until the sugar and spices are evenly dispersed throughout the almond flour.

Add the pumpkin puree, cooled melted coconut oil, and vanilla extract, if using. Mix with a spatula until a thick, moist, uniform dough forms. The mixture should remain slightly wet without becoming runny.

Allow the dough to rest for about 1 minute so the almond flour can absorb some of the moisture.

In a separate small bowl, combine the remaining 2 tablespoons coconut sugar with the ground cinnamon. Stir until evenly blended, then set the cinnamon sugar mixture aside.

Portion approximately 2 tablespoons of dough for each cookie. Lightly oil your hands and gently roll each portion into a ball.

Roll every dough ball in the cinnamon sugar mixture until the surface is fully coated. Arrange the coated portions on the prepared baking sheet, leaving approximately a thumb-width of space between them.

Use a finger to gently press each dough ball down slightly, creating a lightly flattened cookie shape.

Bake at 350°F (180°C) for 13–15 minutes, or until the tops develop a golden-brown appearance.

Remove the baking sheet from the oven and allow the cookies to cool on the pan for 5 minutes. Transfer them carefully to a wire cooling rack and leave them until completely cooled.