Line a medium sized bowl with a 2 layers of paper towels. Measure out 1 cup (260 g) pumpkin puree onto the paper towels. Allow the pumpkin puree to sit on the paper towels for about 5 - 10 minutes. Gather the paper towels and gently squeeze out the excess moisture. Some moisture will still remain in the pumpkin puree. The puree should reduce down to about ¾ cup (195 g).
1 cup (260 g) canned pumpkin puree
In another mixing bowl whisk together the flour, oats, baking soda, ground cinnamon, pumpkin spice and salt until well combined. Set aside for now.
2 cups (240 g) all purpose flour, 1 cup (80 g) quick cooking or old fashioned oats, 2 teaspoons ground cinnamon , 2 teaspoons pumpkin spice, 1 teaspoon baking soda, ½ teaspoon salt
In a microwave safe bowl heat slices of cold from the fridge butter for 30 seconds. The butter should be mostly solid with softened edges. Transfer the softened butter into a large mixing bowl fitted with a paddle attachment. Add the light brown sugar and granulated sugar. Mix the butter and sugars on medium speed for 2 - 3 minutes or until the butter and sugars are well combined. ¾ cup (170 g) unsalted butter, cold and sliced, ¾ cup (150 g) light brown sugar, ½ cup (100 g) granulated sugar, 1 large egg yolk , 2 tablespoons (30 ml) molasses , 2 teaspoons (10 ml) vanilla extract
On low, cream in the blotted pumpkin puree, egg yolk and vanilla extract until smooth and well combined. With the mixer on low, add the dry ingredients into the wet a little at a time. Mix until just combined. Cover the cookie dough and transfer to the fridge to chill for 30 minutes - 2 hours. The longer the chill, the chewier and softer the cookie. Preheat the oven to 350 F (177 C) for about 30 minutes before baking the cookies. Line a large baking sheet with parchment paper. Using a medium cookie scoop (2 tablespoons, 30 ml), scoop the oatmeal and pumpkin cookie dough into balls and place them onto the lined baking sheet about 3 inches (8 cm) apart.
Bake the oat pumpkin cookies at 350 F (177 C) for 10 - 12 minutes or until the edges of the cookies are set and are a light golden brown. The center of the cookies will be slightly puffed up. Remove the cookies from the oven.
Reshape any cookies using a biscuit or cookie cutter slightly wider than the cookie. Place the cutter over the cookies so the edges of the cookie are inside the cookie/ biscuit cutter. In a circular motion, gently nudge the edges back into a round shape. Cool the chewy oatmeal and pumpkin cookies on the baking sheet for 10 minutes. Then transfer to a cooling rack to cool completely to room temperature. In another bowl whisk the powdered sugar, pumpkin spice or cinnamon, vanilla extract and milk together until smooth and well combined. Dip the top of each cooled pumpkin oatmeal cookie into the glaze. Gently shake the excess glaze off the top of the cookie and return the the iced pumpkin oatmeal cookie onto the cooling rack to set. Repeat with all remaining cookies. Allow the icing to set for about 30 minutes and enjoy. 1½ cup (180 g) powdered sugar, 1 teaspoon vanilla extract , ½ teaspoon ground cinnamon or pumpkin spice, 2 - 3 tablespoons (30 - 45 ml) milk, as needed