Place the pumpkin puree in a bowl lined with paper towels. Cover with another paper towel and gently press to remove excess moisture. Continue blotting until you have approximately 3/4 cup (170g) of thick pumpkin puree.
Preheat the oven to 350°F (177°C). Line large baking sheets with parchment paper or silicone baking mats.
Whisk together the rolled oats, flour, baking soda, salt, cinnamon, and pumpkin pie spice in a medium bowl.
In a separate large mixing bowl, beat the softened butter, granulated sugar, and brown sugar on medium-high speed for about 3 minutes, until creamy and well combined.
Beat in the egg yolk and vanilla. Add the blotted pumpkin puree and continue mixing until evenly incorporated.
Add the dry ingredients to the pumpkin mixture. Mix on low speed initially, then increase to medium just until combined. The finished dough should be soft, creamy, and slightly sticky.
Scoop scant 1 1/2-tablespoon portions of dough, approximately 25–30g each, onto the prepared baking sheets. Leave about 3 inches between cookies. Gently flatten each mound with the back of a spoon.
Bake for 14–16 minutes, or until the edges are set and lightly golden. Allow the cookies to rest on the baking sheet for 10 minutes before transferring them to a wire rack. Cool completely.
For the filling, beat the softened cream cheese and butter until smooth and creamy. Add the confectioners’ sugar, vanilla, pumpkin pie spice, and a pinch of salt. Begin mixing on low, then beat on high until light and smooth.
Spread or pipe the cream cheese filling onto the flat side of half the cookies. Top each with another cookie and gently press together. Your Pumpkin Oatmeal Cream Pies are ready to serve.
Notes
Pure pumpkin puree works best for this recipe. Avoid pumpkin pie filling because it contains additional sweeteners and spices that can alter the flavor and texture.