Place two paper towels inside a medium bowl and spoon the pumpkin puree on top. Press additional paper towels over the pumpkin to remove as much excess moisture as possible. You should have approximately 3/4 cup (170g) of pumpkin remaining.

Preheat the oven to 350°F (177°C). Line large baking sheets with parchment paper or silicone baking mats.

In a medium bowl, whisk together the rolled oats, flour, baking soda, salt, cinnamon, and pumpkin pie spice.

In a separate large mixing bowl, beat the softened butter, granulated sugar, and brown sugar with an electric mixer for about 3 minutes, until light and creamy.

Add the egg yolk and vanilla. Beat until completely incorporated.

Add the blotted pumpkin and mix again until combined.

Gradually add the dry ingredients to the pumpkin mixture. Mix on low speed initially, then increase to medium speed just until everything is incorporated. The finished cookie dough should be soft, creamy, and slightly sticky.

Scoop portions of dough measuring roughly 1 1/2 tablespoons each onto the prepared baking sheets, leaving approximately 3 inches between them. Gently flatten each portion with the back of a spoon.

Bake for 14–16 minutes, until the edges are set and lightly browned. Cool on the baking sheets for about 10 minutes before transferring the cookies to a wire rack.

Allow the cookies to cool completely before assembling the Pumpkin Oatmeal Cream Pies.

For the filling, beat the softened cream cheese and butter together until smooth and creamy.

Add the confectioners’ sugar, vanilla, pumpkin pie spice, and a pinch of salt. Begin mixing on low speed, then increase to high and beat until fluffy and smooth.

Pipe or spread the cream cheese filling over the flat side of half the cooled cookies.

Place another cookie on top of each filled cookie and press very gently to create sandwich cookies.