This copycat homemade Oatmeal Cream Pies recipe brings back the best childhood memories of biting into an ultra-chewy cookie with a rich creamy filling. They're surprisingly easy and satisfying to make from scratch!
In a medium bowl, whisk together the flour, salt, baking powder, baking soda, and cinnamon. Set aside.
In the bowl of a stand mixer fitted with the paddle attachment, beat the butter, granulated sugar, and brown sugar on medium-high speed until light and fluffy, about 2 to 3 minutes. Beat in the eggs, egg yolk, and vanilla, one at a time, beating well after each addition. Slowly beat in the flour mixture until just combined. Stir in the oats with a rubber spatula.
Using a spoon or large spring-loaded scoop, drop 3-tablespoon sized balls of dough onto prepared baking sheets. Flatten slightly with the bottom of a measuring cup.
Bake for about 12 to 14 minutes, or until the edges are slightly browned, rotating baking sheets halfway through. Let the cookies cool on baking sheets for 5 minutes before removing to wire racks to cool completely. Cookies can be stored in an airtight container at room temperature for up to 3 days.
Make the filling:
Mix all ingredients together with an electric mixer on low until combined, then beat on medium-high speed until light, fluffy, and smooth, about 5 minutes.
Spread or pipe the filling on half of your cookies and use the remaining cookies to sandwich. Serve or store in an airtight container in the fridge for up to 3 days. Let come to room temperature before serving.