Soft and chewy Oatmeal Cream Pies made with old-fashioned oats, brown sugar, and cinnamon, filled with sweet vanilla buttercream. Better than Little Debbie!
Preheat the oven to 350°F and line large baking sheets with parchment paper.
In a small bowl, whisk together the 1 ½ cups flour, 1 teaspoon baking soda, 1 teaspoon cinnamon, and ½ teaspoon salt. Set aside.
In the bowl of a stand mixer fitted with the paddle attachment, beat the 1 cup butter, ¾ cup brown sugar, and ½ cup granulated sugar together on medium-high speed until light and fluffy, about 3-4 minutes.
Add the 2 eggs and 1 teaspoon vanilla extract, mixing on medium speed until fully combined and smooth.
With the mixer on low speed, gradually add the flour mixture to the butter mixture until just combined. Add the 3 cups oats and mix on low until evenly distributed throughout the dough.
Using a large cookie scoop (about 2 tablespoons), scoop dough and place on prepared baking sheets, spacing cookies 2 inches apart.
Bake for 12-15 minutes, until the edges are golden brown and the centers still look slightly soft. Do not overbake, cookies will firm up as they cool.
Let cookies rest on the baking sheet for 5 minutes, then transfer to a cooling rack to cool completely.
To make the filling: In a medium bowl, beat the ¾ cup softened butter with an electric mixer until smooth and creamy, about 2 minutes.
Gradually add the 2 ½ cups powdered sugar, about ½ cup at a time, beating on low speed until incorporated, then increase to medium speed.
Add the 1 teaspoon vanilla extract and 1 tablespoon milk, beating on medium-high speed until the filling is light, fluffy, and smooth, about 2-3 minutes.
Once cookies are completely cool, match them into pairs of similar size. Pipe or spread about 1½ tablespoons of cream filling onto the flat (bottom) side of one cookie.
Notes
Don't skip the resting time: Letting cookies rest on the baking sheet for 5 minutes helps them set without becoming too crisp.
Soft centers are key: Cookies should look slightly underdone when you remove them from the oven. They'll continue to bake as they cool, resulting in that perfect soft, chewy texture.
Room temperature butter is essential: For both the cookies and filling, butter should be softened but not melted. This creates the right texture and ensures ingredients combine properly.
Adjust filling sweetness: If you prefer a less sweet filling, reduce powdered sugar to 2 cups.
Make them smaller: Use a small cookie scoop (1 tablespoon) to make 24 mini cream pies, perfect for lunchboxes!
Uniform cookies matter: Try to make all cookies the same size so they're easy to pair up when assembling.
Storage Instructions
Store oatmeal cream pies in an airtight container at room temperature for up to 3 days, or in the refrigerator for up to 5 days. For longer storage, wrap individually in plastic wrap and freeze in a freezer-safe container or zip-top bag for up to 1 month. Thaw at room temperature for 1-2 hours before serving.