Homemade Oreo cookies are just like the iconic cookie, only bigger and better! They are perfect for dunking and you can let your imagination go wild with filling flavors... or put as much filling as you want.
In mixer bowl, beat softened butter until smooth and creamy. Add powdered sugar and mix until combined.
Add cocoa powder, salt, vanilla and coffee extract. Mix until incorporated.
Stir in flour until a thick dough forms, it will be on the dry side but should come together. Form dough into a disk and wrap in plastic wrap. Chill for 15-30 minutes.
Preheat oven to 350°F.
Roll chilled dough out on a surface dusted with cocoa powder or a mixture of cocoa powder and flour. When the dough is 1/8-thick cut into 3 inch circles.
Place circles at least 1 inch apart on a nonstick or parchment lined cookie sheet and bake for 8 minutes.
Cool for 5 minutes on the cookie tray before removing to a wire rack to cool completely.
Once cookies are fully cooled, make the filling.
Filling
Cream together the butter and shortening until smooth and creamy.
Add powdered sugar and vanilla, mix on low speed until combined and then on medium for at least 2 minutes.
This frosting should be thick so it doesn't squish out when you bite the cookie. However, if it needs a little bit more moisture add a teaspoon or two of water or milk and mix again until combined.
Pipe or spread over half the cookies and top with the other half of the cookies.
Allow to sit out in a cool place for the filling to set up.
These cookies are best enjoyed in the few days after being assembled as the cookies will soften with time. However, they can be stored at room temperature for up to a week.
Notes
You can omit the coffee extract if you would like, but it gives the chocolate flavor a boost.For longer storage, freeze the cookies and the filling separately for up to three months. Defrost and assemble when you are ready to enjoy them. Feel free to make more filling if you like overstuffed Oreos. Or try using different flavorings and extracts to create your own Oreo flavors!