In a stand mixer with a cookie paddle attached, cream the butter and sugar together on medium speed, until the mixture is light and fluffy, about 2 minutes.
Add the cocoa powder, salt, and vanilla, and mix until incorporated. Add half of the flour and mix.
Add the remaining flour, 1/4 cup at a time, until you get a pretty dry dough. You don’t want the dough to be sticky at all, and it might even crumble just a little. Don’t be worried about a dry dough; we want a crispy cookie that doesn’t spread when baked.
Divide the dough into 3 balls, and pat them together to form a disk. Cover the disks in plastic wrap, and refrigerate for about 15 minutes.
Now, if your world is crazy like mine, and 3 hours, instead of 15 minutes, pass before you get back to baking, let the dough rest at room temperature for 15 minutes. The butter makes the dough super stiff if it’s too cold.
Preheat oven to 350 degrees. Remove plastic from one disk, and roll your dough out between 2 pieces of parchment paper or on a lightly floured surface. Roll the dough thin! We are talking 1/4-inch to an 1/8-inch thick.
Use a 2-inch circle cutter to cut out the cookies.
Place on a cookie sheet and bake for 8 to 9 minutes. It’s super hard to tell when a near-black cookie is done. I baked mine for 10 minutes the first round, and they tasted burnt on the bottom, so you’ll need to adjust as you go.
Repeat with the rest of the dough. Place the cookies on a wire rack to cool.
While the dough is chilling, mix up the cream filling. Using a stand mixer with a cookie paddle attachment, mix the powdered sugar, melted butter, vanilla extract, mint extract, and 1 to 2 drops green food coloring together. Add 1 teaspoon of water at a time, if needed, until the mixture resembles a thick dough that is about the consistency of play dough. Adjust the food coloring to meet your needs.
Divide the filling in half, and roll it into a log that is about 2 inches thick. Roll the log in plastic wrap, and let it chill in the fridge while the cookies are baking.
After the cookies are cool, it’s time to assemble! Remove the filling from the plastic wrap. Using a sharp knife, slice off a piece that is between 1/4- to 1/2-inch thick.
This is the fun part of making your own Oreos. You can have traditional cream thickness, double stuffed, or even triple stuffed.
Stack a cookie, cream, and then another cookie. Press lightly together. Repeat, repeat, repeat.
Store in an airtight container for up to a week.
Notes
A true dark chocolate cocoa powder will give you that almost-black, dark-brown cookie. A Dutch-process cocoa powder will give you what you see in my photos. A traditional cocoa powder will give you a light brown, with a hint of red, cookie. I like the dark or Dutch-process cocoa best for these cookies and highly recommend finding some.
While these cookies can be made ahead, I have found they taste fresher when the cookies and filling are stored separately and put together when they will be eaten within a day.
You can skip the food coloring if you don't want to use it! It's for green coloring purposes only.
My favorite way to serve these cookies is crumbled into a homemade milkshake, but they're delicious with a glass of milk, too.