Heat oven to 350°F. Line baking sheets with parchment paper.
For the cookies:
In a large mixing bowl, cream together butter and sugars until light and fluffy. Add vanilla and eggs, one at a time, beating to incorporate after each addition.
1 cup unsalted butter, 1 cup sugar, ¾ cup brown sugar, 1 tsp vanilla, 2 eggs
In a separate bowl, whisk together flour, cocoa, , baking powder, baking soda and salt; gradually add the dry ingredients into the creamed mixture, beating just to combine, do not over mix.
1 ¾ cup flour, 1 ¼ cup cocoa, 1 tsp baking powder, 1 tsp baking soda, ½ tsp salt
Scoop the dough into about 1” balls and place about 2” apart on the prepared baking sheets. Using the bottom of a glass, slightly flatten each ball.
Bake 8-10 minutes until puffy and just set. Cool on pans for 5 minutes before moving to racks.
For the filling:
In a large mixing bowl, cream butter, brown sugar and powdered sugar. Add flour, vanilla and salt; mix until well incorporated and the mixture is a smooth, spreadable consistency.
16 tbsp unsalted butter, 1 cup brown sugar, 1/2 cup powdered sugar, 1 cups flour, 1 tsp salt, 1 tsp vanilla
Fold in the mini chocolate chips and crushed Oreos just until evenly distributed. Spread, scoop or pipe the filling onto the flat bottoms of cooled cookies and top each with another cooled cookie, pressing down gently to form a sandwich.
2/3 cup mini chocolate chips, ½ cup crushed Oreos
Notes
When I'm making these for my holiday trays, I make them about half size, maybe slightly smaller. If you are concerned about raw flour, you can heat treat the flour for the cookie dough filling by spreading it in a thin layer on a baking sheet and heating it in your oven at 300°F for about 10 minutes. If you take this step, make sure to completely cool the flour before adding it to the filling or you will melt your butter. Be aware that this may change the texture and flavor of the filling.