Preheat the oven to 375 F/190 C and line two baking sheets with parchment paper.
In a large bowl, whisk together the brown sugar, egg, egg yolk, oil, sour cream, espresso, and vanilla until well combined.
Fold in the flour, cocoa powder, salt, baking soda, and baking powder until just combined.
Scoop the dough with a standard (two tablespoon) cookie scoop onto the prepared baking sheets spaced at least two inches apart. Sprinkle with some of the oreo crumbs.
Bake for 7-8 minutes. (for my oven, 7 minutes is perfect!)
Allow them to cool completely on the tray while you make the filling.
To make the buttercream, mix the butter in a mixing bowl until smooth and lump-free.
Add in the powdered sugar and mix on low until combined, then mix on medium-high speed until it looks white and fluffy.
Mix in the espresso on low until combined, then mix in the Oreo crumbs.
To assemble, pipe a dollop of the buttercream onto the bottom of one cookie and sandwich it with the other. Enjoy!