Whisk together the flour, cocoa, baking soda, salt and espresso powder. Set aside.
1 cup flour, 3/4 cup cocoa, 1 teaspoon baking soda, 1/4 teaspoon salt, 1 1/2 teaspoon instant espresso powder
In the bowl of a stand mixer cream together the butter and both sugars until light and fluffy.
8 tablespoon unsalted butter, 2/3 cup brown sugar, 1/4 cup sugar
Beat in the egg and vanilla extract until fully incorporated.
1 egg, 1/2 teaspoon vanilla extract
With the mixer on low, gradually add the dry ingredients mixing only until just incorporated; avoid over mixing. Stir in the chocolate chips.
1 cup chocolate chips
Separate the dough into 2 equal portions. Roll each portion into a log about 12 inches long. Wrap tightly and refrigerate the dough until firm enough to slice.
Preheat the oven to 350°F and line two baking sheets with parchment paper or silicone mats.
Cut the logs into 1/4" slices. Place the slices about 1 1/2 inches apart on the prepared sheets. Bake for about 10 minutes or until the cookies look just barely set. allow to cool on the pan for a couple of minutes before transferring to a wire rack to cool completely
To make the filling:
In a medium mixing bowl, beat the butter, cream and vanilla extract together until smooth and creamy.
Gradually beat in the powdered sugar. The mixture should be creamy but stiff enough to hold peaks.
2 cup powdered sugar
To assemble the sandwich cookies:
Pipe a small amount of the filling on the backs of half the cookies.
Place a second cookie on top of the filling and press gently until the filling almost reaches the edges of the cookies.
Store the cookies in an air tight container
Notes
If you prefer you can substitute the vanilla extract in both the cookies and the filling for a different flavor extract or emulsion such as almond extract or princess emulsion. Be aware that if you choose a real nut extract rather than an artificial one, this recipe will no longer be nut free.