Prep oven and pans. Preheat the oven to 350°F (180°C). Line two large baking sheets with parchment paper (or silicone baking mats). Set aside.
Combine dry ingredients. In a large mixing bowl, sift together the flour and cocoa powder. Whisk in the baking soda, salt, and espresso powder. Set aside. 2 cups (250 g) all-purpose flour ½ cup (45 g) natural unsweetened cocoa powder 1 teaspoon baking soda 1 teaspoons instant espresso powder ½ teaspoon salt
Cream butter and brown sugar. In a large bowl with an electric mixer (hand mixer or stand mixer with paddle attachment), cream together the butter and brown sugar together for 1 to 2 minutes, or until combined. ½ cup (1 stick, 113 g) unsalted butter 1 cup (200 g) packed light brown sugar
Add egg and vanilla. Mix in the egg and vanilla until fully combined. Scrape down the bowl as needed. 1 large egg 2 teaspoons vanilla extract
Alternate dry ingredients and buttermilk. Starting and ending with the dry ingredients, alternate the flour mixture in 3 additions, with the buttermilk in 2 additions. Mix in until just combined with each addition. Be careful to not overmix at this point. 1 cup (240 ml) buttermilk
Scoop the cookies. Using a 1 ½-tablespoon cooking scoop, scoop the whoopie pie batter onto the prepared baking sheets, leaving about 2 inches between each one. Use the back of a spoon to smooth out the batter for each whoopie pie before placing them in the oven.
Bake. Bake for 11 to 13 minutes, or until the tops of the cookies spring back to the touch. Remove from the oven and cool on the baking sheets for 10 minutes, then transfer the chocolate cookies to a wire rack to cool completely.