These are real deal, authentic whoopie pies (also known as gobs). Cakey chocolate cookies with an old-fashioned, flour-based (NO marshmallow!) filling --a classic! Recipe includes a how-to video!
Combine milk and flour in saucepan and whisk until combined. Set over medium-low heat and whisk constantly until mixture is thickened to a near paste-like consistency that wants to cling together.
1 cup whole milk, ⅓ cup all-purpose flour
Remove from heat and allow to cool completely, stirring occasionally to prevent a skin from forming. Set aside while you prepare your cookies.
For the cookie shells:
Preheat your oven to 450F (235C) and line several baking sheets with parchment paper. Set aside.
In a large mixing bowl, combine sugar and butter and use an electric mixer to beat until well-combined.
1 cup granulated sugar, ⅓ cup unsalted butter
Add egg and vanilla extract and beat again until pale yellow and well-combined.
1 large egg, 1 teaspoon vanilla extract
With mixer on low-speed, gradually stir in buttermilk. Set aside.
½ cup buttermilk
In a separate, medium-sized bowl whisk together the flour, cocoa powder, baking soda, baking powder, and salt.
2 cups all-purpose flour, ½ cup natural cocoa powder, 1 teaspoon baking soda, ¼ teaspoon baking powder, ½ teaspoon table salt
Gradually add the dry ingredients to the batter until completely combined.
Add very hot water (carefully) and stir until batter is well-combined and smooth. It will be thin like a cake batter. Use a spatula to scrape the sides and bottom of the bowl to ensure ingredients are well-combined.
½ cup steaming hot or boiling water
Drop cookie batter by a heaping Tablespoon onto prepared baking sheets, spacing cookies at least 2” (5cm) apart.
Bake for 5-6 minutes in center rack of 450F (235C) preheated oven, then remove from oven and allow to cool completely before removing from baking sheet. As the cookies cool, prepare your filling.
For the filling
Important note: The roux must be completely cooled before proceeding.
Place butter in a large mixing bowl (or the bowl of a stand mixer) and use an electric mixer to beat until smooth, light, and creamy.
1 cup unsalted butter
While mixing on medium/low speed, add the flour mixture, a Tablespoon at a time, waiting until each spoonful is incorporated before adding the next.
Roux
Scrape sides and bottom of bowl and stir in salt and vanilla extract.
Gradually stir in powdered sugar until completely combined.
1 cup powdered sugar
Pipe or spoon filling onto the bottom of one chocolate cookie and sandwich with another (about 1 ½ Tablespoon of filling per cookie). Enjoy!
Video
Notes
FillingThis filling is prone to breaking/splitting if the butter or roux are too warm when combined. If you notice it separating, refrigerate for 10 minutes then stir very well with an electric mixer on high speed until no longer split.StoringStore refrigerated in an airtight container for up to 5 days.Original recipe notesWhen I first shared this recipe (in the version from my grandmother), shortening was used instead of/in addition to the butter.The cookies originally used ¼ cup of shortening (Crisco) instead of the ⅓ cup of butter, and the filling used ¾ cup of butter + 2 Tablespoons of shortening.