Preheat your oven to 350 degrees/F and prepare 3 8-inch cake pans by rubbing generously with vegetable shortening and dust with unsweetened cocoa powder.
In the bowl of a stand mixer equipped with a whisk attachment, add the flour, sugar, cocoa powder, baking powder, baking soda, salt, and espresso powder and whisk until well combined.
Add in the vanilla, eggs, milk, and vegetable oil and mix until there are no dry spots remaining.
Add in the boiling water last and mix on low speed. Slowly increase to high for 1-2 minutes.
Divide the batter evenly between the three cake tins and bake for 25-30 minutes or until a toothpick inserted in the center of each cake comes out clean.
Remove from the oven and allow the cakes to cool completely on a wire rack.