Filled Devil Dogs

A homemade copycat of the Drake’s classic, filled devil dogs are pillowy chocolate sandwich cookies with a fluffy white cream filling between them. The cookies bake up at high heat for just five minutes, which keeps them soft and cake-like rather than crisp. The filling is the throwback move: a flour-and-milk paste cooked into a thickened slurry, then beaten into creamed butter, shortening, and sugar for a smooth, marshmallow-meets-buttercream texture (sometimes called Ermine or boiled-milk frosting).

Both halves matter equally. The hot oven gives the cookies their puffy, oblong silhouette, while the cooked-flour filling stays stable at room temperature without weeping or cracking like a typical buttercream would. Spread, sandwich, eat. Eighteen sandwiches that taste better than the cellophane-wrapped originals from the gas station.

Pro Tips

• Bake at the full 425°F (220°C); lower temperatures cause spreading instead of puffing
• Pull cookies at 5 minutes even if they look slightly soft; they firm up on the pan during a 1-minute rest
• Cook the milk-flour mixture for the filling until very thick (pudding consistency); thin slurry leaves a runny filling
• Beat the cooked paste into the creamed fats while it is just warm, not hot; hot paste melts the fats
• Beat the filling for a full 4 minutes to incorporate air and lighten the texture

Variations

• Add a tablespoon of cocoa to the filling for chocolate-on-chocolate
• Use peppermint extract in place of vanilla in the filling for chocolate-mint sandwiches
• Substitute butter for the shortening in the filling for richer flavor (less stable for transport, more delicious)