Special Guest Stars Jim Beaver as Apocalypse World Bobby Singer Guest Stars Samantha Smith as Mary Winchester Ruth Connell as Rowena MacLeod David Haydn-Jones as Arthur Ketch Richard Speight, Jr. as Trickster / Gabriel Katherine Evans as Maggie Christian Keyes as Apocalypse World Michael Felicia Day as Apocalypse World Charlie Bradbury Alexander Cendese as Angel Commander Co Starring Dagan Nish as TBD James Lafazanos as Resistance Traitor Jeffrey Joseph as Andy Patrick Carlos as Fake Prisoner Uncredited Misha Collins as Apolcaypse World Castiel