"Catching Out" is slang for riding a freight train. In three interwoven stories, this doc follows three contemporary hobos—a seasoned eco-activist named Lee (There's Something About a Train zine), a young nomad named Jessica (Transient Ways), and a tramp couple known as Switch and Baby Girl—as they navigate between the constraints of society and the freedom of the rails. The film explores Lee's intimate connection with nature and Jessica's bohemian upbringing. Meanwhile, Switch and Baby Girl confront society as they retire from the rails to raise their son Isaiah.