Upon leaving the Enolian homeworld, Archer and Trip are mistakenly identified as smugglers and arrested. The two men are placed on a prison transport headed for the penal colony known as Canamar. Among their fellow prisoners are the menacing Kuroda, a hulking Nausicaan and a young, talkative alien named Zoumas.
Back on Enterprise, T'Pol manages to convince an Enolian official that Archer and Trip are innocent and he arranges for their safe return. Just as Archer and Trip are about to be set free, however, Kuroda breaks free and, with the Nausicaan's help, takes down the guard and pilot. With the pilot out of commission, there's no one to fly the ship. Hoping to figure out an escape plan of his own, Archer volunteers to pilot the craft. He also pretends to be a smuggler, hoping that Kuroda will come to trust him. When the vessel comes under attack from Enolian patrol ships, Archer also convinces Kuroda to allow Trip to assist them. Trip manages to create a plasma cloud that, once ignited, fends the patrol ships off, allowing prison transport jumps to warp.
Meanwhile, Archer has also managed to covertly transmit a distress signal from the prison ship, and the Enterprise crew picks up on it. Unfortunately, the Enolian official has bad news — his superiors have issued orders to destroy the prison transport. Although Archer and Trip are still onboard, the Enolians are determined to get rid of the violent Kuroda. If the crew is to save their fellow officers, they have to find the prison transport before the Enolian patrol ships do.
Back on the prison transport, Kuroda is impressed with Archer's ploy to fend off the Enolian ships. In fact, Kuroda has come to respect Archer and asks the captain to join him on his next endeavor. As the two men talk, Kuroda reveals that he was 14 when he first spent time in a penal colony. He was innocent, but he still spent five years in prison, where he picked up many new skills. He started making a living as a criminal after he was released. Kuroda also finally reveals where he's taking the transport: a trading outpost called Tamaal. Once there, they will rendezvous with another ship and Kuroda will set the transport on a decaying orbit. The other prisoners will be incinerated. Naturally, this doesn't sit well with Archer, but when he tries to talk Kuroda out of it, the other man merely dismisses him.
Archer is determined to save the other prisoners and enlists Trip's aid. Trip is freed under the pretense of fixing a docking hatch, but Archer wants him to overpower the Nausicaan so they can take control of the ship. Trip manages to render the hulking alien unconscious, but the commotion draws the attention of Kuroda, who stuns Trip with a weapon and realizes that Archer has been plotting against him all along. The transport docks with another ship at the Tamaal rendezvous point ... but when the doors open, Reed, Mayweather and a Starfleet security guard appear! The crew manages to get all of the prisoners off the transport, which is now in a decaying orbit, but Kuroda refuses to come. He would rather die than return to prison. As the others leave, he remains on the transport and the vessel explodes.
Back on Enterprise, the Enolian official demands a report for his superiors. Archer, however, is in no mood to give one. He tersely informs the official that Kuroda is dead and that he and Trip were falsely arrested. Angrily, Archer wonders how many others are on their way to Canamar that don't belong there.