New Characters
No. 406 (also known as "Rip van Winkle"): a Party follower who was held in prison for twenty years before coming to Rubashov's prison

No. 380 or Bogrov: Rubashov's old close friend and a distinguished Party official

Summary
On the morning of the tenth day after Rubashov's arrest, the inmate of cell No. 406 began regularly tapping out the message, "ARIE, YE WRETCHED OF THE EARTH." Meanwhile, Rubashov and No. 402 have developed a small friendship, with No. 402 telling tales from his officer days. No. 402 responds to Rubashov's query by saying that No. 406 is "RIP VAN WINKLE." He explains that Rip van Winkle was arrested in a foreign country for helping lead its revolution, and served twenty years of a lifetime sentence there, mostly in solitary confinement. Upon going to the Party homeland after his release, he was promptly arrested.

Rubashov is taken to the prison barber to be shaved on the afternoon after Rip van Winkle's arrival. The barber calls him "Citizen Rubashov" before furtively giving him a slip of paper that reads "'Die in silence.'" This message from outside the prison gives Rubashov cause to wonder about its meaning, and he begins to consider accepting Ivanov's offer. He considers how he wants to die.

On the morning of the eleventh day after Rubashov's arrest, he goes out to the prison yard for the first time. He is joined by Rip van Winkle, who is a small, elderly man with eyes that have a simple friendliness. As they walk in the yard, Rubashov looks up at No. 402's cell, then hears Rip van Winkle "humming the tune of 'Arise, ye wretched of the earth.'" Rubashov struggles to decipher the contents of Rip van Winkle's mind. The following two days, the pair again go out in the yard after breakfast. On their third walk, Rubashov brings his pencil and note-book. Rip van Winkle draws a map of the Party homeland three times on the note-book paper and tells Rubashov he can do this from memory because he has practiced it for twenty years. Rubashov and Rip van Winkle tell each other that their imprisonment was accidental, and Rip van Winkle, saying that we will all get to the homeland, maintains, "'One must not give up hope.'"

On the evening of the day before Ivanov's 14 days expire, Rubashov senses a strange feeling in the prison air. When he talks to No. 402, he learns that "POLITICAL DIFFERENCES ARE BEING SETTLED." No. 402 adds that Hare-lip has told him of the night's executions of political criminals. Rubashov sits and thinks about these executions, remembering Arlova's scent and sensing the deep silence, before learning that No. 380 is about to be shot. No. 402 says that No. 380 is Bogrov, the former Commander of the Eastern Fleet. Bogrov is an old comrade of Rubashov's; they shared their post-1905 exile and became very close friends. The prisoners begin to drum as Bogrov and his guards come up the corridor. Rubashov sees Bogrov being dragged by his cell and hears Bogrov yell for Rubashov as he reaches the end of the corridor. Rubashov lies back down, thinks of Arlova's execution, and falls to sleep with exhaustion.

Analysis
The question of how Rubashov should die illustrates his relationship with the Party he helped build. He wonders if it is better to die silently in one last service to the Party or to serve his own aims instead. Rip van Winkle spent twenty years of his life silently serving the Party and was rewarded by being sent to prison two weeks...