Maureen is rounded up when the city of Chicago is captured by Gileadean forces. Along with other women declared as Unwomen and bound for the Colonies, she is deported to a warehouse near Boston where they are put in cages.At night, Commander Lawrence shows up in the warehouse with his Handmaid June ("Ofjoseph"). He hands June a binder and tells her she can save five of the captives, who will be made into Marthas. As she will not choose, he tells her she is condemning all of them to death. June says that it is actually him and Gilead who are responsible for their deaths. Lawrence answers that it is a “technical distinction” that won’t matter to the women in question. June returns to the car and cries.
Maureen turns out to be one of the women that June eventually chooses to become Marthas. She is assigned to the brothel Jezebel's.
Maureen enters a suite in Jezebel's and finds High Commander Winslow’s bloodstained body, June sitting next to him. She thanks June for saving her life, revealing herself as one of the five Chicago women that she saved. She tells June to escape through a service elevator. Later the Marthas get to work in High Commander Winslow’s former suite. They clean up the suite leaving no trace of what happened, and stealthily dispose of High Commander Winslow's body in the incinerator.