Linda hides out in her grandmother's garret (attic), a dark, cramped crawl space infested with rats, mice, and "little red insects." Able to see her children through a small opening in the wood but unable to communicate with them, she spends several miserable months suffering a myriad of ills, including fever and frostbite. Meanwhile, Dr. Flint tries to bribe her children into telling him about Linda's whereabouts.
The title of this chapter is "The Loophole of Retreat." A "loophole" provides a means of escape from a seemingly impossible situation. For example, a criminal captured at the scene of a crime may be set free because the evidence used to indict him was obtained without a proper search warrant. Similarly, a shrewd business owner may avoid paying taxes because she understands the intricacies of tax loopholes. However, the meaning of the word "retreat" depends primarily on its context. For example, a writer's retreat may be a refuge or sanctuary where writers overwhelmed by the pressures and demands of everyday life can go to relax and nurture their creativity, whereas a military retreat connotes an image of soldiers fleeing from the battlefield to escape their enemies. Linda's "loophole of retreat" offers both escape and sanctuary. When describing the oppressive darkness of her "loophole," Linda concludes, "It seemed horrible . . . Yet I would have chosen this, rather than my lot as a slave".
Linda's daring escape invites comparison to the story of Henry "Box" Brown, who escaped slavery by having himself packed in a crate and shipped to a Free State. But although Henry spent only hours — or, at most, days — in his box, Linda spends seven years virtually buried alive. She survives her harrowing ordeal by first transforming her mind — continually reminding herself that although confined in a cramped attic, she is free from Dr. Flint — and then transforming her space from a virtual grave to a "retreat."
For enslaved Africans, freedom generally meant crossing the boundaries from Slave States to Free States. After the passage of the Fugitive Slave Act in 1850, it meant crossing the boundaries between the United States and Canada or Mexico. But it also meant crossing mental boundaries and escaping the plantation mentality created and perpetuated by slaveholders who brainwashed blacks to believe that their subservient status was ordained by God. Escape generally involved breaking out of a confined, limited space. But Linda's escape entails movement from a larger, limited space to a confined space where, although physically imprisoned, she feels psychologically free.
Linda's seclusion in her "small, dark enclosure" symbolizes the narrow role — restricted because of both race and gender — prescribed for black women by white America.
Linda's ordeal also addresses the themes of madness and confinement prevalent in women's literature, such as Charlotte Perkins Gilman's short story, "The Yellow Wallpaper," in which a woman goes mad as a result of being isolated from society by her controlling and overbearing husband. But unlike Gilman's protagonist, Linda staves off madness by sewing for her children and writing letters to Dr. Flint, which she has postmarked from New York, to confuse him as to her whereabouts. Her ability to write not only helps her maintain her sanity, but it enables her to transform and transcend her reality.