Jacobs uses the motif of chains and confinement throughout the book to describe the experience of enslavement and her long attempt to break out of it. For instance, in Chapter 14, she describes how her father's former enslaver gifts Linda's new baby a gold chain:

When we left the church, my father’s old mistress invited me to go home with her. She clasped a gold chain round my baby’s neck. I thanked her for this kindness; but I did not like the emblem. I wanted no chain to be fastened on my daughter, not even if its links were of gold. How earnestly I prayed that she might never feel the weight of slavery’s chain, whose iron entereth into the soul!

The chain seems to be a genuine offer of "kindness," but Linda sees it also as a symbol of the new baby's confinement, both in the institution of slavery and in the ever-more-complicated family tree that her family and their enslavers are all a part of. The gold chain recalls the French philosopher Jean-Jacques Rousseau's famous statement that "Man is born free but everywhere is in chains." Rousseau was writing about the theory of the social contract, or the idea that humans in society are bound by obligations to one another. Linda sees her daughter as a person who is free because she does not yet know what it means to be enslaved. The gold chain is not meant to literally confine the child, but to Linda it represents the social contract of the pre-Civil War South: white enslavers control all the wealth, and they use it to bind Black people to them from birth. If this white woman's kindness turned against Ellen, she could just as easily use the chain to strangle the child.

To Linda, her children themselves confine her to the treacherous social world she inhabits. The chapters in which she describes her children's births are entitled "A Link to Life" and "Another Link to Life." This language, like Rousseau's language, has two edges. Benny and Ellen give Linda something to live for, but they are also more links in the chain that wraps around her and keeps her on the plantation. Without them, she might find it easier to leave. It is ambiguous whether "leaving" for her would entail running away or dying, but dying no longer feels like an option to her once the children are born. A woman in metaphorical chains, she is obligated to live for them.

One of the most salient examples of confinement is Linda's seven-year stay in Grandmother's garret before she can run away from Dr. Flint in earnest. In Chapter 18,  before Grandmother's space is ready for her, she hides under a neighbor's floorboards to avoid being detected by Dr. Flint:

In my shallow bed I had but just room enough to bring my hands to my face to keep the dust out of my eyes; for Betty walked over me twenty times in an hour, passing from the dresser to the fireplace.

Jacobs's memoir is important in part because it disabuses Northerners of the idea that there is a binary between enslavement and freedom. Confinement is an integral and horrifying part of Linda's journey to freedom. Her description of the claustrophobic atmosphere under the floorboards is literal, but it is also representative of just how completely trapped Linda is by her circumstances. To be enslaved, the memoir argues, is to be confined.