When a father sells his daughter as a Hebrew maidservant, the fundamental expectation is that the purchasing master will eventually take her as a wife. However, a situation may arise where the young woman does not find favor in the master's eyes, and he no longer wishes to marry her [רש״י, רשב״ם, ספורנו, חזקוני]. Her lack of favor does not imply any flaw in her character or actions, but simply an absence of grace and affection from the master [גור אריה, תורה תמימה]. In such a case, even if her original purchase was intended for marriage, the master should not marry her if he harbors feelings of resentment toward her [ספורנו].
The primary approach among commentators is that the initial money used to purchase the maidservant effectively serves as her betrothal money, requiring no further act of betrothal [רש״י, מזרחי]. The concept of designation implies a profound connection, drawing them together to become one flesh [כתב והקבלה, חזקוני]. A duality in the traditional reading of the text reveals the underlying tragedy: the master originally bought her with the express purpose of designating her as a wife for himself, yet ultimately refrained from fulfilling that purpose [אבן עזרא, שד״ל, כתב והקבלה].
Because the anticipated marriage never materialized, she must be redeemed. This obligation of redemption falls heavily upon both the father and the master. Once it becomes clear that the master will not marry her, the father is strictly forbidden from leaving his daughter in that household and must make every effort to redeem her [רמב״ן, ספורנו, שד״ל]. Simultaneously, an active duty is imposed upon the master to facilitate her freedom. He must assist in her redemption by deducting the value of the years she has already worked from her redemption price, allowing her to go free in exchange for the remaining relative balance [רש״י, רשב״ם, רא״ש, חזקוני].
Furthermore, she is protected by a strict prohibition against being sold to a foreign people. Commentators offer two primary perspectives on the nature of this restriction. One approach understands this literally, warning the father and the court never to sell the young woman to a Gentile. Although a Hebrew slave may be sold to a non-Jew, this is explicitly forbidden regarding a maidservant in order to protect her dignity and prevent the degradation of Israelite women [רמב״ן, רבנו בחיי, טור]. A second perspective interprets the foreign people as any Israelite stranger outside of her immediate family. According to this view, the father cannot sell his daughter into servitude a second time to another man, nor can the master sell her onward [רש״י, אבן עזרא, שד״ל, חזקוני]. Selling her to an unfamiliar family is equated to selling her to a foreign nation, as she would become subjugated to an alien household without the hope of being redeemed by her own relatives [שד״ל, כתב והקבלה].
The underlying reason for this strict prohibition is rooted in the concept of betrayal. Commentators identify two complementary meanings within this betrayal. First, it represents a profound breach of trust. The master betrays the young woman by failing to fulfill his promise of marriage, and the father betrays her if he attempts to sell her to someone incapable of marrying her [רשב״ם, רמב״ן, ספורנו, בכור שור]. Second, the concept of betrayal shares a linguistic root with the word for a garment. Because the master had already symbolically spread his cloak over her by designating her for marriage, he loses any right to sell her to another [קיצור בעל הטורים, רבינו בחיי, כתב והקבלה]. Drawing these ideas together, the betrayal of trust is likened to an empty garment. The master or the father provided the young woman with the outward appearance and protective shell of a commitment, but ultimately emptied it of its proper human and moral substance [רש״ר הירש].