A remarkable social and psychological scenario unfolds when a servant reaches the legal moment of his freedom but freely chooses to surrender his liberty and remain in his master's house. This choice highlights the unique working conditions mandated by the Torah and the complex relationships between people, as well as between humanity and God.
The physical procedure of piercing the servant's ear is detailed elsewhere, making its appearance here a way to complete the previous instruction about giving a generous severance gift. Supplying the servant with abundant property upon his departure guarantees that a decision to stay stems from genuine affection, rather than a fear of starving if he leaves empty-handed [אלשיך]. Because of this connection, the subsequent instruction to treat a maidservant similarly refers strictly to providing her with a severance gift, as a female servant does not undergo the ear piercing procedure [רש״ר הירש, ברכת אשר על התורה].
If the servant decides to stay, he must state his intention twice: once while still officially bound, and again at the exact moment of his scheduled release [מלבי״ם]. His motivation might be a deep-seated anxiety about assuming the heavy responsibilities that come with being a free individual [ביאור שטיינזלץ]. He justifies his choice by expressing love for his master and his master's household, which specifically means the master's wife and children [תורה תמימה, נתינה לגר]. Consequently, the ear piercing procedure depends on strict conditions of family completeness and mutual affection. The master must have a family, and the love must be fully reciprocated; the master is required to love the servant just as the servant loves him [תורה תמימה, מלבי״ם].
The ideal working conditions are defined by absolute equality between the master and the servant. The master must match his own living standards with those of his worker in food, drink, and lodging. If the master eats fine bread and sleeps on a soft bed, he is forbidden from giving his servant basic bread or making him sleep on straw. Furthermore, the master cannot demand labor without first providing the servant's meals. These rigorous demands led to the famous saying that anyone who buys a Hebrew servant essentially buys a master for himself. Additionally, this arrangement requires both parties to be in perfect health; if either the master or the servant is ill, the ear piercing procedure is canceled [תורה תמימה, מלבי״ם].
Despite these comfortable conditions, the servant's choice to remain is ultimately viewed as a spiritual failure. It is only at this moment of willingly surrendering his freedom that he is truly branded with the title of a slave. By making this choice, he abandons his trust in God, choosing instead to place his security in a human being [שפתי כהן]. The pierced ear serves as a badge of shame for someone who heard the divine declaration at Mount Sinai that the Israelites are servants to God alone. By choosing to subjugate himself to another person, he effectively regresses to the disgrace of slavery in Egypt [אלשיך].