Parting with a loyal servant after years of dedicated service, coupled with the obligation to provide a generous severance gift, can easily evoke feelings of reluctance and financial strain within an employer. To uproot this reluctance, an appeal is made directly to the master's conscience, offering economic, moral, and spiritual perspectives. The primary approach among commentators is that the employer's hardship does not stem from the actual release of the servant, as it was known from the start that the term of service was limited to six years. Rather, the struggle lies in the financial burden of the severance gift, which requires parting with abundant resources from the flock, the threshing floor, and the winepress [רשב״ם, ספורנו, העמק דבר, רש״ר הירש, ביאור יש״ר, שפתי כהן, חזקוני]. Conversely, others suggest that the difficulty is indeed the separation itself. Unlike a permanent servant, the master is forced to surrender highly capable workers who were completely under his authority, and he must now actively assist the departing individual in starting a new chapter [שד״ל, ביאור שטיינזלץ].
To soften this reluctance, the master is reminded that the servant provided double the value of a standard hired laborer. Commentators explore the exact nature of this double output, with one perspective focusing on the length of employment. In antiquity, the standard contract for a hired worker was often three years; thus, a six-year term yielded exactly twice the labor [אבן עזרא, רשב״ם, רבנו בחיי, רא״ש, תולדות יצחק, הדר זקנים, חזקוני, בכור שור, ביאור שטיינזלץ]. This three-year cycle was specifically designed to account for leap years, ensuring neither employer nor employee lost work hours to the fluctuating calendar [הדר זקנים, בכור שור, דעת זקנים]. However, some reject this calculation, arguing that hired laborers did not have a fixed three-year term, and the comparison merely emphasizes that the servant worked for an exact, measured period [רשב״ם, שד״ל].
Another perspective shifts the focus from the duration of employment to the demanding nature of the work itself. While a standard hired laborer is contracted for specific tasks and works only during the day, a servant is completely bound to the master's needs, available for any required chore [שד״ל, אם למקרא]. Furthermore, the servant's long-term presence builds a level of trust and continuity that allows him to handle significant responsibilities, unlike a temporary day laborer who might unexpectedly leave [העמק דבר]. The Sages highlight the extremity of this dedication by noting that the servant essentially works day and night. This refers to the master's right to pair the servant with a Canaanite maidservant to produce children who remain the master's property, an arrangement that can be enforced even against the servant's will [רש״י, אור החיים, מזרחי, רבנו בחיי, תורה תמימה, ריב״א, שפתי חכמים, רלב״ג, מלבי״ם, גור אריה, משכיל לדוד, דברי דוד]. Nevertheless, commentators clarify that enduring such conditions is not a strict prerequisite for receiving the severance gift, as unmarried servants and maidservants are equally entitled to it. Ultimately, the reminder of the servant's immense contribution is designed to inspire a generous spirit, encouraging the master to recognize the profound benefit he received and to send the worker away with a whole heart [תורה תמימה, ברכת אשר, אלשיך].
These moral and economic appeals are accompanied by a divine promise of blessing in all of the master's endeavors. A foundational principle is that whenever financial sacrifice is required to fulfill a Commandment, God guarantees that the individual will suffer no true loss, as divine blessing will compensate them and enrich their yield [ספורנו, חזקוני, בכור שור, שפתי כהן]. Yet, this spiritual assurance does not exempt the master from personal effort. The promise specifies that the blessing will rest upon all that the person does, emphasizing the necessity of working through natural means to create a vessel for success. One cannot sit idle and rely on miracles; rather, human effort is required, and God will complete the task by infusing it with His blessing [תורה תמימה, רלב״ג, חומש קה״ת, שפתי כהן].