True leadership requires balancing absolute faith in divine promises with a genuine commitment to diplomacy. Before engaging in battle with Sihon, a sincere attempt at peace is initiated through diplomatic messengers [ביאור שטיינזלץ]. Although earlier accounts mention that the entire nation of Israel sent these envoys, Moses is also presented as the one directing the effort. Commentators offer several ways to understand this shift in the narrative. Some suggest there were actually two separate delegations dispatched at different stages of the journey [מלבי״ם]. Others propose a division of labor: Moses sent a letter of peace, while the people prepared for conflict and sent a message of war [רא״ש, דעת זקנים]. Alternatively, Moses simply acted as the nation's representative, exercising political wisdom on their behalf [שפתי כהן].
The messengers were dispatched from an area known as the wilderness of Kedemoth, a detail that sparks three distinct interpretations. The geographic approach views this as a specific physical place [אבן עזרא, נתינה לגר] situated in the east, as its name implies an eastern direction [חזקוני, ביאור שטיינזלץ]. A historical perspective suggests the name describes the area's physical transformation. It conveys the idea of "before," indicating that it was previously a barren desert until God brought forth water from a rock, turning it into a well-watered region [רא״ש, פענח רזא, הדר זקנים, דעת זקנים, בכור שור].
The conceptual approach, however, argues that since no known geographic location bears this exact name, the term hints at the concept of precedence. Moses learned from the ways of God and from the Torah, which preceded the creation of the world. Just as God offered the Torah to the nations of the world knowing they would refuse it, and just as He sent Moses to warn Pharaoh gently before bringing plagues upon Egypt, Moses understood that he must precede any military action with a call for peace. He took this diplomatic step on his own initiative, even without an explicit divine command [רש״י, מזרחי, תורה תמימה, שפתי חכמים, גור אריה, משכיל לדוד, ברכת אשר, ברטנורא].
The delegation approached Sihon with terms of peace, raising a question as to why he received this diplomatic courtesy while Og, the king of Bashan, faced immediate war. The primary distinction lies in the historical ownership of the territories. Most of Sihon's land originally belonged to the nations of Ammon and Moab, making a peace offering both permissible and appropriate. In contrast, Og ruled over territory belonging to the Canaanite nations, with whom offering peace was strictly forbidden [רא״ש, הדר זקנים, דעת זקנים, חזקוני].
Beyond these legal boundaries, the peace offering served strategic and educational purposes. Moses presented fair terms for safe passage and the purchase of food, fully aware that Sihon would reject them. This anticipated refusal was designed to show the Israelites that God was hardening the king's heart, thereby amplifying the magnitude of the miraculous victory they were about to achieve against such a formidable opponent [אברבנאל, ביאור יש״ר]. Furthermore, extending a hand in peace prevented panic and mass flight among the remaining Canaanite kings. Most importantly, it established a lasting moral precedent: even when war is an absolute obligation, it must only commence after providing a genuine opportunity for negotiation [שפתי כהן, ביאור שטיינזלץ].