As the Israelites approach the Transjordan, they stand on the edge of Amorite territory. Before drawing their swords, they initiate a diplomatic effort with Sihon, the powerful king who rules the region, by sending messengers to his court [ביאור שטיינזלץ]. Even though God had already instructed them to fight Sihon, the decision to first offer peace was an independent choice. This initiative was rooted primarily in the deep moral obligation to actively pursue peace before resorting to violence [צאינה וראינה].
Beyond this moral duty, there were highly practical reasons for the approach. Moses understood that the Israelites would not immediately conquer all the nations of Canaan, and he envisioned the Transjordan as a continuous, fertile region for the tribes to settle. If Sihon accepted the peace offer, the land would remain whole, and its inhabitants would simply pay taxes without their cities being destroyed [רמב״ן, ביאור ישר, אברבנאל]. Furthermore, Sihon was widely regarded as the strongest king in the region, serving as a protector for the other Canaanite rulers. If he surrendered peacefully, the resulting fear would likely cause the surrounding nations to submit as well [אברבנאל].
A question arises regarding who actually dispatched these messengers, as different historical accounts attribute the action either to the Israelites or to Moses. The primary approach among commentators is that there is no contradiction, as Moses and the Israelites are viewed as a single entity. The leader of the generation is considered equal to the entire generation, reflecting a profound unity and devotion between the shepherd and his people [רש״י, העמק דבר, חומש קה״ת, משכיל לדוד].
Other perspectives suggest a more practical division between Moses and the nation. One view proposes that two distinct letters were sent simultaneously: Moses sent a message of peace, while the Israelites sent a declaration of war [חזקוני]. Another explanation points to two separate diplomatic missions occurring at different times. Moses sent an initial peace offering while the nation was still far from the border, and the Israelites sent a follow-up message once they arrived at the boundary [מלבי״ם].
Finally, some suggest that highlighting the Israelites as the senders points to a calculated military strategy by the people. Sihon’s cities were heavily fortified and difficult to breach. The arrival of the messengers was intentionally designed to draw Sihon out, prompting him to gather his army and leave his protected strongholds for the open battlefield. This clever maneuver allowed the Israelites to defeat his entire military force in a single confrontation, capturing the cities completely intact and ready for immediate habitation [שפתי כהן, מלבי״ם, צאינה וראינה].