Devarim 

דברים

When the Israelites approached the territory of Sihon the Emorite, king of Heshbon, God promised Moses this land would be conquered easily, and He urged him to go out and wage war with him. Nevertheless, Moses dispatched emissaries in order to attempt to peacefully traverse Sihon’s territory. It was only after Sihon’s refusal that Moses initiated the war. The Sages learn from here the virtue of peace and the importance of initiating an interaction with words of peace and ways of pleasantness. 

The Holy One, blessed be He, said: I said: “Provoke war with him” (Deuteronomy 2:24), and you send words of peace? “There is no peace, said the Lord, for the wicked” (Isaiah 48:22). See that matters of peace are great, as Israel violated what God said to them: “Provoke war with him,” and He was not angry with them. 

Moses said that he sent messengers to offer them peace “from the wilderness of Kedemot” (Deuteronomy 2:26). What is the meaning of “from the wilderness of Kedemot”? Moses said to God: I learned from You, who preceded [shekidamta] the world. You could have sent one bolt of lightning and burned the Egyptians, but You did not do so; rather, You sent me to Pharaoh to request that he agree to free the Israelites in peace.

Alternatively, “from the wilderness of Kedemot” – I learned from the Torah, which preceded [shekadma] everything. When You came to give the Torah, it was revealed before You that the children of Esau and the children of Ketura would not accept it. Nevertheless, You sought to offer it to them so they would accept it. Therefore, “I sent messengers” [to offer them peace] (2:26).

The Holy One, blessed be He, said: You offer peace? I take an oath by your lives that you will inherit their land in peace, without casualties. <source>(Tanĥuma [Buber], Devarim) </source>

When the Israelites approached the territory of Sihon the Emorite, king of Heshbon, God promised Moses this land would be conquered easily, and He urged him to go out and wage war with him. Nevertheless, Moses dispatched emissaries in order to attempt to peacefully traverse Sihon’s territory. It was