יהושע, פרק ה׳, פסוק ו׳

The journey of the Israelites through the desert lasted forty years following the sin of the spies. During this time, the entire generation that left Egypt passed away, making room for a new generation destined to enter the Promised Land. The older generation, comprised of the men of war who departed from Egypt, had failed to listen to God. As a result, God swore that they would not live to see the land [מצודת דוד, ביאור שטיינזלץ].

Throughout those decades of wandering, the new generation of sons remained uncircumcised. The primary reason for this was the reality of their constant travel, which caused physical weakness and provided a practical excuse to delay fulfilling the commandment [מלבי״ם, אלשיך]. However, some maintain that had this generation been entirely righteous, much like the tribe of Levi, they would not have relied on this excuse to avoid the obligation [מלבי״ם]. Another practical challenge was the steady passing of the older generation, which meant there were no longer enough worthy, circumcised men fit to perform the procedure on the rest of the nation [מצודת דוד].

Joshua, who belonged to the older generation by age but was spared from the decree of death in the desert, stepped in to correct this national deficiency. Because the sons were raised up in place of their fathers to inherit the land, the act of Joshua circumcising them is viewed as though he had spiritually repaired the generation of the fathers themselves. Furthermore, there was a distinct physical difference between the generations. The fathers had been circumcised but lacked the final step of the procedure, whereas the sons were completely uncircumcised. Recognizing their vulnerable state, God showed them mercy and commanded that they be circumcised at this moment [אלשיך].

God promised to give the land to the new generation based on an oath He made to their forefathers. He granted the land to the founders of the nation so that, even if their descendants lacked personal merit, they would still receive the territory by virtue of their ancestors. Knowing in advance that the generation leaving Egypt would not enter, God gave it to them strictly as an inheritance to pass down, rather than a territory to possess themselves. Therefore, the oath was made to the fathers, but the actual giving of the land was directed to the generation of the sons who finally entered it [צוארי שלל, חומת אנך]. This destination was characterized by its flowing milk and honey, a description highlighting its sheer abundance and natural capacity to overflow with rich resources [מצודת ציון].