Joshua 5:2-9At that time the LORD said to Joshua, “Make flint knives for yourself, and circumcise the sons of Israel again the second time.” So Joshua made flint knives for himself, and circumcised the sons of Israel at the hill of the foreskins. And this is the reason why Joshua circumcised them: All the people who came out of Egypt who were males, all the men of war, had died in the wilderness on the way, after they had come out of Egypt. For all the people who came out had been circumcised, but all the people born in the wilderness, on the way as they came out of Egypt, had not been circumcised. For the children of Israel walked forty years in the wilderness, till all the people who were men of war, who came out of Egypt, were consumed, because they did not obey the voice of the LORD—to whom the LORD swore that He would not show them the land which the LORD had sworn to their fathers that He would give us, “a land flowing with milk and honey.” Then Joshua circumcised their sons whom He raised up in their place; for they were uncircumcised, because they had not been circumcised on the way.
So it was, when they had finished circumcising all the people, that they stayed in their places in the camp till they were healed. Then the LORD said to Joshua, “This day I have rolled away the reproach of Egypt from you.” Therefore the name of the place is called Gilgal to this day.
At the outset of the Holy War, the people of Israel have to become holy. Their reproach has to be rolled away through the rolling away of the flesh.
They then proceed to roll away Jericho, as they march around the city until its outer covering falls off.
In the new covenant we are given instructions to make the world holy. We roll away its reproach through the new sign of sanctification, baptism.
Matthew 28: 18-20
And Jesus came and spoke to them, saying, “All authority has been given to Me in heaven and on earth. Go therefore and make disciples of all the nations, baptizing them in the name of the Father and of the Son and of the Holy Spirit, teaching them to observe all things that I have commanded you; and lo, I am with you always, even to the end of the age.” Amen.
(James Jordan originally pointed out the connection between the circumcision of the people at Gilgal and the circumcision of the city at Jericho. His lectures on this can be found in his Numbers through Judges Survey at the Auburn Ave. media site.)