[Answer] Against what small city did Israel lose its first battle in Canaan?

Step 1 : Introduction to the question "Against what small city did Israel lose its first battle in Canaan?"

...Fresh off their Jericho victory, Joshua and Israel's warriors were assured they'd be victorious against the much smaller Canaanite city of Ai. It came as a shock, then, when Ai overcame them, killing 36 of their soldiers and sending them fleeing into the hills. The defeat was so devastating for them that "the hearts of the people melted and became as water." They knew if God did not fight for them, there was no way they could win. God had warned Israel before the battle: Do not take any item from the pagan enemy. God told Joshua He would not stand with Israel if this happened, nor would the land inhabitants fear Israel, knowing their "god's" items resided in Israel's camp. After going from tribe to tribe, Joshua found the culprit with the stolen items, Achan, and dealt swift justice. When the Israelites next met the soldiers of Ai, they were able to overcome the city with the help of God.

Step 2 : Answer to the question "Against what small city did Israel lose its first battle in Canaan?"

Ai:

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