The sons of Anak are first mentioned in . The Israelite leader Moses sends twelve spies representing the Twelve Tribes of Israel to scout out the land of Canaan. The spies enter from the Negev desert and journey northward through the Judaean hills until they arrive at the brook of Eshcol near Hebron, where reside the sons of Anak: Sheshai, Ahiman, and Talmai. After the scouts have explored the entire land, they bring back samples of the fruit of the land; most notably a gigantic cluster of grapes which requires two men to carry it on a pole between them. The scouts then report to Moses and the congregation, that "the land indeed is a land flowing with milk and honey". However, in , ten of the twelve spies state that the inhabitants of the land are descended from the Nephilim, discouraging the Israelites from even attempting to possess the land. They reported that the men were taller and stronger than the Israelites, and that they felt like grasshoppers in their presence. However, the faithful spies Caleb and Joshua do not verify this report, leading some scholars to believe that the fearful reports from the other ten are hyperbolic and should not be taken literally.
