At a critical breaking point following the sin of the spies, the path forward to the Promised Land is abruptly sealed. The decree of wandering forces the Israelites into a complete reversal, demanding they retreat from the border and head back into the deep desert. The explicit mention of the Amalekites and Canaanites positioned along the way serves a specific purpose. The primary approach among commentators is that this acts as a severe warning: if the people attempt to advance and enter the land, the enemy will slaughter them, as God has removed His protection and will not accompany them into battle [רש״י, ביאור יש״ר, אבן עזרא, שטיינזלץ, מזרחי]. This fatal danger exists only if they rebel against God's command to retreat; as long as they step back, they remain entirely safe [גור אריה].
Other perspectives highlight a psychological dynamic of measure for measure. Because the Israelites were consumed by profound panic upon hearing the spies' reports about Amalek, they demonstrated that they were unworthy of fighting them [שד״ל]. Consequently, God leverages their own fear, invoking the impending threat of Amalek to deter any forward movement and compel their retreat [שפתי כהן, בכור שור, חזקוני]. Furthermore, sin itself creates vulnerability. Wherever sin is present, Amalek gains the power to dominate [אלשיך]. Having sinned, the Israelites are stripped of their defenses and cannot even linger in their current encampment without falling prey to the enemy's hostility [אור החיים]. In this context, the Canaanite presence actually refers to the Amorites, serving as a collective identity for the various regional nations that had formed an alliance against them [אבן עזרא, חזקוני, ביאור יש״ר].
A geographical discrepancy arises regarding the enemy's location, initially described as sitting in the valley, yet later noted as occupying the mountain. Commentators resolve this by suggesting a military ambush tactic. The enemy forces may have originally encamped in the valley, but upon hearing of the Israelites' approach, they ascended the mountain to lay a trap [דעת זקנים, חזקוני]. Alternatively, they may have gathered on the mountain and descended to ambush the Israelites in the valley below [הטור הארוך, אבן עזרא]. Another possibility is a massive, widespread deployment, where the enemy spread their troops across all borders, occupying both the mountain and the valley to block every possible route [ביאור יש״ר], or that their main camp was in the valley while a smaller combat unit held the high ground [חזקוני]. A more geographic solution suggests that the valley actually describes the lower slope of the mountain itself, meaning both descriptions refer to the exact same terrain [הכתב והקבלה].
Facing this looming threat, the Israelites receive the command to turn away the following day. This timeframe does not necessarily dictate the exact next day, but rather points to an unspecified future time, as it is known the nation remained in Kadesh for many days [חזקוני]. The command underscores that God does not want them to establish a permanent settlement in the desert; they must continue moving so the next generation can eventually enter the land [העמק דבר]. Conversely, the delay might emphasize that the current day is marked by divine anger, necessitating that the journey begin later [שפתי כהן]. The instruction to turn means a literal pivot backward [רש״י, שפתי חכמים, ביאור יש״ר, מזרחי], symbolizing the tragic, final closure of this generation's opportunity to enter the land. Yet, the directive to journey is ultimately for their own good and benefit [ברכת אשר על התורה], even though it initiates a punitive wandering. They are ordered toward the wilderness by way of the Red Sea. This does not mean they will cross the sea again, but rather that they must march along a familiar route known as the way of the Red Sea, leading them away from the Promised Land and back into the depths of the desert from which they came [ברכת אשר על התורה, שפתי חכמים, מזרחי].