Mapping the boundaries of the Promised Land reveals a complex and dynamic geographic path. Rather than stretching in simple straight lines, the boundary constantly curves, shifts, and adapts to the landscape. While identifying these precise ancient landmarks today is nearly impossible and relies mostly on guesswork [רש״ר הירש], the detailed journey of the border reflects a deeply purposeful design. In fact, a conceptual view suggests that these exact, winding boundaries were decreed and set in place at the very creation of the world [שפתי כהן].
As the frontier travels from the south [ביאור שטיינזלץ] toward the Ascent of Akrabbim, its shape frequently changes. In certain areas, the boundary protrudes and bends outward, creating an uneven, turning edge [רש״י, רשב״ם]. In other sections, the border cuts a perfectly straight path without any detours [רשב״ם], sometimes even passing directly through the middle of a city [שפתי חכמים]. The route then pushes forward until it reaches the Wilderness of Zin [שד״ל, רש״י, שפתי חכמים], with the far edges of the boundary continuing to extend outward into the distance [רש״י, ביאור שטיינזלץ].
The exact navigation of this expanding border sparked a complex geographic debate. While some maintain that the boundary moves forward in a continuous straight line [רשב״ם], others map a much more intricate route. According to [רש״י], the border widens and curves diagonally toward the northwest, spreads out toward Hazar-addar, and then retracts as it turns back south. Later scholars [גור אריה, משכיל לדוד, דברי דוד, שפתי חכמים] engaged in extensive discussions to decipher this precise mapping, debating whether these specific northern and southern curves ultimately expanded the territory of the Land of Israel or reduced its size in favor of the surrounding nations.
As the border reaches Kadesh-barnea, a significant historical difficulty arises. Moses famously sent the spies from Kadesh-barnea, yet he never crossed into the Promised Land. If Kadesh-barnea is located within the borders of Canaan, it would imply that Moses actually entered the land. To resolve this, the primary approach among commentators [פענח רזא, דעת זקנים, בכור שור, חזקוני, חומת אנך, הדר זקנים] is that there were actually two completely different locations sharing the name Kadesh-barnea, just as there were two places known as Mount Hor. One was situated in the wilderness across the Jordan where the spies were dispatched, while the other was a distinct district located on the very edge of Canaan. Alternatively, another perspective suggests that the border was simply extended slightly south toward the territory of Edom in order to straighten the overall line of measurement [בכור שור].