While the other Canaanite kings united for open war against the Israelites, the Gibeonites chose a completely different survival strategy based on diplomacy and deception. The primary approach among commentators is that their actions are directly compared to those of the other Canaanite kings. Just as the surrounding nations took steps to save themselves, the Gibeonites did as well, though they opted for cunning rather than combat [רלב״ג, מלבי״ם, ביאור שטיינזלץ]. Others suggest their deception mirrored the military tactics the Israelites themselves had recently used to conquer Jericho and Ai [מצודת דוד, רד״ק]. A particularly ironic historical view links their strategy back to the story of Dinah and Shechem. Since the Gibeonites belonged to the Hivite nation, they were acting with the same deceit that the sons of Jacob had once used against their Hivite ancestors [רש״י, רד״ק]. Furthermore, this trickery was necessary because the Gibeonites only decided to surrender after hearing of the Israelite victories, making a standard, peaceful surrender impossible at that late stage [אלשיך].
To execute their plan, they needed a convincing cover. The vast majority of commentators explains that they disguised themselves as official political ambassadors arriving from a distant land [רש״י, מצודות, רלב״ג, רד״ק]. These were not mere messengers, but formal representatives sent specifically to secure an agreement and return with an answer for their leaders [מלבי״ם]. Another approach suggests they physically altered and disguised their personal appearance [ביאור שטיינזלץ]. Conversely, some commentators note an ancient tradition indicating they simply gathered provisions and equipped themselves for a journey [רד״ק, מנחת שי, אלשיך].
To solidify the illusion of a long and exhausting expedition, they loaded their donkeys with sacks that were rotting, worn out, and frayed from heavy use [רש״י, מצודת ציון, ביאור שטיינזלץ]. They also brought along leather wineskins [מצודת ציון, ביאור שטיינזלץ]. To further amplify the appearance of traveling a great distance, these leather pouches were not only worn but severely cracked and torn. They were tied shut around the tears to prevent the wine from spilling [מצודות, ביאור שטיינזלץ]. This meticulous attention to every small detail of their gear was designed to trick the Israelites into believing these envoys had truly traveled from the edge of the world, resulting in equipment that was completely ruined along the way [מצודת דוד, מלבי״ם].