The three-sided conflict for Outbound Flight involved Outbound Flight, Picket Force Two, and the Vagaari fleet. This clash resulted in the deaths of almost everyone aboard Outbound Flight and the majority of the Vagaari's ships. This outcome successfully achieved Darth Sidious' initial goal. The survivors from the Outbound Flight Colony later referred to this battle as the Devastation.
Force Commander Mitth'raw'nuruodo's Picket Force Two lay in wait along Outbound Flight's projected path, situated between the Geroon homeworld and Crustai. Utilizing the Whirlwind's gravity well projector, Outbound Flight was forcibly extracted from hyperspace. Thrawn attempted to negotiate with the disgraced Jedi Master Jorus C'baoth, urging him to either return to the Galactic Republic or alter course, as their current trajectory led towards the rumored location of the Yuuzhan Vong. C'baoth's refusal compelled Thrawn to maintain Outbound Flight's entrapment.
Simultaneously, Jorj Car'das approached the Vagaari fleet to persuade them to assault Crustai. He accomplished this by gifting them battle droids and droidekas. Unbeknownst to both Car'das and the Vagaari, Thrawn had programmed the droids to eliminate the Vagaari crew upon his command. The Vagaari then mobilized their entire fleet, only to be intercepted and pulled from hyperspace as well.
The Vagaari initiated the engagement by transmitting aggressive messages, prompting the Jedi to use the Force to paralyze their entire fleet. Thrawn seized this opportunity to deploy droid starfighters against the Vagaari, and to activate the "gifted" battle droids to eliminate the Miskara. The droid starfighters attacked at close range, penetrating the Vagaari's living shields and damaging their hulls.
The deaths of thousands of Vagaari weakened the Jedi's concentration. Thrawn then commanded his forces to target Outbound Flight, specifically aiming for the weapons blisters and shield generators, while leaving the rest of the vessel untouched. Tragically, this resulted in the deaths of most of the Jedi, who were operating the weapons systems at the time. Thrawn renewed his request for Outbound Flight to return home, but Jorus C'baoth instead succumbed to the dark side and began to choke Thrawn. As the Chiss struggled against C'baoth's assault, Kinman Doriana activated a switch, altering the droid starfighters' programming. The droids ceased their attack on the Vagaari and instead rammed into Outbound Flight, breaching its hull and exposing it to the vacuum of space. Ten pairs of fighters, equipped with radiation bombs, detonated within Outbound Flight, killing almost everyone, including C'baoth. The remaining Vagaari ships, now free from attack, retreated from the area and jumped into hyperspace.
Darth Sidious's primary goal of destroying Outbound Flight was realized, albeit through unforeseen circumstances. Thrawn would later lament the outcome, regretting the unnecessary deaths of civilians and the escape of the Vagaari. Three hours later, a Chiss fleet under the command of the Fifth Ruling Family, led by Aristocra Chaf'orm'bintrano, arrived to seize control of the Vagaari fleet (and subsequently Outbound Flight). A series of diversions and delays enabled Lorana Jinzler and Mitth'ras'safis, Thrawn's brother, to escape with Outbound Flight, thereby preventing a critical destabilization of Chiss society.
In addition to losing his brother, many within the Ruling Families still viewed Thrawn's actions as tantamount to murder. Although Thrawn managed to persuade the Ruling Families to retain his position in the fleet during a meeting on Chiss Ascendancy's capital planet of Csilla, his actions were subjected to intense scrutiny from that point forward.