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If you want to attack Illaoi you'll need to get past the barrage of tentacles to do anything. If you don't have the will sufficient to pass the test, Nagakabouros will end you regardless of if Illaoi is still standing.
Even if he attacks and somehow kills Illaoi that wouldnt be considered 'passing' more along the lines of trying to cheat the test by ending it by killing the one giving it, which would get him erased
I don't see that in the ability (because it's not described or shown to be like that) but assuming it's wrapped around, Sticky Fingers can easily unzip his own arms and kick them towards Illaoi who's right in front of him.
Him attacking Illaoi is him persuing his goals and ambitions in life regardless of whatever challenges stand in his way. That's absolutely passing the test. And furthermore there's nothing saying you can't do that or you'll fail.
"He screamed as his soul was ripped from his body. His doppelganger stood unmoving before Illaoi. The spirit of Gangplank smoldered an almost blinding blue, its body crackling and flickering through his previous lives. The mass of tentacles attacked the wounded captain. Gangplank rolled and stumbled to his feet, dodging what he could. But for each one that missed, more and more appeared. Reality twisted and churned around him. The swarm of tentacles crashed against him, pushing him down, pulling him further and further from his soul—toward oblivion."
No, him attacking Illaoi would be perceived as trying to cheat the test. He'd have to complete the test first before attacking Illaoi if he doesnt want to get insta-erased by Cthulu's daughter. And even if he does kill Illaoi and isnt instantly erased as a result the Test would still continue.
Also considering spirits get instantly erased by Naga, there is actualyl a good chance that Stick Fingers would just get instakilled the second Illaoi begins the test
What you're bolding doesn't answer my questions. Gangplank not being able to command or control his doppelganger doesn't imply his doppelganger is being restrained - he just lacks the ability to command or move his spirit. Bruno has said ability. Furthermore in game, the spirit remains unrestrained, it just stands still. Again though, Bruno is able to command and move his Stand so there's no reason to suggest that Illaoi has power nullification of some sort and that he wouldn't be able to do so.
Sticky Fingers isn't a spirit, it's Bruno's manifestation of soul so no, there's no reason for Naga to instantly erase him (not like you sourced it or anything either).
So to summarize so far:
> Illaoi is extremely likely to use test of spirit to pull Bruno's soul directly in-front of her.
> As seen with Giorno and Black Sabbath, Bruno is able to replace/defend his soul with his Stand if it is pulled from his body.
> Sticky Fingers is now directly in-front of Illaoi and is able to be controlled by Bruno, whom would certainly have him feed her a barrage of punches which would turn her into a pile of limbs and digits.
> Bruno is very likely to survive the test of spirit as his entire character and personality does not contradict (and in fact, supports) the ideology of Naga K or Illaoi