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*After* you've received a plot-critical item from him, of course.
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Not necessary. He'll drop it, if you didn't get it before.
In my recent game, the Trynnies suddenly attacked me during a fight (and i *know* that i didn't hurt any of them before). Playing ironman, i continued (these Trynnies Spearman are *tough* for a low-level party). The shaman on the 6th bough was hostile too, but his drop contained the key.