In general, the point of the "after death" canonpoint for inmates is tied into the idea of the barge being a "Last chance." Since Joshua seems pretty comfy/in control of his afterlife, for him to get snapped up by the barge, it would probably be best for him to suffer Erasure somehow. You can headcanon a post-canon Erasure or use any moment when he had a very close call that could have resulted in erasure if things had been a little different (this can be the fakeout you mentioned, if that fits the bill, or any other time that he had a high risk of Erasure and a slightly AU would make his death plausible).
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In general, the point of the "after death" canonpoint for inmates is tied into the idea of the barge being a "Last chance." Since Joshua seems pretty comfy/in control of his afterlife, for him to get snapped up by the barge, it would probably be best for him to suffer Erasure somehow. You can headcanon a post-canon Erasure or use any moment when he had a very close call that could have resulted in erasure if things had been a little different (this can be the fakeout you mentioned, if that fits the bill, or any other time that he had a high risk of Erasure and a slightly AU would make his death plausible).