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If he is in his initial school and not an additional upgrade school, then a separation is very likely. Prior to graduation, if someone is presenting problems both academically and through misconduct, it doesn't really give a lot of confidence in their military future. During military training, we have the most restriction and least freedoms. Individuals that still get into trouble during those phases tend to get into much more trouble when they have the full freedom of regular military service.
Commanders have a lot of discretion, so there is no knowing exactly what will happen. He certainly could be retained, but separation is not difficult to accomplish at all and it is definitely possible.
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