Having been through the system I can probably guess what he did wrong. F1 status requires that you show no intent to stay. If he had declared that Microsoft was

Having been through the system I can probably guess what he did wrong. F1 status requires that you show no intent to stay. If he had declared that Microsoft was sponsoring an H1B prior to re-entry and we as attempting to enter with a F1, then he broke the F1 rules. If you break any rules you are pretty much SOL.