I have worked in H1B status for 4 years, but am now changing to F-1 status to get a degree in a completely different field.
After graduating, would I then need to go through the lottery again to return to H1B?
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You can re-use your same H1B again after you complete your F1 study. You would still have 2 years left from the total 6 years of H1B quota.
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You would not need to go through lottery again.
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The only caveat is that if your new job (in the area of new F1 qualification) may or may not be eligible for H1B. I mean if it does not fit the H1B Visa criteria, it may be rejected.