Generally speaking as long as you are maintaining your status it doesn't matter if the visa is expired. So if you're in school with a valid I-20 you're fine. As are you dependents. If you have to travel outside of the US you will need to obtain a new visa to enter. I've certainly had cases where dependents did it at a different time than the principal beneficiary of the visa with no problem so I don't think that they would lose their status as long as you're re-entering with the same status.
A colleague can correct me if I'm wrong though.
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Carl Shusterman, Esq.
Former INS Trial Attorney (1976-82)
Board Certified Immigration Attorney (1986 - Present)
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(213) 394-4554 x0 Mr. Shusterman is a former INS Trial Attorney (1976-82) with over 35 years of immigration experience. His response to your question is general in nature, as not all the facts are known to him. You should retain an attorney experienced in immigration law to review all the facts in your case in order to receive advice specific to your case. Mr. Shusterman's statement above does not create an attorney/client relationship.
Ask your school DSO with respect to maintaining your legal status if still in school.
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