For USCIS to change your status, you must be in valid status on September 30th. Otherwise, you need to apply for an H-1B visa stamp abroad.
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A noncitizen can hold multiple visa stamps in his or her passport and use those in accordance with the purpose of a particular trip. A noncitizen can only be in one status at the time.
A noncitizen cannot change status unless the status from which the change is sought is valid on the day when the change of status application is filed.
The last action rule applies unless additional H1B employment is claimed instead of change of status. This is why it is always dangerous to file multiple petitions at the same time.
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You may have one one status at a time.
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