B-2 Visa Extension - 2nd time

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My Father In Law and Mother In Law are visiting us and are due to go back to India mid April 2023. However, due to a medical emergency in the family they may have to apply for an extension of their B-2 visa. Can they apply for one now given they are scheduled to leave in two weeks (we missed the 45 day requirement). Also 12 yrs back we had a similar situation and got approval for their B-2 extension and they stayed for an additional six months. Does applying for a B-2 extension for the second time hamper their entry into the US in the future. Thank you

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