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I switched my visa status to B1/B2 after leaving an H-1B job and have not yet found another. My change of status to B2 gave me six months, can I apply for an extension if I still need to stay in the US and then switch to H1B when I get an H1B job? Also is there a chance the extension would be denied or approved for a less than 6 month period?

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can I apply for an extension if I still need to stay in the US

Yes. There is no limit to the number of B2 changes of status or extension of stay you can be granted.

and then switch to H1B when I get an H1B job?

Yes, the company can request Change of Status when applying for the H1b petition.

Also is there a chance the extension would be denied or approved for a less than 6 month period?

Yes.

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