H1B Extension - how soon and when ?


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My current H1B expires in October of this year. I heard employer can file 6 months before expiration. If my H1B extension gets filed in the month of May (5 month before expiration) in premium and gets denied for some reason, still I can file another extension since my original  H1B is not expired yet ( expires in October 2016)?


Please advice. Thanks. 

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