H1B Expiring soon, how late can i apply for extension.


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I am currently working and my H1B is expiring in few days (08/19/2017), what are the chances of getting H1 Extension approved if i apply before the expiry of H1B. I've got in to the situation believing that my H1 would be expiring in Oct 2017. Also please suggest what could be the repercussions of overstay after expiry. 


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