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Laidoff: 60 day grace period ending soon. Few questions

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I got laid off July 05 2017 and my 60 days grace period ends 3rd of September. I have couple of questions:

1. What is the latest date I need to find an employer and file for a H1B transfer in order to avoid leaving the country? I assume the LCA takes around 1 week. Can I continue to stay as soon as I apply for LCA or H1b transfer?

2. In case if I decide to overstay 1 or 2 months after the grace period, just to give it a last try or to settle things, what's the worst that could happen? I know couple of my friends did that and had no problems. Some stayed for at least 4-5 months. 
3. If I find an employer after the 60 days grace period and file for H1b transfer, while I am still staying in the country, what kind of problems would there be?
Is there anything else I should know given my situation?
I would appreciate any feedback.
Thank you

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An H1 petition has to be filed within the 60 days.

What happened to other people who stayed longer has no bearing on what can happen to you. Times change. The current administration is less forgiving than earlier administrations, for example.


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