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H1 Transfer after leaving the country

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My company had filed for my Change of Status application to H1 from F1 - OPT - EAD.

My application got selected in the lottery and also has been approved. (waiting for physical confirmation mail)

I have plans to go back and work in India. However, I would like to keep my options open for a potential H1 transfer later on.

I would like to know what is the best time for me to go back to India.

Is it safe to go back to India around October 21st?

If I go back and work in India, since I would be "cap - exempt", I am assuming I would not have to go through the process of H1 lottery again. Am I right?

In case, in the future I would like to come back to the US, will just an H1 transfer suffice? Would the employers be willing to readily do it? What other documents would I need during that time?

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Thanks for your answer.
I have one more doubt in addition to the above question.
If I leave on October 21st for India, would it be advisable for me to get my passport stamped immediately as soon as I go to India?
(In case I plan to come back within the next three years)
Is it even possible for me to get my passport stamped for H1 because I will resign from my employer when I leave on October 21st?

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