Travel during new H1b Counselor processing


H1aspirantVG

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Hi, I am currently in the US and working on F1 CPT that expires in Sept 2017 and I have to travel out of the US for family reasons in Late May 2017 so filing my new H1b under counselor  processing, Questions:

1. Can I enter the US on F1 in May if my H1b is processed/approved in the meantime

2. Can I get my visa stamped in Canada in Sept/Oct, do I have to finalize that now?

3. If H1b is approved, Can I put in a new change of status application from F1 to H1b after re entry in May 

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