OPT to H1 transfer


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I am currently working on OPT for Company A. My H1 petition filed by another company B was approved and the change of status is effective October 1, 2017. I have not worked for Company B  

I want to continue to work for Company A and they are agreeable to file for H1 transfer. Company B is fine too. 

My question is - which of the following options is preferred from approval risk standpoint. 

1. Apply for H1 transfer before October 1st and continue to work for Company A 

2. Apply for transfer post October 1st - change to company B from October 1st on H1 and then apply for H1 transfer to Company A. 

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