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If you enter under ESTA, you won't be able to work for the company and you will need to leave and reenter again in E-3 status to work for the company. And yes, if you recently have been in E-3 status and then seek to reenter under ESTA, you could have problems because CBP could conclude that you are coming to stay and/or work.

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Ok, actually the situation is following. We have some pilots with banks emerging in London where we need to work closely with them. I actually will go there and my wife will go to the US under visa waiver.

Seems like employment is going to be terminated at December 16, re-entry time - January 3.

Would there be any problems with this?

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