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Say, for example, I had a student visa that allowed me to stay in America from September to February. Would I then be able to come in August on a Visa Waiver to America, and then when September comes around, would it then just switch over automatically to my student visa as I begin my school, without leaving the country?

Or would I have to leave the country and then come back to begin my stay as approved by my student visa? I would like to visit some family before I start school, but don't know if I am able to use the Visa Waiver for that stay.

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    ESTA isn't a visa, it's a travel authorisation - you would enter the country under any visa waiver program the US offers your countries passport holders. You need an ESTA to travel to the US by certain methods (fly, certain train routes, sometimes by sea), but when you get there the ESTAs job is done and you still have to be granted permission to enter by CBP under separate rules.
    – Moo
    Apr 7 '18 at 8:08
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No, for a couple of reasons. The first is that status doesn't change automatically; you have to apply and pay a fee of a few hundred dollars.

The second is that VWP visitors are generally ineligible to file change-of-status applications. Instead, you have two options:

  1. Arrive no earlier than 30 days before the start of your program and enter using your student visa.

  2. Arrive earlier than 30 days before the start of your program, enter using the VWP, leave the country, and reenter (no more than 30 days before your program starts) using your student visa.

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