Can I enter the United States on a Visa Waiver, go to Mexico and re-enter with an F1 visa?

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Buy a fully-refundable return (or onward) ticket and cancel it after entering the US.

Having entered the US under the VWP, it is perfectly fine to exit to Mexico and re-enter in F1 status.

Your main concern will be convincing the officer on your first entry that you will be a genuine tourist for the two months preceding your studies (have documents proving your plans as clearly as possible).

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