Can I visit the USA as a VWP tourist immediately prior to entry on non-tourist visa?

Question

Here's my situation: I'm a UK citizen. I have an H-1B visa to work in the US as of 1 August. I also have a valid ESTA.

I would like to go to the US in July for a holiday, immediately prior to beginning my work. The holiday would be at the other end of the country from my work.

I can't enter with the H-1B as I can only enter the US on that visa 10 days prior to starting work.

Specific question: Would it be possible to visit the US in early July on the VWP, visit Canada/Mexico for a few days in late July, and re-enter the US with my H-1B visa?

General question: Is it possible to visit the US on the VWP, leave briefly, and re-enter on a different status (e.g. H, F, J, K, etc), without ever returning to one's home country?

I have posted this in Travel rather than Expatriates because, although in my specific case I have an H-1B visa, my question is more generally about VWP and travel, and I believe that it is applicable to travellers with non-immigrant visas.

There's a similar question here, although that's about going to the US and before having the H-1B visa.

Answer 1

The possible snag with that plan is that in order to enter as a VWP traveler by air, you're supposed to have a round-trip ticket whereby you will end up somewhere that is not Canada or Mexico.

Based on the anecdotal evidence available to us, this rule is not really enforced consistently. However, it does provide an impeccable ground for the border officer to deny you entry if he doesn't like the color of your shoes. And it is possible that the airline will refuse boarding you if you have neither a valid visa nor a round-trip ticket.

If you do attempt this plan, you should expect that the border officer will notice the future visa in your passport, and be prepared to convince him that (a) you're not going to start work before you're allowed to, and (b) you will actually make the visa run later, because the rules do not allow you to change from VWP to H-1B status while in the US. At the least, bring documentation of your job offer with its start date, and preferably also tickets for the short trip to Canada or Mexico.