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Specific/Extended Question

What legally counts as working in the States while living there (technically vacationing) while visiting for the legal vacation period that a Canadian passport allows.

For example, would freelancing as a Canadian on an freelance website, would working remotely for a Canadian company, would working remotely as a Consultant in Canada, how about consulting as a Canadian Company to american companies? This is obviously a spectrum of entering the american market ending with selling services directly to Americans as a Canadian while filing business taxes and income tax in Canada.

My Relevant Background Knowledge

I know that while staying in the US on a passport you cannot stay more then 6 months before needing to either apply for an extended stay or returning to Canada.

I don't know much about what else would be restricted while 'vacationing' in the US.

Reason for the question

I am a computer scientist, my current job can be (and is) done remotely.It is very easy to do jobs remotely in general either as a freelancer or simply accepting a remote job.

There are two reasons I'm interested in this. One is extended vacations and the other is a romantic interest I have in MD, USA.

Additional Personal Background

I previously lived in the states for four years due to my father being on exchange from the Canadian to US military. So I had a student visa and some form of diplomatic dependent status at the time (green passport).

I know you need a Visa to work in the states, but with the internet it seems plausible to legally work in Canada while residing in the states. I'm unsure of what would be considered working in the states though in such an online environment. For example I currently do some work that is technically consulting and am my own business. If I run a consulting business (just me) from Canada and targeted american clients that would seem to me definitely bad faith, but technically working in Canada.

Currently I am finishing my Bachelors of Computer Science in Canada so it is feasible that I could get a work Visa. I may be able to go work in the states through an exchange program as an intern as well this coming summer. After school I would like to go through the (I hear lengthy) Visa process while technically vacationing in the states and still making money working in Canada. This would be ideal in terms of discovering if my romantic interest is going to be something permanent giving me somewhat of a trial period. I realize marrying is a common way for people to become american citizens, but in my case I'm only interested in being an american if/while things work for me romantically.

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    Hi, welcome. You might want to ask this on Expatriates. As I understand it, the US does consider that visitors are not allowed to work remotely for foreign employers. If when you enter you say you're planning to stay for six months, and they ask how you're going to pay for it, and you say "work remotely for my Canadian employer," I believe they will refuse entry. Canada notably has the opposite policy, but it seems to be a rare exception. In addition to the immigration considerations, there are tax considerations. – phoog Sep 20 '18 at 15:54

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