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I have a work contract with a US company and, for that reason, I can't stay in the US for more than couple of days since I need to work. Working while in the country would violate my visa and Federal law under which the company employs me. I would risk being banned from entering the country which would heavily affect my future professional life.

However, during the summer I travel almost every week from the EU to the US to attend conferences as a visitor. This is not a paid activity and I don't perform work while visiting. I can enter the US as many times as I am permitted, when I have a valid reason to go there.

This is very time consuming. Therefore, I thought I should apply for a Canadian ETA, and find a temporary accommodation in Canada, and travel back and forth to the US. It would reduce my travel from 20 hours to just 2 hours, and eliminate jet lag. I can enter both countries and I can work for foreign company while being in Canada, in both cases without problems as long as I don't overstay and get caught. It is not clear whether I could travel frequently between the US and Canada without issues.

The biggest issue I think could be the Canadian border as it would be perhaps hard to explain why do I need to come and return each week from US other than to shorter my travel times.

As I understand it, this would be perfectly legal. It's just 2 hours to fly from Montreal to NYC and the cost of travel is equivalent to the price of temporary accommodation in Canada.

I will contact both the Canadian and US border agencies for their opinion but it just occurred to me that I may wrong and this would be a problem.

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    what makes you think Canada is cool with you working for the US company while you're there? – Kate Gregory Mar 10 '17 at 2:24
  • One of my contracted clients. I have at least 10 clients all over the world. Not in Canada, do. Generally they can not claim that working for clients in US or China is a problem while entering Canada. They could argue that doing so can mean that I could stay in Canada for 20 years as I have the means to support myself financially without the need to take employment locally. But they could say that about an individual with big financial savings. If there is a clear intention to leave the country withing the period of approved stay what would be the problem? – user58464 Mar 10 '17 at 4:06
  • Many countries, I believe including Canada, have rules against performing work in the country when present as a visitor. It does not matter that the clients are outside Canada. An individual with savings is not performing work, of course; that is the crucial difference. – phoog Mar 10 '17 at 4:16
  • @phoog sure they do but you need to check the definition of "work". There's a surprise. – chx Mar 10 '17 at 4:51
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    Note that if you're admitted to the US under the Visa Waiver Program, your trips back to Canada won't reset or pause the clock on your 90-day admission to the US. You'd need to leave North America for that to happen. – Zach Lipton Mar 10 '17 at 4:52
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Here's what the Immigration, Refugees and Citizenship Canada says about What kind of activities are not considered to be “work”?:

long distance (by telephone or internet) work done by a temporary resident whose employer is outside Canada and who is remunerated from outside Canada;

In Canadian terminology, "temporary residents include visitors, students, workers and temporary resident permit holders" (source).

This is you. What you do is not considered to be work. Welcome to Canada and enjoy your stay!

  • This answer doesn't address whether US immigration will be happy with this scheme (IMO, they won't). Also, as a contractor, is it true that the asker's "employer is outside Canada"? – David Richerby Mar 10 '17 at 13:13
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    @DavidRicherby the US border guard is concerned by whether OP's travel pattern shows he is living (or attempting to live) in the USA. His stay in Canada is, as far as I am aware, no concern of theirs. If he shows conference tickets that looks like a valid thing to me. But this is more of a subjective matter hence this is a comment and not an answer. Especially if OP is going to travel to different places and not just NYC he should be just fine. I think so at least. I barely dare to mention the color of his skin might play a role too. – chx Mar 10 '17 at 13:37
  • @chx It is IMO likely that the US will think that travelling multiple times between the US and Canada is materially different from travelling multiple times between one's home country and the US: the fact that Canada doesn't reset the "VWP clock" shows that Canada is different. The scheme is an attempt to live between the US and Canada for an extended period; I'm not confident that the US would want to participate in that. – David Richerby Mar 10 '17 at 13:48
  • I agree that this appears to be entirely legal. One thing I think you will need to consider is what to answer when the Canadian border guy asks "What is your reason for coming to Canada?". "So that I can work between visits to the US" might be problematic, but something like " want to make a series of visits to the US and use Canada as a base" is probably OK. – DJClayworth Mar 10 '17 at 13:55
  • @DJClayworth "I want to make a series of visits to the US and use Canada as a base." "Why can't you just stay in the US the whole time?" "Because, er... *mumble* I want to work." – David Richerby Mar 10 '17 at 15:22
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De jure there are dozens of complex laws and regulations regarding remote employment, under which you may or may not be violating the conditions of your visa by working remotely for your US employer while visiting the US. Canada might also have laws against remote employment, although @chx seems to provide a quote stating the opposite.

De facto, as long as you don't mention your remote job to immigration personnel at the airport/land crossing, there's a 99.99% chance no one will ever find out. There are millions of people breaking the law by being employed at on-site jobs in the USA, so digital nomads are a pretty low priority for law enforcement. It would probably be even more suspicious to keep traveling from Canada every week, rather than coming for long periods of time to visit the conferences.

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    "Screw it, just enter illegally and hope for the best" is a really, really bad answer. – David Richerby Mar 10 '17 at 12:54
  • @DavidRicherby no, the answer is not to mention the US client. Say you're an independent contractor (which is probably true) and get the entry stamp. – JonathanReez Mar 10 '17 at 12:55
  • The asker will be asked why they want to visit the US for what seems to be quite a long time. Their answer is that they're going to a sequence of business conferences and it would be too time-consuming to travel backwards and forwards. This establishes that there are gaps betwene the conferences. So what is the asker going to do in those gaps? They can't work remotely, because that's working and working is illegal. So now they need to explain how their employer is OK with them taking so much time off. IMO this will look highly suspicious to an immigration officer. – David Richerby Mar 10 '17 at 13:01
  • @DavidRicherby as an independent contractor you have a lot more leeway. You might as well say you're taking time between contracts to visit the conferences and improve your knowledge. Also conferences don't necessarily have pauses - you might need time for reading the papers, talking to new contacts, preparing your own presentations, etc. – JonathanReez Mar 10 '17 at 13:03
  • @DavidRicherby "what is the asker going to do in those gaps?": go to Canada. Why would the US care about that? "They can't work remotely, because that's working and working is illegal": but the plan is to go to Canada to work remotely, where working remotely as a visitor is apparently not illegal. I fail to see the problem. – phoog Mar 10 '17 at 15:27

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