Telecommuting to Canada while a Visitor in the States?

Title about sums it up, but some details.

I'm a student here in London, Ontario (citizen, have lived here all my life). I'm currently between semesters. I met my American girlfriend in January of last year on OkCupid. never meant to do the long distance thing again but it's weird the way things turn out.

I'm also a web developer, self-employed. I have a couple main clients right now, one of which is right here in London. I contract out to people on a project basis, and due to the nature of my work, I don't need to be in a specific location to do it, I just need my laptop and internet access (and even my laptop is negotiable as long as I can install software).

US Customs takes an interest in me, having refused entry to me in the past (about two and a half years ago now) for not showing sufficient ties to Canada (they gave me a checklist of stuff to give them; I came back a week later and they let me in on an I94 but there seems to be some sort of flag on me in their system now). I haven't had any real issues with crossing recently, and I'm always honest with them.

Here's my question. I've told US Customs I'm self-employed. Last time I crossed, the officer asked if I was taking a two week vacation, and while he let me in, he was typing furiously on what I assume is my fairly lengthy US entry profile on the USCPB system. I want to be with my girlfriend for as long as possible this summer, as when school starts again I'll have to be here (obviously). What would US customs say if I told them that I wanted to telecommute to my London client while a visitor in the States?

I figure if they have no problem with this idea, it accounts for any money issues they might have with me being in the States, and that seems to be a major thing with visitors in proving that we're not going to stay (they've at least twice asked how much money I had, both on-hand and in my bank account). Thus far I've told them I've not been working at all (which is pretty much true as there was a lull between projects), but if I tell them that for the rest of the summer, eventually someone's going to get suspicious, and obviously I have to work so I can pay bills, etc.

Any ideas? I'm not planning on immigrating (yet) and fully intend to return in September for school, and if necessary I can break the trips up into smaller segments.

Upon further reading here, it seems that no visa would fit this category and it's illegal to do so otherwise. Is there really no way to do this legally? Does this just leave me with taking ~$250 per week (or proof thereof) with me when I go? And wouldn't this trip suspicion if I did it long enough, since they'd wonder where the money was coming from?

Where are your clients? Are they all in Canada? If all your clients are in Canada and you're paid in Canada then it's not a tremendously big deal. Technically it is illegal but given that you are the only person who knows you are working there and there's this thing called the fifth amendment there isn't much USCIS can do it about it.

If you want to do it legally you have to set up an office, go in on an E-1 visa (assuming you have a US client) do a small mountain of tax paperwork (get an EIN, do withholding, etc.) bill people from the US address and so on.

If they require you to have an I-94 that does make it more complicated because they will know when you leave, so that might flag something up if you go back into the US later on. If you told them you were going to be there for a couple of weeks and then you stayed for months, they might figure that out.

Thanks. They've only required me to have an I-94 once, and that was in 2005 when I came back a week after they'd sent me back to Canada, with all the paperwork they required. Getting in this time was rather easy, actually (I came back on Sunday); I think a lot depends on the agent to whom you speak.

Out of curiosity, outside of them issuing an I-94, does USCBP have access to Canadian entry records from the US? I know there's a lot of sharing of data that goes on these days.

I do have one client here in the States right now, but I haven't heard from them in a while; most of my work is from the London, ON client. I wish the laws would catch up with the technology though. Anyway, at least if and when I do want to move down here I'll have a few options, between transferring to a school here on a study visa and trying for a K visa if I propose or something. It would just be nice if I had a solid way to telecommute while I was down here as a visitor.

They are going to share data but it's not fully set up yet. How far they've gotten with it I don't know, apparently major airports do have the information now.

Coincidentally I was just talking to someone today who was telling me there is a stink about giving USCIS access to CPIC. US law enforcement agencies have access to CPIC so they're aware of your criminal record but USCIS is not a law enforcement agency so it's not allowed under some treaty, apparently.

If you have a US client and you live in Canada (i.e. you do not have a "fixed base" in the US) bear in mind you have to file a US tax return, 1040NR and claim the tax treaty exemption on Form 8840 (or 8833 depending on the situation). There is no tax to pay, it's just a reporting requirement. If the income is less than $3,400 you just have to file the 8840 or 8833.

If you start doing the work in the US and you have US clients it gets much more sticky on the tax end of it as they have to do withholding and you need to register as self-employed, etc.

First time you file if you are still living in Canada apply for an ITIN as well, that will help you in the future.

I guess your enrollment in Canadian college shows enough tie that you will return in short term, at least this summer.

Bring your prove of enrollment and transcript.

Yes, I don't think anyone will know if you are actually telecommunicating and actually working given the nature of your job.

Well, for long it is more complicated and explained detailly above

Yeah, showing that I'm a student (as well as showing bills etc.) generally gets them to let me through when there's doubt. And I have no criminal record so there's no problems there.

I've read conflicting information about whether or not I do in fact need to file a tax return with the IRS if I'm not a resident alien (which I'm not). I'll have to look into that.

Thanks folks.

If all your clients are in Canada and your business is in Canada you don't have to file a US return. If your income from US sources is less than $3,400 and you are self-employed in Canada you also don't have to file a return, however you still have to file a tax treaty claim.

Don't bother talking to Canadian accoutants about it, most haven't got a clue, phone up the IRS non-resident centre in Philadelphia. Most of their agents don't have a clue either but eventually you should get hold of someone.