Frequent trips to Canada

[Raizen21]

I'm a US citizen from NY with a Canadian PR girlfriend who lives in Halifax, NS. We've been together (LDR) for 3+ years and have known each other for a lot longer than that. I'm a software developer who can work remotely. I work full time (W2) for an NJ based agency though some of our employees including me are part of a team that contracts for a company that has offices in both US and Canada but that does their own hiring. The NJ based employer still pays the salary of everyone on our team. I can also potentially ask to be switched out to a team that doesn't work for that company.

I visited my girlfriend last Nov. 2021 for ~15 days and again between mid Feb. to mid Mar. of this year for 32 days. For my first visit, I was only asked my purpose of visit/length of stay by CBSA (through Montreal) iirc. For the 2nd visit (through Toronto) I was asked more questions such as several about our relationship, what I do, when's the last time we were together (to which I answered Nov 2021) and why I was staying 32 days but I don't think that one counted as being pulled into secondary. We are planning to visit Toronto and Montreal from June 18 to 27 (thinking I fly back to NY from whichever city we visit last on the 27th). I would like to start my visit between mid-late May though if I could, but if I do that how high is the risk of being denied entry? I still live with my family so I don't exactly have a lease. I'd only be able to show return ticket, travel insurance, sufficient funds. If I start my visit in mid-late May then I'd be working til June 18, I won't volunteer this information but if asked will the work situation above cause any issue?

Is there any path for me to be able to visit her frequently without CBSA trouble while maintaining my employment? We've talked about marriage but it's not something we see happening until the 2nd half of next year.

I'm not sure I'd like to max out the 6 months in one visit as that would have tax implications as well so I tried spacing them out though I realize some agents might consider them too frequent. I'd like to avoid getting into trouble and jeopardizing our future for when we eventually apply for spousal sponsorship especially after reading that US citizens tend to have quicker/easier (relatively) PR applications.

Thanks all!

 

[Copingwithlife]

Visit her frequently without trouble ? You gotta remember it’s not a right for you to visit , it’s a privilege. If they’ve asked you more questions, you’ve popped up on the radar . You shouldn’t give the appearance of living here , regardless whether you can work remotely. And as you mentioned since you have Canadian offices, that’s on thin ice .Why doesn’t she visit you ?

 

[lossada]

I'm a US citizen from NY with a Canadian PR girlfriend who lives in Halifax, NS. We've been together (LDR) for 3+ years and have known each other for a lot longer than that. I'm a software developer who can work remotely. I work full time (W2) for an NJ based agency though some of our employees including me are part of a team that contracts for a company that has offices in both US and Canada but that does their own hiring. The NJ based employer still pays the salary of everyone on our team. I can also potentially ask to be switched out to a team that doesn't work for that company.

I visited my girlfriend last Nov. 2021 for ~15 days and again between mid Feb. to mid Mar. of this year for 32 days. For my first visit, I was only asked my purpose of visit/length of stay by CBSA (through Montreal) iirc. For the 2nd visit (through Toronto) I was asked more questions such as several about our relationship, what I do, when's the last time we were together (to which I answered Nov 2021) and why I was staying 32 days but I don't think that one counted as being pulled into secondary. We are planning to visit Toronto and Montreal from June 18 to 27 (thinking I fly back to NY from whichever city we visit last on the 27th). I would like to start my visit between mid-late May though if I could, but if I do that how high is the risk of being denied entry? I still live with my family so I don't exactly have a lease. I'd only be able to show return ticket, travel insurance, sufficient funds. If I start my visit in mid-late May then I'd be working til June 18, I won't volunteer this information but if asked will the work situation above cause any issue?

Is there any path for me to be able to visit her frequently without CBSA trouble while maintaining my employment? We've talked about marriage but it's not something we see happening until the 2nd half of next year.

I'm not sure I'd like to max out the 6 months in one visit as that would have tax implications as well so I tried spacing them out though I realize some agents might consider them too frequent. I'd like to avoid getting into trouble and jeopardizing our future for when we eventually apply for spousal sponsorship especially after reading that US citizens tend to have quicker/easier (relatively) PR applications.

Thanks all!

Canada border officers are a lotto, we never know what's going to happen, even for us.
Just be original,,,
She should apply for Canadian citizenship, as soon she can, just in case.

CANADA
you can stay up to 6 month and extend
taxes if you live less than 180 days,,, no tax files
if you proof you live one year together she can sponsor you
You could married in Canada,,, sponsor might be easier
you should go to a paralegal o legal advisor
You can apply for a TN VISA

USA
you could apply a K visa for her
then married her in the USA

 

[Cassiano]

I'm a US citizen from NY with a Canadian PR girlfriend who lives in Halifax, NS. We've been together (LDR) for 3+ years and have known each other for a lot longer than that. I'm a software developer who can work remotely. I work full time (W2) for an NJ based agency though some of our employees including me are part of a team that contracts for a company that has offices in both US and Canada but that does their own hiring. The NJ based employer still pays the salary of everyone on our team. I can also potentially ask to be switched out to a team that doesn't work for that company.

I visited my girlfriend last Nov. 2021 for ~15 days and again between mid Feb. to mid Mar. of this year for 32 days. For my first visit, I was only asked my purpose of visit/length of stay by CBSA (through Montreal) iirc. For the 2nd visit (through Toronto) I was asked more questions such as several about our relationship, what I do, when's the last time we were together (to which I answered Nov 2021) and why I was staying 32 days but I don't think that one counted as being pulled into secondary. We are planning to visit Toronto and Montreal from June 18 to 27 (thinking I fly back to NY from whichever city we visit last on the 27th). I would like to start my visit between mid-late May though if I could, but if I do that how high is the risk of being denied entry? I still live with my family so I don't exactly have a lease. I'd only be able to show return ticket, travel insurance, sufficient funds. If I start my visit in mid-late May then I'd be working til June 18, I won't volunteer this information but if asked will the work situation above cause any issue?

Is there any path for me to be able to visit her frequently without CBSA trouble while maintaining my employment? We've talked about marriage but it's not something we see happening until the 2nd half of next year.

I'm not sure I'd like to max out the 6 months in one visit as that would have tax implications as well so I tried spacing them out though I realize some agents might consider them too frequent. I'd like to avoid getting into trouble and jeopardizing our future for when we eventually apply for spousal sponsorship especially after reading that US citizens tend to have quicker/easier (relatively) PR applications.

Thanks all!

don't think to much, border officers are unpredictable, just be prepare and spontaneous
go, and stay with her les than 180 days to avoid taxes in Canada if you want / it's up to you
pay taxes would help you in the future in Canada.

 

[Raizen21]

Visit her frequently without trouble ? You gotta remember it’s not a right for you to visit , it’s a privilege. If they’ve asked you more questions, you’ve popped up on the radar . You shouldn’t give the appearance of living here , regardless whether you can work remotely. And as you mentioned since you have Canadian offices, that’s on thin ice .Why doesn’t she visit you ?

Right, I'm aware I'd only be a visitor and hence I'm just looking for balancing the time spent apart vs together while still honoring Canada's laws.

Technically, our company doesn't have any offices in Canada. Also, she recently just became a Candian PR but still a Filipino citizen.

 

[Raizen21]

Canada border officers are a lotto, we never know what's going to happen, even for us.
Just be original,,,
She should apply for Canadian citizenship, as soon she can, just in case.

CANADA
you can stay up to 6 month and extend
taxes if you live less than 180 days,,, no tax files
if you proof you live one year together she can sponsor you
You could married in Canada,,, sponsor might be easier
you should go to a paralegal o legal advisor
You can apply for a TN VISA

USA
you could apply a K visa for her
then married her in the USA

Thanks for these.

 

[canuck78]

Right, I'm aware I'd only be a visitor and hence I'm just looking for balancing the time spent apart vs together while still honoring Canada's laws.

Technically, our company doesn't have any offices in Canada. Also, she recently just became a Candian PR but still a Filipino citizen.

The fact that your employer has links to Canada is the big issue. You can’t work remotely from Canada if your employer has offices or customers/clients in Canada. Given that you were already questioned creates increased chances of being questioned again. You have already spent a month in Canada and are looking to spend another month which is quite a long time. The fact that you don’t have your own home means that you are at a higher risk of remaining in Canada.

 

[Raizen21]

The fact that your employer has links to Canada is the big issue. You can’t work remotely from Canada if your employer has offices or customers/clients in Canada. Given that you were already questioned creates increased chances of being questioned again. You have already spent a month in Canada and are looking to spend another month which is quite a long time. The fact that you don’t have your own home means that you are at a higher risk of remaining in Canada.

I guess the fact that the company has a client that has offices in Canada is the issue here regardless of whether or not I'm in a team that works for that client?

Also, considering the last time I was there was mid-Mar, if I wanted to stay a month when would be a reasonable time to go back again? If, on the other hand, I just stay two weeks how often can I realistically expect to go?

And the increased chances of being questioned applies even if I technically wasn't pulled into secondary? The fact that every entry is assessed differently doesn't apply here or it's the frequency that would warrant more scrutiny?

Is there any visa/program I can apply for that would allow me to live/work in Canada and stay at my current employer before I eventually get married to my gf?

Thanks for all the input!

 

[lossada]

I guess the fact that the company has a client that has offices in Canada is the issue here regardless of whether or not I'm in a team that works for that client?

Also, considering the last time I was there was mid-Mar, if I wanted to stay a month when would be a reasonable time to go back again? If, on the other hand, I just stay two weeks how often can I realistically expect to go?

And the increased chances of being questioned applies even if I technically wasn't pulled into secondary? The fact that every entry is assessed differently doesn't apply here or it's the frequency that would warrant more scrutiny?

Is there any visa/program I can apply for that would allow me to live/work in Canada and stay at my current employer before I eventually get married to my gf?

Thanks for all the input!

TN VISA
https://www.canada.ca/en/immigration-refugees-citizenship/corporate/publications-manuals/operational-bulletins-manuals/temporary-residents/foreign-workers/international-free-trade-agreements/north-american.html

Computer Systems Analyst

Baccalaureate or Licenciatura Degree; or Post-Secondary Diploma or Post-Secondary Certificate, and three years’ experience.

• “Post-Secondary Diploma” means a credential issued, on completion of two or more years of post-secondary education, by an accredited academic institution in Canada or the U.S.

 

[canuck78]

I guess the fact that the company has a client that has offices in Canada is the issue here regardless of whether or not I'm in a team that works for that client?

Also, considering the last time I was there was mid-Mar, if I wanted to stay a month when would be a reasonable time to go back again? If, on the other hand, I just stay two weeks how often can I realistically expect to go?

And the increased chances of being questioned applies even if I technically wasn't pulled into secondary? The fact that every entry is assessed differently doesn't apply here or it's the frequency that would warrant more scrutiny?

Is there any visa/program I can apply for that would allow me to live/work in Canada and stay at my current employer before I eventually get married to my gf?

Thanks for all the input!

Sorry thought you were pulled into secondary. Very hard to predict whether your next visit will be an issue. You seem to be visiting at pretty regular increments so you could be questioned. The fact that you are living with your parents means that you don’t have as many ties forcing you to return yo the US. Think you should enter Canada with the understanding that you technically shouldn’t be working remotely from Canada and that you could be questioned about how much time you are spending in Canada. It does seem like you are going on vacation for part of the time which is less of an issue. You’ll need to get a feel for how CBSA views your entry and react accordingly. You may have zero issue. There aren’t any programs that would allow you to live in Canada and keep working for your employer.

 

[Raizen21]

TN VISA
https://www.canada.ca/en/immigration-refugees-citizenship/corporate/publications-manuals/operational-bulletins-manuals/temporary-residents/foreign-workers/international-free-trade-agreements/north-american.html

Computer Systems Analyst

Baccalaureate or Licenciatura Degree; or Post-Secondary Diploma or Post-Secondary Certificate, and three years’ experience.

• “Post-Secondary Diploma” means a credential issued, on completion of two or more years of post-secondary education, by an accredited academic institution in Canada or the U.S.

Thanks for the link! I will look into this.

 

[Copingwithlife]

Sorry thought you were pulled into secondary. Very hard to predict whether your next visit will be an issue. You seem to be visiting at pretty regular increments so you could be questioned. The fact that you are living with your parents means that you don’t have as many ties forcing you to return yo the US. Think you should enter Canada with the understanding that you technically shouldn’t be working remotely from Canada and that you could be questioned about how much time you are spending in Canada. It does seem like you are going on vacation for part of the time which is less of an issue. You’ll need to get a feel for how CBSA views your entry and react accordingly. You may have zero issue. There aren’t any programs that would allow you to live in Canada and keep working for your employer.

Even though they weren’t pulled into secondary, the information the officer saw gave them reasons enough to ask more questions the second time around . His entry date, his exit date.
And as mentioned there’s no way not to be asked questions . You’re assessed each time upon entry , and your travel history will be looked at