Aboout one year ago, I moved from Toronto to Chicago for work. These two cities are extremely similar, in climate, geography, size, and culture. However, due to a quirk of politics, they happen to have an international border between them despite being just a couple hours by plane or a single day's drive away. This meant that when I moved I was not just changing my city of residence. Suddenly, I had become an expatriate.

Of course, a Canadian working in the US is far less culturally jarring than most other expatriate situations. Regardless, changing countries always involves switching to an entirely new legal, civil, and bureaucratic infrastructure, and this can sometimes run into problems. You may even encounter the most dreaded beast of all: immigration problems.

As usual, this post is inspired by other stories I've read. 18 Years A Transient, for example, chronicles an Indian engineer's long and arduous path towards gaining permanent residency in the USA. Before even getting started I'll say that the experience he went through, and that tens of thousands of others of immigrants go through each year, is far far worse than anything that happened to me. If you want a showcase of some of the worst contradictions and consequences of what it's like to be a foreigner working in America, you should really check that out.

This, on the other hand, isn't intended to be some great expose on the flaws of the USA's immigration system. Unlike the story I linked above, the roadblocks I faced were not intentionally set by the United States government. Rather than being a product of messy immigration laws and political infighting, my problems were simply a mix of technological issues, bureaucratic delay, and largely were directly caused or exacerbated by myself. I look back on it all mostly with a sense of faint amusement rather than any real frustration at the institutions that were involved.

<!-- Really, I think this story says more about me than it does about America's laws or bureaucracy. -->

To explain what actually happened, we need to go all the way back to 2021

December 2021 - Job Offer

In December of 2021, I got the job that would lead to me moving to Chicago. And, that's about all of the relevant parts from this month. Ok, maybe we didn't need to go back this far...

April 2022 - First Visit

Here we go. Because I didn't graduate until June 22, I didn't start working for a while. The first time I actually visited the US for anything related to the job was in April of 2022, where all of the new hires visited for a weekend to introduce ourselves and get familiar with the company.

Of course, I've visited the US many times before. As a Canadian it's very easy; at the border you tell them you're visiting for leisure and they let you in without even stamping your passport. Technically they only let you in for six months at a time, but there are stories of Canadians staying for much longer. There are few consequences, and really it's a sign of how closely these two countries cooperate and how intertwined the societies are.

At the border I told them I'm just there for a weekend and they let me right away. In fact it was even easier than that. I happen to be enrolled in the Global Entry program which means a machine scans my face and assigns me the correct visa (in this case B2, which is the standard temporary visa for Canadians) automatically. I appreciated the convenience in the moment but this seemingly innocuous technology will return later in the story. I thought nothing of it, bypassing the entire line at the border, but don't make the same mistake I did.

Anyway the rest of the trip went by without a hitch, and I returned home with nary a concern on my mind.

July 2022 - The First Real Entrance

Now is a good moment to explain some of the relevant laws regarding working in other countries. In the US, aliens (meaning non-citizens) are not allowed to work by default. To do so, you need to obtain a visa specifically letting you reside and work in the country. Oftentimes this is done to filter out the lowest quality workers - they want to keep the poor labourers and minimum wage employees out while letting the wealthy lawyers and engineers in. Whether or not you believe this is efficient or moral, it's simply how nations work and just about every single one has a system like this in place.

There are a few ways for people to get long term work visas. The very rich or the very famous have it pretty easy, with very little wait. The most common way if you have a university degree is to apply for something called an H1-B visa which is pretty universally despised by all who have the misfortune to need it. There is a literal lottery to get this visa, which wasn't so bad a few decades go when the odds were decent. But now there's only about a 20% chance of getting it with only 3 tries before they must leave the country. Seriously, look at this excerpt from the article at the top:

Each year, across all of America, there’s a maximum of 85,000 new H1B visas that will be awarded – 20,000 of which are reserved for those with advanced degrees from an American university. If there are more qualified applicants than this limit, a lottery is used to randomly decide who gets the visa and who doesn’t – incentivizing companies to stuff the lottery with as many applicants as possible, in order to maximize the company’s odds. At one of my internships, we used to host “The Deported” parties every year in order to bid farewell to colleagues who got unlucky in the lottery and had to leave the country.

This is the single biggest source of legal anxiety that immigrant workers face. Imagine losing your job, and on top of the usual financial concerns, you now also have a 60-day deadline to find a new job. And if you’ve spent the first 45 days interviewing only to wind up with rejection notices, you now have just 15 days to withdraw your kids from school, pack up all your belongings, buy plane tickets and hotel accommodations, and move your family to a new country

There are a lot more juicy details to this system, including the fact that H1-B is a temporary work visa. Even after getting it there's a long long path to permanent residency and getting a green card. That's all down a huge tangent though, since the visa I was getting was not an H1-B.

Luckily for me, the USA has an agreement with Canada and Mexico under NAFTA (the North American Free Trade Agreement) to allow certain professionals to be employed in America. This happens to be bilateral, so Americans and Mexicans can use the same method to come and work in Canada. It's all designed to be very straightforward and simple, unlike the arduous process involving the H1-B. You don't even need to fill out any special forms - you just show up at the border with the right documentation and they almost always let you in. Key word being almost.

Before we get to the actual scene of my border crossing, there's something you have to understand about me. I'm very optimistic, to a fault even. I really don't believe that things will go wrong, and they generally haven't. I do concede that there are some situations where perhaps I should approach with a little bit more care. Despite everything that happened however, including the events of this day, I still firmly believe this is the best attitude to carry throughout life.

So about a month before I started work, I moved to the US to get settled in and prepare my new apartment. To do that, I traveled from Toronto to Chicago the exact same way I did last time, and I was anticipating a painless border experience once again. They would have waved me right through without any issues, except that I chose that moment to apply for a TN visa.

This was technically the correct procedure, except I didn't have any of the necessary paperwork or know any of the procedures to properly apply. In that moment part of me wondered if I should be more careful, having only skimmed the requirements and only knowing that you apply at a port of entry but not exactly how; in the end, though, I knew that nothing bad could really happen whereas something interesting could. I just cast my die into the wind, abandoned myself to fate, and trusted that no matter what my unshakable faith and optimism would carry me through.

They brought us into secondary inspection and the agent became quite exasperated that I was here with literally zero documentation for the TN visa apart from a few haphazard screenshots on my phone. She was quite terse, and this was a fairly stressful moment because all the while I was expected to pick up the keys to my new apartment, the IKEA people were calling to arrange delivery, and I was supposed to meet my parents later that day. I admit, for a moment I was slightly concerned about what might happen but that thankfully didn't last long.

Eventually, after consulting with a manager, the agent decided she could let me into the country on a regular visa as long as I pinkie promised not to start work before leaving the country and reentering with the correct documentation. I found this to be relatively gracious, after reading horror stories online about what the agents can do if they find you suspicious. However, my brother who was with me at the time found the whole experience to be quite harrowing, to a surprisingly deep degree. Clearly we didn't share the same faith that nothing really could have gone wrong.

Anyway the rest of that trip went smoothly if a little chaotically. I had no other issues dealing with any levels of government, and eventually my workplace mailed me the documents I needed for the TN visa. Armed with everything I needed, I headed back to Canada to get the visa for real.

August 2022 -- Getting the Visa Day 1

Like I said above, getting a TN visa is supposed to be straightforward for Canadians. You show up, ask nicely, maybe share some documents, and then you're home free. The idea is that you can do this whole thing at the airport quick enough that you'll make your flight. The Toronto Pearson Airport does the processing for visas before you get to the gate, to make it extra convenient. Unfortunately it didn't go as smoothly as I planned.

I was planning to get my TN visa and fly back to the US after a brief stay in Canada, just long enough to get some stuff I'd left and say goodbye. To that end, I was carrying two huge boxes of stuff, one of which had my computer parts and so I needed to be careful. As per my plan I arrived at the airport extremely early, and painstakingly lugged around these boxes to the check in desk and then to the oversized luggage area. After finally relieving myself of this burden, I went through US customs and asked for a TN visa.

The tired looking agent barely glanced in my direction before pointing me to the dreaded Secondary Inspection. At this point I was still feeling fairly upbeat, and with over two hours to my flight it seemed like I'd be fine. However when I saw the amount of people waiting in here with me I started to get nervous. I didn't know it at the time, but a popular Caribbean festival called Caribana had just finished, which meant hundreds of festival goers were trying to fly back to the US.

There were at least a few other TN applicants sharing my plight. At one point one of the agents even announced that if any of us wanted to just enter the US and skip getting their special visa he'd just let us through, because there would be significant delay. Of course I didn't accept that option since I still had a few days until I started work and had time to get authorized, but it didn't bode well.

Still though, I was in a pleasant mood. I find places like airports to be eminently fascinating, and here I had a chance to watch people at their best and (more often) their worst moments. There were some colossal freakouts and some fascinating stories to be heard, and I was spending my time people watching. Eventually the time of my flight came and went but still I persevered; I figured I might as make sure to get the visa and they'd probably put me on another flight tomorrow.

Finally, my moment of truth arrived. I was called up by an agent to look at my application package. He asked me a few questions about what the company did and my role in it, but to my horror he denied my application. I learned that many other Canadian trainees, who drove instead of flew, used the exact same application package to make it through in just a few minutes. Here I was after waiting for 3 or 4 hours only to be denied.

I think this illustrates another essential part of any bureaucratic process that just can't be controlled - an element of luck. Somethings things just go your way, and sometimes they don't through no fault of your own. Maybe the agent was having a bad day or maybe there really was a flaw in the application. The TN visa is only permitted for a specific list of designated, NAFTA professions and I don't think he understood how my new role related to that list.

Either way, I was cast out of the airport and sent to collect my bags. To make things even worse, I had to wait another hour for my two huge boxes to be sent back outside and for someone to come pick me up. The one saving grace in all of this was that my new workplace was extremely sympathetic throughout this entire process. They assured me that I did nothing wrong and arranged to send me new documents overnight so I could try again tomorrow. After doing some frantic research for new flights and planning out my next day, I finally had some well deserved sleep.

August 2022 (still) -- Getting the Visa Day 2

The plan for today was essentially identical to yesterday. I got to the airport early, lugged my two huge boxes around until the oversize luggage area was open to check them in, shambled through US security with practiced ease, and declared that I was applying for a TN visa. And then, the waiting began.

I was started to get a little bit low on reading material, having exhausted most of it during my 4 hour wait yesterday. Plus I didn't want to use headphones in case there was some juicy drama happening that I would miss out on. I was still feeling confident overall, if a little less so, and there was still plenty of people watching for me to amuse myself with. As the wait stretched on, however, it seemed like it would be no better than yesterday. If true, that would mean once again missing my flight. I wouldn't even mind that too much as long as I got the visa.

Amusingly, some of the agents started to recognize me. One of them who seemed a little bit younger and a little bit friendlier than the others was my favorite. I gave him a nod as I walked in; I thought it was funny to be seeing him again for the second day in a row. He even called me up after I arrived to ask about my situation, I think mostly out of curiosity, and I gave him a quick explanation.

So, the hours passed. I got lots of reading done and overheard some more fun stories, like the lady who had a breakfast orange in her purse and so had to miss her flight (no fresh fruit is allowed to cross the border). Or the family going to Disney World for the first time. Once again the time of my flight quickly passed, but I remained unfazed. I couldn't wait to see how the actual visa application would go. And finally, I was called up.

To my relief, the agent was the friendlier one this time. I told him the same things that I said yesterday, and he sent me back to my seat while he considered. As I said before, I rarely get nervous even in the most stressful situation; this however, had me shaking. In retrospect I think I was being a little bit dramatic, but after waiting for over 10 hours in total I was very invested in the outcome.

As I said, I think luck is a huge factor in stuff like this, and is why I got denied the day before. The documents I had today were, frankly speaking, 99% similar to what I then. I didn't say anything new either in the interview. The entire difference, in my mind, comes from the fact that I got the young friendly border agent this time, as opposed to yesterday's stricter one. Even luckier, the one from yesterday wasn't in today.

The new agent asked a few questions to figure out why the last guy denied me. It seemed like he liked my application overall (since, of course, everybody else got the TN visa just fine) but also didn't want to completely undermine the other agent's decision. Waiting there in the seat, ears perked to hear any scrap of what they're saying, hoping that I wouldn't have to repeat this again tomorrow; it was a rough few minutes. Eventually I heard the agent mutter the fateful words: "sigh, I'm just gonna give it to him".

My guess is he was trying to identify whatever flaws the agent from yesterday found, but eventually gave up on that and decided to just go with his gut. Whatever the reason was, I felt vindicated in my optimism and despite all that I went through I mostly returned to believing that everything will probably turn out fine in the end.

Now, I had one last hurdle. Since I missed my flight again I had to book another one for tomorrow so I could fly to the US with my shiny new TN visa. My boxes and I went back home and I once again quickly fell asleep, knowing tomorrow would be the day I finally reached Chicago.

Some Fun Info about the TN

Now might be a good time to discuss how the TN visa actually works, as it's central to this story. I've actually been incorrect this whole time every time I mentioned the TN visa; such a visa does exist but it's not what I was getting.

You see, immigration can be a strange and confusing process. The USA and Canada have a treaty to allow for visa-free travel between the two countries. That means that for the most part, Canadians entering the country don't require permission to enter. No visa means you can just drive up to the border and drive through.

However, the USA can't just let us Canucks run around willy nilly south of the border. Even if entry is widely permitted, they still have rules regarding things like employment and length of stay.

To solve this, the USA keep track of the class of admission when a Canadian crosses the border on a entry document called the I-94. Whenever I wrote TN Visa, I more accurately should have said TN classification, or TN status. This is determined at the time of entry by the individual agent, and is meant to be quicker and easier than a full visa.

If you've ever tried to get a US Visa, you'll know that it's a whole thing. You need to mail in your passport, visit a consulate, get fingerprinted. It goes through a whole department in the US government that needs to approve you. The actual visa even takes up a full page in the passport with color and everything - it's a whole deal.

TN status on the other hand is a whole lot simpler. You show up at the border, present a few documents, and the idea is the agent lets you on your way within maybe half an hour (although the company can apply on your behalf if they'd like). As you saw from my two days in the airport it's not always this straightforward, but the idea is there. Most other Canadians I knew had much nicer experiences crossing at land borders rather than relying on the overloaded Toronto Pearson Airport.

Also, unlike most other work visas, you don't require sponsorship. The company typically writes a letter requesting entry, but if you have an offer and the right documents, you could get the visa entirely by yourself without involving your employers at all. There's certainly a lot less restrictions in the process compared to the onerous process involved with an H1-B, for example (which if you're interested in learning more about, you really should read the article I shared above).

There are a few quirks and downsides though. Firstly, whether or not you get the TN classification is up to the discretion of the individial agent at the border crossing, which means that a few unlucky souls may have an experience like mine or even be permanently rejected.

A more important aspect however, is that the TN is a nonimmigrant classification. You're meant to use it to work in the US, not to move your entire life here and become a US citizen. Unlike other visas, there's no path to permanent residency or a green card, even if it can be theoretically renewed indefinitely. Every three years at renewal, the agent might deny you if they feel you have intentions to immigrate and settle down here.

Plus, remember that this is a temporary classification and not a visa. Every time you leave and reenter the US, like on vacation, technically an agent has to manually put in your TN status which they can sometimes forget or choose not to give you. Every time I've entered and explained I previously had TN they've just given me one with the same expiration date without questions, but technically they could interview or deny me right there. It's advised to keep all your TN documents with you when reentering, which I never do of course because, just in case you have issues.

As you can see there are a lot of rules and details involving this visa, but it's still better than the H1-B which involves signing up for a literal lottery.

August 2022 -- Getting the Visa Day 3

So, I showed up to the airport for the third day in a row bright eyed and bushy tailed, ready to move to my new home. Unfortunately, the airline was not very willing to rebook my flight and the check in counter couldn't do anything. I stayed on the phone with the airline for almost an hour before I got too nervous and purchased a new ticket (for the flight I was meant to be rebooked on) myself.

Funnily enough, after getting through security, they did eventually rebook me so I ended up with two tickets for the same flight. I think the staff at the gate were kind of amused by this.

First though, I had to get through immigration. I had already been approved for TN status yesterday, but like I said you technically have to be reapproved every time you enter the country. That meant that theoretically, there was a small chance I would be instructed to head to secondary inspection and wait there again. As funny as it would have been to meet those same agents for the third day in a row, I really didn't want to risk ending up there again.

So, you might say I checked out and I used my Global Entry card to skip the line and go straight through. Keen eyed readers may notice something at this point - does the Global Entry machine know that I'm entering with a TN status or will it assign me a B2 status like it did when I arrived in April? Well funnily enough, I wasn't thinking about this at all! At this point in time I had no idea how the system worked, and I just wanted to get to the US.

Spoiler alert: it gave me a B2.

I didn't realize this until right before I boarded my flight which completely shattered my happy mood. I spent the entire 2 hours anxious about the consequences of what would happen. Would I have to fly back and reenter? Would I even be allowed to work?

Luckily it didn't turn out to be a problem at all. I emailed my workplace for advice and since I had the stamp and everything from before, the government corrected me in their system; it all turned out to be a complete nonissue.

The relief I got from bringing my two massive boxes back to my apartment and sleeping in my own bed was huge. I literally had a huge weight off my shoulders. The next few days were full of small tasks related to starting a new job, but everything was smooth sailing for the next few weeks.

October 2022

I'd been working for a couple months at this point. I finished training, started my new role, and was working hard. There was only one issue - for the past two months I hadn't been paid.

The reason was because I hadn't received a social security number yet. I applied when I first started just like everyone else, but after patiently waiting for months there was still no word from the Social Security Administration. The problem was that the USCIS was taking ages to verify my immigration status.

I had a few unsubstantiated theories about why this might be. Maybe it had to do with the fact that I entered with a B2 and to have to corrected to TN, or something about my name. Or, as I complacently believed for months, there wasn't really a problem and I waited patiently all would be fine. I didn't even ask my HR department for help until I was one and a half months in, to give you an idea of my sense of urgency.

It was funny. I'd spent years living as a poor student and so sliding back into my frugal ways felt extremely natural. It was what I was used to, and so it felt comfortable to not worry about being paid and just try not to spend too much. Eventually though, HR figured out a solution to pay me despite not having a social security number, and I got everything I was owed. For a short while though, it was a slighly worrying time.

November 2022

At this point, I'd visited Toronto about 2 or 3 times. And, I had issues with not correctly entering with the TN status 2 or 3 times. I eventually realized that the source of these issues were using my Nexus card, since Global Entry automatically assigned me B2 status when I entered. This was something I'd need to fix with the Global Entry program to have them recognize my TN.

I distinctly remember one time when I was testing this. I used the Global Entry machine, but specifically asked the agent make sure it says TN status on my I-94 which she happily agreed to. I checked later and surprise surprise, it said B2. Eventually I learned how the TN is not a visa but just an entry status that resets every time you enter. Clearly I wouldn't be able use my Nexus card to enter the US anymore, but other than that all was fine.

Well, everything except for my social security number. Luckily I didn't technically need it to work or enter the country, but without it I couldn't get credit cards, a driver's license, or open a 401k to invest for retirement. It wasn't a huge inconvenience, but annoying enough that I wanted to figure it out.

Unfortunately getting information on this problem was not easy. All I knew was that it was stuck forever with USCIS, the branch responsible for verifying my immigration status. The Social Security Administration didn't know anything beyond that, and the USCIS was impossible to get in touch with. The phone line would literally hang up on you after spelling out the URL for their website, and said website only had a distinctly useless chatbot called Emma.

I theorized that there was probably some secret phrase you could say that would connect you to a human but I couldn't figure it out. All I could do was wait.

Feburary 2023

It had been 6 months since I started work, and still no work on my social security number. It was close to tax season, which I couldn't do without it, so HR was getting a little nervous. At this point I'd reapplied for the social security number twice, and HR said they asked their lawyers to look into it but personally I don't really know if they ever did.

I did get a vital piece of information though. I'd called social security enough that they knew who I was and one of the agents there was very helpful throughout the whole process. You might say I had my own inside man.

She informed me that it turns out there was someone with the exact same name as date of birth as me which was confusing the system. I'd love to meet this person, but at the moment it seems like a quirk of fate had led to this causing a whole bunch of problems. Unfortunately we still didn't know how to fix this since the problem was with the USCIS system who I couldn't get in touch with.

Recall that Canadians don't need a visa to enter the USA. That means I can't identify myself with a visa number (which I would have if I ever got a real visa) or an A number (which I would have if I applied for a green card). All I had was my passport number and I-94 (which changes every entry). I suspect the USCIS systems aren't very smooth in these situations, since they normally deal with immigrants who have visas.

Regardless though, I want to stress that I really wasn't too concerned. Everything I wasn't able to get, like a credit card or driver's license, I had Canadian versions of. Due to the friendly relations between Canada and the US everything worked here like it did before, and so my quality of life was hardly impacted by all this delay. In fact, I think I sometimes got more amusement from telling my friends about the problem than I was actually inconvenienced by all this.

Plus, around this time I finally was able to update my Nexus card to use my TN visa. Now I could breeze through immigration and reliably get TN status on arrival without involving a human in the process. It made it much easier to travel and resolved one of the last big annoying issues I had.

April 2023

I'd been going back and forth with social security for weeks, without much progress. My contact suggested I try to meet with USCIS directly, or even try to ask the DHS guys next time I enter the country. We theorized about what the cause could be and potential database mismatches, but nothing too fruitful.

Around this time, my relentless calling of the DHS led me to some insights. It turns out there is a secret codeword you can say on the phone to USCIS, which will then connect you to a human. You didn't hear it from me, but the secret word is infopass.

Using this information I was able to book a real appointment with real humans from USCIS and ask them about my problem. At the appointment it was kind of funny; they were very sympathetic but they couldn't directly go into the database and fix anything. All they could do was suggest formatting my name in a slightly different way so that it didn't conflict.

It wasn't the most watertight idea but I was pretty optimistic. This stage felt like reaching the final level in a video game, down to having to get past each individual miniboss (the phone agents) to get to the final battle at the end. It would be such a perfect climax to the story, surely it had to work! I informed my friend at social security about my findings and we submitted an application again, for what would hopefully be the last time.

June 2023

It happened. In the online portal the USCIS said my application was reviewed, and I confirmed with social security that it wasn't confused with the other person again. At last, it seemed like I was about to recieve my card!

It took a while to arrive in the mail, almost long enough to make me doubt whether I'd really get it. As soon as I did, I got a credit card and a driver's license and a 401k. Honestly I had been working on this for so long, while I was happy I could finally move on with my life, I was almost sad to say goodbye to this era. It was exciting to always be checking on my application status, to be theorizing with HR and legal about what could be going on. To look forward to finally getting it so that everything could move forward.

Now I have it, and things haven't really changed that much. It doesn't really compare to the thrill of the hunt or the delicious anticipation of waiting. It was certainly a unique and interesting experience to have - what are the chances someone would have the same name and birthday as me! If only there were some way to track him down.

Moral of the Story

Hold on, moral of the story? Not every story needs to have a moral. I had fun, bureaucracy is slow, that's it.

I do want to say a few things though. It's interesting that at every stage of the process, I received nothing but sympathy and kindness from the people I interacted with. Even the worst border agents were really just a little curt but never really rude. It's funny that at times it felt like it was all of us vs. some inhuman technology that we can't do anything about.

Another thing to note is that while it might seem like this exposes flaws in the US immigration process, every delay was really on me. I wouldn't have had a scare at the border if I actually knew the rules for the TN status beforehand. I could have been paid sooner if I asked HR about it right away. I could have figured out the social security problem if I was more proactive about calling them and insisting on help.

For the most part, I really just tended to sit back and assume it'll all work out somehow. And while it mostly did, it could have worked out faster if I wanted it to. However, I don't know if I'd change anything. I figured everything out eventually and I was happy to take it slow and be stress free along the way.

It's funny that for an immigration system that has so many intentional hurdles and roadblocks for most types of immigrants (such as those chaps unlucky enough to need an H1-B), I faced such unintentional difficulty doing something that was supposed to be easy. Pretty much everyone else from Canada got the TN visa without an issue and had their SSN within a couple of weeks. If anyone had to face this stuff though, I'm glad it was me. It makes for a great story, a good blog post, and some fun insights into whole immigration system.

I'm glad that I can finally leave these issues behind focus on the next big adventure. At least, that's until I have to renew my TN status. They only give it out for 3 years at a time, so in August 2025 maybe I'll have to repeat the process. Until then, I'm happy to put this all behind me and appreciate finally appreciate resinding fully legally in the USA.