What Canadians Should Know About US Entry Waivers and Working South of the Border

Crossing into the United States isn't always as simple as showing your passport, especially if you have a criminal record or you're hoping to work south of the border. In this episode of FH&P Lawyers' Law Talk, Clay Williams speaks with Kevin Cheung, who is called to the bar in both New York and British Columbia, about US immigration, including entry waivers, criminal record concerns, and what's involved in crossing the border to work.

Kevin is currently offering a FREE 15-minute consultation for US immigration inquiries, bookable directly through Kevin Cheung's profile page (offer valid until September 30, 2026).

What Is a US Entry Waiver, and Why Do People Need One?

A US entry waiver is required if something makes you inadmissible to the United States, most commonly a criminal record or history. If that applies to you, you'll need to prepare an entry waiver before heading down, whether you're going for work or play.

Does Everyone With a Criminal Record Need a Waiver?

Not necessarily, but anyone with a criminal record should at least get a legal opinion on whether a waiver is required. Certain crimes don't rise to the level of requiring one, but it's always best to check in with a lawyer first.

What Kinds of Crimes Actually Require a Waiver?

Some petty crimes don't rise to that level. But crimes involving possession of a prohibited substance, crimes involving assault, or what are known as crimes of moral turpitude can require a waiver, and yes, fraud can rise to that level, too. There's a long list of crimes that ultimately dictate whether you need one.

Where Are You Turned Back If You're Denied Entry?

Right at the border, at your actual entry point. If you're flying into Hawaii, that means the Hawaii border, not somewhere further along your trip. You can pay for your flights, get all the way down there, and still be turned around.

What Do You Need to Prepare a Waiver Application?

You'll need your court file from the criminal case, a number of letters of support from people who know you and can speak to your rehabilitation, and a letter from yourself addressing your remorse, along with a set of required forms. It's a comprehensive package, and one common pitfall is submitting something too thin or missing key documents, which usually results in being turned back.

How Long Does the Waiver Process Take?

Right now, it's about six months, though it really varies. It takes a lot of pre-planning, since putting the package together, getting your police check, gathering your criminal record, and getting letters prepared properly, can take several months, especially if you're starting from zero.

Is a Waiver Good for Life, or Does It Expire?

It only lasts for a few years, around five, so it does need to be renewed at certain points.

Does the Severity of the Crime Affect Your Odds of Approval?

Generally, the more serious the crime, the higher the likelihood of being turned away. That's part of why it helps to have a lawyer involved in preparing the package, so you've got the best possible shot at convincing them to let you in.

Who Decides Whether a Waiver Is Approved?

The border makes that call, and it's entirely discretionary whether an application is accepted. That's another reason it's worth putting together as strong a package as possible.

If You Have a Waiver, Are You Guaranteed Entry?

Yes. Once you have your waiver, you're free to go. The discretion happens at the application stage, not when you actually show up at the border with your family for that trip to Disneyland.

How Do the Americans View a Canadian DUI, Since It's Often Not a Criminal Charge Here?

If there's no criminal record attached, it likely doesn't rise to the level of requiring an entry waiver.

What About Old Marijuana Possession Convictions?

Marijuana is legal in Canada now, but it wasn't always, and plenty of people were charged with possession and ended up with a criminal record. Even a conviction from decades ago, say 1975, still counts. It doesn't matter that it's legal today: if you've got that record, you'll need an entry waiver.

Does a Canadian Pardon Clear Your Record for US Purposes?

No. The border doesn't recognize Canadian pardons, so a pardon doesn't wipe your record clean as far as US entry is concerned.

Do You Need to Disclose Charges That Never Led to a Conviction?

Probably not. It really comes down to whether you have a conviction on record. There's no obligation to disclose if you've only been charged and not convicted.

Does It Matter If the Conviction Happened When You Were a Minor?

Yes, as long as there's a criminal conviction on file, it counts, even if you were under 18 at the time.

Should You Just Disclose Everything Up Front?

Yes. It's better to be upfront and disclose all criminal convictions when you're making these applications or crossing the border, since you don't want anything surfacing later that gets you turned away. And if you've been denied entry once, that can make it more complicated to get in the next time.

What's the Basic Setup for Crossing the Border to Work?

It typically involves someone with a professional background or skill set that's useful in the US, paired with a US employer who's interested in bringing that person down to work. That combination is what triggers the paperwork needed to work legally in the US.

What Kinds of Professions Come Up Most Often?

Nurses are a pretty common example, and so are people working in the tech sector.

What Does the Paperwork Involve?

Part of it is working with the employer to make sure the offer letter is sufficiently specific about what exactly they're hiring the person to do, along with the rest of the required documentation.

Does Your Long-Term Intention Change the Process?

Yes, quite a bit. If you're heading down to work but you eventually want to become a US citizen and get a green card, that moves you onto a different pathway than if you only intend to work there for a few years. It's important to have that conversation and be clear about your intentions at the time you apply.

How Is This Different From a Green Card?

A green card isn't just a work visa, it's a pathway toward citizenship. That's very different from the type of work entry being discussed here, which is only a visa.

What Happens If Your Intentions Change After You're Already Down There?

If you go down intending to work for a few years but don't disclose that you're eventually planning to become a citizen, that can create problems when it's time to renew your status. People's intentions do change over time, and if that happens, they need to move onto a different pathway to work toward citizenship.

What Does the Actual Application Process Look Like?

Your employer prepares an offer letter and package, and you prepare your own entry package, a fairly comprehensive stack of paperwork. You bring that package to the border, and officers there decide whether everything is in order.

Do You Have to Go Through a Consulate?

As Canadians, there's actually a benefit here: this can often be done right at the border. That said, it depends on the type of status you're applying for. Certain entry pathways do require going through a consulate or a specific port of entry.

How Long Does This Type of Work Visa Last, and What Happens When It Expires?

In a tech sector example, three years is typical. When it expires, you have to extend it, which means going through the whole process again.

What's a Common Misconception for Remote Workers?

A frequent misunderstanding involves people living in Canada and working remotely for a US company. If you're working remotely from somewhere like Kelowna or the Okanagan, there really shouldn't be any US immigration issues to worry about. The problem comes up when you actually enter the US for work purposes, like attending a meeting, a work function, or meeting a client down there. The moment you cross the border for work, you need the proper status. Telling a border officer "I'm just here to do a little bit of work" is often exactly the kind of comment that triggers questions about your paperwork, and without the right documentation, you can be denied entry.

What About Canadians Who Own a Vacation Property in the US and Work Remotely From There Part of the Year?

If you're still working for your Canadian company while you're there, that's generally fine. But if you're employed by a US employer and doing work for them while physically in the US, you need to make sure you have the proper status.

Is There a Way to Get Some Initial Guidance Before Committing to a Lawyer?

Kevin is offering a free 15-minute consultation for US immigration inquiries, bookable directly through Kevin Cheung's profile page. It's a good way to get preliminary insight into the process, whether you're planning to travel to the US with a criminal record, planning to work there, planning to open a business, or dealing with any other US immigration matter. This offer is valid until September 30, 2026.

Whether you're dealing with an old conviction, planning a family trip, or exploring a job offer south of the border, the paperwork and the process matter, and getting it wrong can mean being turned away at the border after you've already made the trip. If you have questions about a US entry waiver or cross-border work status, contact the team at FH&P Lawyers. We can walk you through what applies to your situation. You can also read more in FH&P's related post, A Canadian Pardon Is Not Enough to Enter the United States.

Disclaimer: This material is provided for informational purposes only and should not be construed as legal advice on any subject matter. Consult with a qualified lawyer for advice on specific legal issues.