With the world’s longest undefended border it’s not difficult to become an accidental illegal alien, especially between the Yukon and Alaska.

After all, the last time there was a serious passport control on the Chilkoot Trail was during the gold rush. And not so long ago, a person could float down the Yukon River from Dawson City and clear customs at the general store in Eagle, Alaska.

So, it’s no surprise that Fairbanks cyclist Jeff Oatley found himself in hot water one year ago when he started a February trek from home travelling south along the length of the Yukon Quest trail.

He recalled his experience at a rest stop this year when he repeated the journey, northbound.

“In 2016 I got to Dawson and handed over my passport to immigration. Well, the immigration agent was like ‘How did you get here?’ By bike, I said. It went badly from there. The officer in Dawson was fairly certain I was going to jail in Whitehorse to be shipped to Vancouver for deportation back to Alaska.”

Oatley recalls being held for several hours before Dawson contacted Vancouver.

“They seemed to be more used to this kind of thing and checked my credit cards and bank accounts to make sure I could get myself home if anything happened,” Oatley says.

Eventually, he received a 21-day visitor’s visa.

Oatley remembers the incident was on Dawson radio news. “People kidded me about it at the Eldo.”

In an off-the-record conversation with an immigration advisor who wishes to remain unnamed, I learned such crossings happen more often than people think. Hunters cross borders back and forth as they stalk game, snowmobilers break trail, tourists experiencing the Yukon Quest or other aspects of the winter scene may not be paying attention – or know the rules.

What makes it difficult is that we don’t have an immigration office anymore. To sort it out, the person usually has to return to a formal port of entry – a customs office at a harbour, airport or highway checkpoint.

If the alien is someone from a NAFTA nation, or a European tourist, on an open work visa who’s helping with wilderness activities, such as cross-border races or expeditions, it’s more likely to be regarded as an oversight.

Not that it’s taken lightly. Even where the border stations are closed overnight, cameras monitor the lanes and the footage is reviewed every morning when the station reopens. As my source said, “They know if a moose has crossed the border.”

This year, biking from Skagway to Nome, Alaska, Oatley sent the Canadian Border Service Agency a detailed itinerary a month ahead of time since he would need to cross into and then out of Canada to cycle the most direct route – even though Skagway and Nome are both communities in Alaska. “They informed me of the checkpoint hours at the Fraser border,” on the Klondike Highway. Oatley made a point to wait for it to open. He was asked, “Ever had any trouble entering Canada?”

At this point you can believe the earlier infraction is permanently on record, so it’s advised to be as honest and transparent as possible. Each case depends on the person and how they present themselves. If the customs agent suspects a lie, things will only get worse.

In Oatley’s case, clearing customs wasn’t much of an issue as he was at a formal customs office. “The agent spent 15 minutes reading my file and said ‘Have a good trip.’”

On the way home he biked over the border somewhere along the 141st meridian. “There was more back-and-forth as I was entering at a place other than a checkpoint.”

But, the Americans also had his itinerary. The rout stitches together both the Yukon Quest and Iditarod Trails. “In the end, the agent [at Eagle] was there to check me in. He asked some questions about my bike, which he thought was pretty cool, and sent me on my way.”