Travel blogger Gary Leff can still conjure up the taste of the all-inclusive breakfast served at the Thai resort — not to mention the pinch of salt in the air outside his palatial beach-front suite.

A room worth $1,000 a night snagged for $33.

It's the kind of deal airlines call "a mistake", but Leff likes to think of it as "winning the lottery."

"It wasn't even so much that I'm thinking 'I paid $33,' — it was 'I'm here!" Leff, a man who's been called an 'Air Genius' for his mastery of the mysteries of frequent flying, told CBC News.

"It was wonderful. I realized I'm not ever going to pay for something like that, but I was certainly getting to enjoy it."

Dream trip at 'deep, deep discount'

Washington, D.C.-based Leff is part of an online army of deal-hunters who keep an eye out for mistakes like the one Air Canada made this week when the airline briefly sold an unknown number of business-class flight passes for a tenth of their $8,000 value.

It's a cat and mouse game between two not-so-innocent competitors: carriers constantly adjusting prices to lure consumers and bloggers trying to beat them at their own game.

Air Canada

Air Canada briefly sold business-class flight passes for a tenth of their $8,000 value. The airline says it won't honour the mistaken fare. (CBC)

Air Canada blamed a computer glitch for the error; the airline says it will refund passengers who haven't already used their passes to book flights. However, they're not planning to honour a mistake.

Leff, who publishes the blog View from the Wing, says that's par for the course in his world: You win some, you lose some.

"The way I view these things is I think it's great to take advantage of the opportunity when it's presented to have a trip of a lifetime at a deep, deep discount," he said. "And if it doesn't work out, then maybe it'll happen sometime again in the future."

Not if North American transportation regulators have anything to do with it.

The U.S. Department of Transportation used to force airlines to honour mistaken fares. But just this spring, they announced plans to revisit the policy.

The department cites "concern regarding how quickly mistaken fares are spread through postings on aviation and travel websites, forums, and blogs" in a notice about the changes.

Airline vs. frequent flyer

In essence, the issue raises a couple of ethical questions: Should an airline have to pay for an honest mistake? And does anybody feel bad about taking advantage of an airline?

Those were concerns addressed head-on by the Canadian Transportation Agency in a decision last year, rejecting a bid by 83 complainants to make Swiss Air honour a mistaken Yangon-Montreal fare.

First-class flights that would normally cost $10,000 to $15,000 US went for $113 to $150.

Swiss Air claimed a notice of the mistake made it on to a popular flying blog called Boarding Area. Suddenly, sales quadrupled. Most purchasers didn't even live in Myanmar.

"Swiss provided several excerpts from social media to illustrate that the complainants were: aware that the fares were a mistake; aware of the value of the mistaken fares; concerned that tickets may be cancelled; warned against raising suspicion and drawing attention to the mistake; and, encouraged to act quickly to take advantage of the mistake before it was discovered," the ruling says.

What is a 'legitimate fare'?

In their defence, the complainants argued validating the airline's arguments would reward them for making poor business decisions.

And they also claimed consumers are hard pressed to tell reality from a mistake when it comes to airline prices, especially in an era when computers tailor sales to individuals, and companies seem to constantly promise 'unbelievable deals' on flights.

Gary Leff

Gary Leff is a Washington, D.C.-based travel blogger. (View from the Wing)

"According to one complainant, there is no way for the consumer to know what a legitimate fare is anymore as carriers constantly change and manipulate fares to suit their business needs," the ruling says.

The agency sided with the airline — which means Air Canada is within its rights to refuse to honour this week's mistake.

However, that's not the end of the story.

Companies also have to deal with the inevitable public relations fallout of travellers — whether naive or cunning — going to the media with their tales of a dream trip turned sour.

Leff admits there's a certain thrill to beating the system, but he says there's also something in it for a savvy airline.

"I mean there's certainly the sense of finally beating the airlines because you always feel like they're beating you. But I don't view it that way. I think of it as winning the lottery. There's no malice in it. It's pure good fortune," he said.

"And if the airlines are going to provide something like that to me, then it even causes me to wish well for them."