For your [in]convenience: How some airlines are trying to stay ahead of your inevitable frustration

A couple of recent experiences with Air Canada taught me a valuable lesson: In today's environment, don't mess with Airline Mother Nature Bot.

I know intimately how aggravating it is to encounter a delay and a missed connection, not only as a current traveler, but also as a former airline employee. I used to see the angry and distraught faces so regularly that I knew what was coming my way as soon as our eyes would lock from a distance – daggers, pitchforks and the sharpest tongues ready to slice up your self-esteem into bite-sized pieces that could fit into those little food bags people were taking on board. You really had to rely on your instincts and expertise to navigate out of a tough situation because those were the days before smartphones and apps and airline fact-checking. Your word carried the weight of a 747 and you had to "stick the landing," so to speak.

If you got a smile and "thank you" in the end, that was enough of a reward for something that could have gone so terribly wrong. I used to think about how an airline could better anticipate such predictable circumstances and have solutions waiting before the inevitable passenger-agent clash. Back then it was up to policy, agent expertise and discretion. Today, it's in the hands of technology.

Remember those long lines at the service desk filled with desperate passengers trying to rebook flights? Sorry to say, they still exist. But airlines are making strides in getting away from a model that's inconvenient, inefficient, and at worst, confrontational. Armed with smartphones, we've become accustomed to having so much at our fingertips that we've convinced ourselves that we're our own best travel agent. In most cases, especially for simple trips that happen to go as planned, this might be true, though I'm also convinced that nothing beats a really good, trustworthy flesh-and-bones travel agent, especially when your plans get hosed. Lacking that, technology has done amazing things with booking, check-in and even baggage tracking. Instant flight notifications keep our eyes on our screens instead of the departure boards and they keep those inaudible delay announcements at the gate to a minimum. But when it comes to getting your flights rebooked after schedules go awry, some airlines are going with automatic rebooking "bots" and you might not realize it until you try and mess with it.

I was on my annual pilgrimage to Halifax, Nova Scotia last year (I worship lobster dipped in Dairytown butter so yes, it's a pilgrimage). The flight from DFW was delayed enough that I was going to misconnect in Toronto. The check-in agent told me they'd take care of things there. They really didn't have the ability to rebook as they were not Air Canada employees and were restricted to whatever the check-in system would let them do. My initial skepticism gave way to acceptance. So, I checked a bag. I usually try not to but I was carrying some items that couldn't be carried on. OK, they were bottles of wine for my kind host waiting in Halifax. I hoped that things in Toronto would right themselves once I got there. At the DFW gate, I called the airline to see if I could get on a later flight to Halifax since the Air Canada app gave me an ominous "cancel check-in" warning as I attempted to make the change myself. Maybe I shouldn't mess with this through an app, I thought, so I called and was rebooked on a later connecting flight. Problem solved, right?

Once I got to Toronto, the agent meeting the flight handed out new boarding passes to connecting passengers. I gave him my name and after a little rustling of paper and shuffling through boarding passes, he gave me a blank stare. When I said I had rebooked myself on the later flight, I got the scolding: "Why did you do that? We rebooked all connecting passengers automatically. Did you check a bag?" I nodded, and then got more pursed lips and furrowed brows from the agent. "You're going to have to get your bag here in Toronto," he said. I asked what I could do at that point and he whipped his arm in the direction of the service desk with the off-putting gesture of a dog owner banishing his misbehaved pet to a corner.

After my mini walk of shame for doing what I thought was proactive, the service desk informed me that I couldn't take the flight I had booked myself without my bag. The bag would have to be retrieved and rerouted onto the correct flight. I completely understood the rule that international bags have to travel with the passenger, but what I didn't get was how my new itinerary did not trigger an automatic reroute of said bag since it literally was sitting beneath me in the cargo hold as I was being rebooked. It turns out, the airline was trying to be more proactive than I thought I was. Their system had automatically put me on an alternate flight, with my luggage, only this flight was even later than the one I had booked.

The agent at the service desk gave me instructions on how to get my bag rerouted (it involved yet another service desk), then she gave me some advice: "Let the system do its thing." Apparently, the moment you mess with it, things tend go haywire. The good thing about being automatically rebooked was that I wasn't scrambling for a flight once I got to Toronto and I didn't have to stand in a long line wondering what my options were. The bad news is that I felt like I had no choice. When your fate is in the hands of an automated rebooking system, even if an earlier flight is available when you land (maybe your original one out of some miracle), you can't do much if you've checked a bag. I messed with the system and now had to get the airline to dig for my bag and re-tag it.

Fast-forward to this year and, once again, my escape to the cooler, salty air of Halifax in June was challenged by flight issues. This time the flight from DFW was 4 hours late and counting – a definite missed connection. I remembered the reprimand from last year and decided to "let the system do its thing." I got a text notification of the delay, then shortly after, a new flight notification. But this one was for the next morning! I was getting into Toronto too late to make not only my original connection, but any subsequent flights that night because those were fully booked. I called the airline to confirm that indeed the first available flight to Halifax was the next morning. I asked about overnight accommodations but got no clear answer other than, "you'll have to check with the agents in Toronto." I then got on Twitter and sent a direct message to the airline. Sometimes, it's the quickest way to reach them because the last thing they want is someone ranting publicly about how horrible things are. I was politely sent a link to the portion of the Conditions of Contract with respect to delays and cancellations. The airline commits to providing overnight accommodations on international flight delays within their control of more than 8 hours, but it wasn't clear whether that meant a single flight delay or an entire itinerary. Was it purposely vague to give the airline an out? That's what my jaded mind was thinking. This was a mechanical delay, fully within the airline's control, so at least that fact was on my side. I would be getting into Halifax a full 11 hours late but my original flight was only 4 hours late. Why couldn't anyone give me a clear answer? "Let the system do its thing" rang in my head. Having looked at what I would pay for a hotel near the airport, I realized that there were enough online deals to get a decent price if it came to that. I was happy to be going to celebrate Canada Day and the 4th of July and if this delay was the price to pay for peace, comfort, great weather and lobster, so be it.

Upon arrival in Toronto, there was still one flight left going to Halifax. Maybe by some miracle it had open seats, I thought. I went to check at Ye Olde Service Desk. You know the one. It's the airline's version of a pub where the downtrodden travelers spill their sorrows and surrender to the forces pushing down on their souls. "But your bags," I was reminded. I guess I was stuck for the night after all. Once I handed the agent my old boarding pass so I could get the next morning's one, she handed back a nice surprise. It was a ticket jacket with the airline's compensation policy, along with my new boarding pass, plus a hotel voucher for a night's stay, plus dinner that night and breakfast the next morning. I didn't have to ask.

In a world where everyone claims to know everything and a reputation can change with a single video upload, airlines are trying to stay ahead of tough situations by tapping into our obsession with technology and using it to ease our minds during schedule disruptions. It's not a perfect system yet, but I get what some airlines are trying to do. I've also learned that Air Canada does indeed let you pick another available flight from the one chosen for you using their Delayed and Cancelled Flight Service. Maybe the third time will be the charm but it's got to pass the baggage reroute test. Honestly, I'd simply be happy with an on-time departure next time. Hey, at least they're trying to deal with the reality of congested airports and flight delays before people regularly storm airports screaming the famous quote from the classic film Network: "I'm as mad as hell, and I'm not going to take this anymore!"

That quote came from the lead character Howard Beale (played by Peter Finch), a news anchor at the end of his rope who aired his frustrations with the world on live television. It was great for ratings until he began to criticize the corporate overlords of his network. Beale was sternly warned about his antics by chairman Arthur Jensen (played by Ned Beatty) who bellowed: "You have meddled with the primal forces of nature!" The point was that it was fruitless to fight against the immovable global corporate structure Beale was railing against.

In some strange way it reminded me of my plight as I marched (in my head) with that same "not going to take it anymore" attitude to get justice for my flight delays. No matter how much I wanted to scream with clenched fists, I was reminded that sometimes, I just had to let the system do its thing, and meddling with the forces of Airline Mother Nature Bot was indeed fruitless – at least this time.