Stuck on the tarmac in the snow and miss the connecting flight (last of the day)? They automatically rebooked me on another airline and I got a notification from the app as soon as I had reception.
3+ SFO bound flights delayed at JFK because of crazy winds at SFO? They proactively encouraged people to rebook, gratis. I rebooked on a flight the next day on nicer equipment, through the app, went into town, grabbed some bagels and had a flight at a nearly ideal time of day.
Regional plane goes tech? They had a red coat out and about keeping everyone informed.
Missed a flight because I misread the departure time? They sold me a same day ticket on the next flight at a hefty discount and I kept the inbound leg.
Southwest has a huge disadvantage and it's not tech: it's the lack of interline agreements. Nearly every other airline (except perhaps Spirit) can rebook you on another carrier when things go sideways. Southwest simply can't. With an interline agreement in place you'd have far fewer people getting stuck with exorbitant last minute fares.
In general though don't fly when you're getting unusual weather. Less than an inch of snow at PDX throws everything into chaos (and Portlanders call it fucking snowpocalypse). A few inches of snow at PWM and they don't even blink.
I should also add that a few years back when my Southwest flight out of SFO got cancelled I was able to book a seat on a flight out of OAK with a minimum of effort. I think I had to pay the difference in fare though. When it works, it works, but the go it alone attitude will only take you so far.
Maybe not 1:1 for what you're describing, but it solution/reason, but does seem like a possible sign that they're investing in proactive tools.
AA live chat said they couldn’t help (other than rebooking 2 days later which would be pointless) but when I called they were able to drop the connection inbound and outbound so I could drive to the hub city airport (cost me like 2 hours each way, nbd).
They fixed it in like 3 minutes on the phone but it seems like they have to do it in a super hacky way because I had to check in at the airport which was no fun with long holiday lines.
Consider: when a flight is delayed for a repair (maintenance delay) does that equal "not enough aircraft"?
Carriers can't staff surplus crews any more than they can sit on spare aircraft, both which are small, very carefully computed quantities.
It is a crew rest requirement delay.
If I’ve had a missed connection en route, I’ll generally land and the app tells me what they’ve already rebooked me onto, but I have a choice of many different alternatives (usually) and can pick among them without cost and without waiting in a call queue.
Delta does this well too. Haven’t heard many good things about American.