To me, "problems connecting flight crews to their schedules" does not clearly say it's a software issue, but maybe implies it. But you have other information that it is?
Any info on the details? Like, I'd think this is what scheduling software is for...
I feel like this is a good illustration of the problem with "eh, why does technical debt matter, everything is still working isn't it?" It is, until it's not. And then it's too late.
