I have a similar length of experience as you, but I'm on the opposite side of the fence and side with the students in this case. If an organization is willfully putting out and maintaining shit products year after year and equivocating about how updating things to be more in-line with modern practices is oh so difficult and oh so expensive, maybe they do deserve to be mocked. If they're making an effort, that's a different story. There's really no excuse to keep insecure and outdated things out in the wild except for organizational laziness. Stand behind and maintain the crap you sell or don't sell it at all.

I think as a profession we need more derision and mockery of poorly made, documented and maintained shit and less reverting to robotic response of "you just don't understand, man".