There should be a Tell HN that is just an 800-comment-long thread full of these stories because I love them.
As gratifying as they are, they get repetitive. Once you've heard one, you've heard them all.
I'd much rather hear about the place that fixed a policy problem that was blocking such progress in the first place. Software is easy, getting people (and orgs) to change is hard, tedious, boring, but absolutely necessary, and more enduring than a lot of software fixes.
He really, really loved administrative law.
Although I was a lawyer, and I can tell you that human beings come up with an infinite variety of ways to do weird things, which gives me hope that there may be a weird software story out there for you, that you’ve never heard. :)