There's a point in time where you're crossing the boundary from mistakes into the realm of unlawful activities. I think it's very difficult to argue such action

There's a point in time where you're crossing the boundary from mistakes into the realm of unlawful activities. I think it's very difficult to argue such actions are a mistake (e.g. "I had no idea insider trading was wrong, your honor, it was a mistake!"), because such things are an entirely different class of behaviors. They're intentional, and if such intent can be proven in a court of law, they are usually tried as such. Proving intent is exceedingly important in criminal law. If you're looking for mistakes that can bring material harm to others, it might be easier to examine industries where errors in judgment lead to physical and/or financial harm. Transportation industries (aviation, trucking, etc), construction, and a whole slew of others offer a variety of examples to choose from that don't necessarily require intentional misuse of resources to cause harm. Think of how many aircraft accidents have occurred over the decades as a direct consequence of mistakes made by the air crews--or controllers, or maintenance staff--and were, frankly, errors in judgment. Sure, there have been cases where maintenance shortcuts were taken to either save money or time, lead to the deaths of passengers and flight crews, and have been successfully tried in a court of law as negligence (or worse). But that clearly crosses what should hopefully be a distinctive line into unlawful actions, and even still, there have been circumstances where the maintenance staff wasn't held accountable. Again, it's a matter of intent. So I think context is important. In the case of Microsoft, I don't think that the mistake in question should result in wanton firing. Perhaps if someone could prove that they were materially harmed by the upgrade, then it might be pertinent to seek damages from the company. But oftentimes the developers on staff either did something wrong (and fixed it) or were specifically told to implement that feature by management. Everything else just seems like splitting hairs.