For IoT devices/cell/etc it could be 'bad' to give out the root password from a company PoV. As there are so many out there with the exact same password on several thousand devices (poor security but you can image a thousand devices in a few hours). So once given out it is written down into some wiki and everyone has it now (welcome to the botnet). So if you get one change whatever you were given and assume everyone else has it. Or maybe the 'secret sauce app' is under some random user account. But give out root and that special secret account is bypassed. Then it is off to china somewhere to be ripped apart and resold under a new brand name and half the cost.
Then on top of that lets say you are a nice company giving the thing out. That means you will need some sort of training for your support guys. Documentation on how to do it. And so on. Those things cost money for a EoL product you no longer make anything on.
Like I said there is a list of things as to why not to do it. There is also an interesting list of why to do it. But the upside is low for the company to allow it. I wish more companies would do it. But it is rare.
If people want companies to do this, the company has to be incentivized to want to spend any time/money on it. If people can make this an upside to companies doing this and not 'shame' and 'you broke the law' the companies will help.
It does seem like there ought to be a reasonable split between personal software and business stuff. I mean you guys had a big contract, it is some negotiated thing between two peers, it could be reasonable to negotiate root in some subsystems, not in others. In the end you can’t really trust anything a system tells you if somebody has full root of it. It seems like you guys keeping control of the logging would be a reasonable give for them, if they expect support. (But why would you guys have planned around a downright adversarial customer? That guy is weird).
Also, doesn’t this seem like… basically some kind of fraud? I wonder if your annoying user expected to be able to add the savings whatever he got back from the support contract to his “value to the company” somehow.
For personal customers who are just buying smartphones, we don’t really have giant support contracts to screw around with.