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Edit Admin
Sorry to say that Tim is the WTF in this one. Company IT is a bit of a WTF for needing to schedule a meeting to discuss giving someone more disk space (where I work, we just have to open a ticket, though we do have to include a sentence about why we need it), but IT definitely isn't going to just accept some hard drive from someone to connect to a company computer.
It's also Tim's fault for letting it become an urgent problem. Either he was slowly using up the disk space and wasn't paying attention to how much he had left, or he really did absolutely zero planning for how much he would need (or at least whether or not what he already had would be enough).
Admin
Honestly, this whole series reads like the story of a coding cowboy riding in from the wild west of home development and into the big city of corporate life and finding out, to his shock, that there are these things called rules and procedures that must be followed. Seriously, like, has he newer heard of a little thing called accounting?
Edit Admin
And more to the point, Coding Cowboy is riding into the world of heavily regulated corporate life. The regulators want to know that you know where all your equipment came from, and that you've done some vetting to make sure they didn't come with malware preinstalled. The bigger you are, the worse it gets, because every additional country you do business in adds a new set of regulations and regulators interpreting them, and you have to follow the least-permissive union of all of those regulations.
The real fun is when you work in IT security for such a company, and your job is to pretend to be the bad guy to find holes in your defenses before they do. In that case, your life involves constant explaining why you need to do X even though it's contrary to policy, because the bad guys aren't constrained by the policy that says you can't do X. You can't determine if the controls that are supposed to keep you from doing X at all are working, if you're not allowed to even try doing X. Add a regulation that says you have to do such testing, and you're deep into the world of Catch-22.
Admin
I deal with users like this all the time. It's always interesting to guess when they'll calm down and figure out how to work with the system.