Soooo.. Haven't seen anyone ask this. Why DOESN'T he want it updated? Have you checked for running processes, keyloggers (hardware and software), hidden partitions, Veracrypt, etc?
There may be a reason that's not being shared.
Otherwise I agree with the email routes that get it in writing (or the lack of response as such).
It’s a medical office, $100 says it’s running some outdated software no longer supported by the vendor but must be kept n in operating state because HIPPA requires you to keep patient data of children available until they’re like 25
Some IT bosses aren’t great at communicating why, they just want to stop the convo on things they can’t fix and resume working on progressing things they can
This probably applies to bosses in any role. That said, this boss is not an IT guy, he's a manager in a "health" business employing an IT guy. Why wouldn't you tell the IT guy you hired about your IT requirements?
Walmart is also a family owned business, that term means nothing in regards to company size and org structure. In another comment OP says there are several leadership tiers including managers, directors, and VPs, those org charts don’t exist in mom&pop health clinics. If OP is a one man IT department then this company is grossly mismanaged and is being negligent with their data by hiring a singular kid straight of college to be their IT department, if he’s one of many like they should be then OP is just a new-hire that needs to pump the brakes and learn to follow direction