At this point I’d take the malicious compliance route. Make sure you have it documented in a form of writing that shows he is refusing to upgrade his system. Send him an email confirming you the new laptop on standby and would like to know when he’d like to swap it out, he’ll obviously tell you to pound sand. If anything happens, it’s not on you. If you’re worried about getting fired, then it’s not worth it to pursue.

Your boss is aware of the problem and doesn’t want you to leave a clear paper trail about it in writing. Think about that a little bit.

Welcome to IT.

Fellow IT guy here (welcome!). It’s like everyone else said: have some proof that your boss was informed of the situation. As someone who worked for a few years in IT: avoid verbal agreements; you won’t be able to prove they happened and they’ll make it your fault. As an example, I refuse to do any work that might have long-term consequences if I don’t have a ticket requesting as such or at the very least a mail in my mailbox. All agreements should be documented somewhere. Email is good, hard copies (paper) are even better.

Always, always, always document your requests. Bosses will not hesitate to throw you under the bus when something THEY fucked up goes wrong. Like southsamurai said: cover your ass, then follow orders. When shit inevitably hits the fan, you’ll have something to point to.

I would absolutely send him an email to the effect of

“Per our multiple verbal conversations, this is just to serve as notice that, in my professional opinion, your refusal to allow me to upgrade a system at risk of multiple security vulnerabilities on a platform that is no longer supported is a risk that you are choosing to accept against my advise.”

with a list of known major vulnerabilities attached if possible.

That way at least if this comes back to bite the company on the ass, he can’t say “Well he never told me this was a problem!”

Cover your ass, then follow orders. The job is, whether anyone likes it or not, to do what a supervisor tells you. If the supervisor is an idiot like yours, that doesn’t change. Do the job, cover your ass, and hope for the best.

Doesn’t sound like it needs web access to function. Block web and all other ports at switch/core/firewall etc.

Start looking for a new job. Don’t wait until you have certs, just look. And don’t describe this situation in any interview. Just say you’re looking for growth and new challenges

A couple additional thoughts:

• You sent your boss an email using your company email server. You do not control this server. You cannot rely on this email as a paper trail, any email you send could be deleted by someone else with administrative access. In Outlook it’s possible to delete any email that was sent internally and the logs that it was sent.

• You should write down the date(s) and time(s) that you sent emails about this to your boss, on paper. Keep it with your other work notes.

• You should not include any specific technical information about your company’s systems in this paper record as this might expose you to liability in the future. Just record when you sent the emails and a general description of the subject (e.g. “email to boss about upgrading out-of-date operating system”), and a short description of any response (verbal or written).

• You have offered to upgrade this system. Your boss said no. It’s not your responsibility anymore.

• If I were in your position I would tell my boss explicitly that I won’t be responsible for the security of this system or anything connected to it, at least not without a signed risk acceptance statement. You might not feel comfortable doing that, it is potentially confrontational.

• If you’ve been told that you’re responsible for this system (your employment is dependent on it) in spite of your objections, please take a look at this article about security hardening for Windows 7 and try to implement as much as you can. If you’re not responsible for it, don’t mess with it.

Windows 10 will be in the same boat again in about a year and a half when Microsoft drops support.
Do you really want to have this fight a second time trying to get him to upgrade to Windows 11?

You’re not employed to fix all the problems, you’re employed to fix the problems your boss wants you to. Save the emails where they deny your concerns for the inevitable subpoena but other than that shut your mouth on this topic and move along to other tasks.

Edit: further note since you’re new to IT. HIPPA requires that orgs keep patient data of children in an accessible manner until that child is around 25 iirc. When I first started in IT we still had a couple 3.1 and 95 machines running an old out of support EMR software until the patients in it were old enough we could pitch it. It’s entirely possible this is the reason your boss is keeping this machine, it may not be upgradeable because the software simply doesn’t work above windows 7. I will say there’s merit in moving that data local to the machine and getting it off the internet access though. But if your boss says leave it then leave it.

It’s your first IT job and you’ve been there for a few months? While your safety concerns definitely can be relevant my advice is this

You should

1. Don’t rock the boat as a new hire. Figure out what is going on first. Maybe there’s a reason to some of the madness you see.
2. Do NOT contact the owners. Doing so will likely be seen as disloyalty by your boss and possibly the owners as well. Only go through your immediate superior.
3. Don’t bring it up again with your boss. It’s not your responsibility.
4. Leverage the user. Let the user be the one to push for a system switch.

You could

1. Figure out if you can get the system on a separate VLAN and get it locked down in firewall rules.
2. Research the system. Why don’t your boss want it replaced? Does it run some ancient software? We’ve got some machinery that is running windows 7 at work. When I got hired, in the days if windows 8, the controller was running windows XP. The setting up of drivers and archaic proprietary software, involved in upgrading, is immense. When we switched to 7 this €60k equipment was down for days, and it was a week before it operated properly.

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).

deleted by creator

The most chaotic good thing to do would be to use the known security issues to hack into your boss’ computer in the most scarry looking but harmless way. That would possibly scare them into upgrading.

With that said, you should create a paper trail on how you warned your boss, and either wash your hands of the issue or kick it up the chain, depending on how much you care.

EDIT: since it seems some people didn’t get it, I meant the first option as a joke. My actual advice is the second paragraph

Something I haven’t seen mentioned yet - who is the company’s HIPAA “Compliance Officer”? If it’s anyone other than your boss, you could document the situation to them in an e-mail. If you want to be slick about it, ask them if there is “still any compliance need to keep the replacement machine ready or if it would be OK to repurpose it, given [your boss’s name here]'s decision not to move forward with the upgrade.” They’re on the hook for compliance violations, so they’ll likely see to it.

I would also suggest making a habit from now on of documenting verbal conversations that result in actionable decisions in short e-mails to the other party: " To recap our discussion, [bullet point list]"

You can excuse this as being for your own reference so you don’t forget any to-do items or so that they can correct any misunderstanding on your part, but it makes for a fantastic CYA if that ever becomes necessary. For really important items likely to bite someone later, print a paper copy if you don’t fully own and control the machine AND the e-mail local archive. Only bring those out if absolutely necessary, as in when SOMEBODY will be fired or you’re about to be legally scapegoated. They’ll save your butt once, but it will probably be time to start looking for another job because the boss will think either that you should have pushed harder earlier to fix the issue or be worried about their inability to scapegoat you in the future.

an email I sent to my boss about upgrading was never responded to

Dear Boss,

As per our recent discussion [blah blah]

Thanks for allowing me to leave early on Friday for my appointment.

HnK,
 -Staffy McStafferson

When you get a ‘brown M&M’ response …

Staffy,

I don't remember the discussion about Friday.  

-Jefe Jefenbaum

Then you know you got 'im.