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.

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

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.

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?

Windows 10 is just about to lose support. At this point, your backup system should probably be Windows 11 unless you can manage to make your boss fork over money for updates. Otherwise, you’ll be stuck in the same situation in just a year and a few months even if you manage to replace the system.

Make sure you go full CYA mode when your company eventually gets hacked because of your boss. Leave a paper trail that’s not too hard to discover for any auditor in case your company ever tries to get some kind it certification. If you have a ticketing system, leave an open ticket. Put any further requests in writing, possibly referencing company poollicht about this stuff if you have any.

Next time you take an inventory it outdated and vulnerable software and hardware under your control, make sure to add your boss’ computer to the list and send it around to everyone that should be reading the report. Preferably, more than just your boss and you, but that depends on how your company works.

Your just boss isn’t going to update willingly. If you can’t make him update, the second best thing is to leave behind evidence that you tried to avoid the disaster your boss is brewing, so he can’t blame IT when his laptop gets hacked or if he loses data. Because when your company is getting sued for a data breach, you’ll be one of the first people they’ll try to put the blame on.

You need a new job.

First few months in IT? Welcome to hell…

I’m kidding (mostly), I’m in IT also and if you’re in for even a few years, you’ll start to build a collection of horror stories like this one. We’ve all seen things you wouldn’t believe.

So you need to have full buy-in from the owners. If you’re able to talk directly to them, then it sounds like this isn’t a huge company. If you clearly explain in a professional way to the owners the situation with documentation and they don’t fully support you, leave the company asap.

As somebody who has been involved in multiple ransomware recoveries, trust me…you don’t ever want to deal with a rogue unsecured machine on the network. And owners that don’t care or take that risk seriously are absolute fools and this will only be the tip of the iceberg of stupidity.

That computer is a ticking time bomb. Please for the love of God tell me that your boss doesn’t have local admin rights on his system.

If the only thing your boss uses that system for is to connect to a web app to manage inventory, why is he mad about switching from windows 7? Does he just like how windows 7 looks visually?

I guess it doesn’t really matter. Also, windows 10 isn’t a long term solution because it also goes EoL next year in October, so you’ll be in this same position in less than 2 years.

You can either go to Windows 11, or if you wanna be a little wild, install a Linux distro like Mint on there and theme it like Windows 7. You solve the security problem and he gets to pretend he’s still in the early 2010’s.

Honestly though, start looking for another job if the owners don’t support you 100%. IT is already a stressful and intense enough job, you don’t need stubborn idiots like your boss to add flavor.

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.

I don’t have advice, just a worthless anecdote.

I work at a large tech company. We had a Windows XP system on our network get hacked. They used that to jump to our servers. IT had to quarantine off the whole lab, because they didn’t know where the hacker had hopped next. So then IT had to do a post-mortem and figure out how they got in and what was affected. That process took 3 months. In the meantime, any team with servers in that lab couldn’t use them. The team directly responsible for this couldn’t work at all for the full 3 months.

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.

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.

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!”