Asklemmy

Just post the IP address and we can sort it out for you.

Back everything up first and you will be their hero.

CYA at this point. Email the relevant info to your boss, bcc a non-company personal email, or print out and store a copy of the email for reference. When shit goes tits up, it probably won't save your job (big IT event like that usually kills a family business), but it will save you from getting sued or smeared for the catastrophe.

I grew up as the "IT guy" in small town America.

This guy, and the people here (not you) sound like a lot of people I know. I'd look for a different job and grow your passion somewhere else. It isn't worth it. You won't change them, and they're just going to make you feel like you're wrong, even though you're right. It's like the movie Idiocracy.

There should be no issues as long as he doesn't access the internet directly. If you have a terminal server you should be able to set up any web browser and let him use it in a remoteapp mode.

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).

Just curious, what are his reasons for not wanting to upgrade?

Leave it until the system fails then when things go tits up you can tell the owner that you knew the problem was coming and gave multiple warnings to your boss about it and he shut it down.

Ah yeah just like the other post, make sure there is evidence.

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!"

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

What a disaster. Post IP and system information on 4chan. He will switch after being compromised.

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.

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.

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.

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.

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?

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.

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.

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