Asklemmy

Figure out how your boss is ripping off/stealing from the company with this outdated system

to emphasise something missed - you said the employee using the old machine asked for an upgrade?

make sure you have it in writing. from them, in a full clear email, what they want and exactly why they want it. They need to be verbose enough to cover every point. (it's okay to secretly help them, but do NOT have your fingerprints on it).

Then, reply and forward that email to your boss, with your professional opinion of their request and their reasons for it.

Include cost for proceeding, and what the costs will be for doing nothing.

Acknowledge that this matter has been spoken in person, an apologise for the informal tact; that this email is intending to follow proper procedure, which you will continue to do in the future.

Ask to confirm their response so you can officially deal with the matter one way or another.

The main thing to add, to clarify: you are the middle man. Don't make it look like you are the one wanting to do this. The employee is. You are wanting to do your job, which is dealing with problems that are brought to you.

you can advise but the boss man has the final say

"This is my first IT job, I’ve only been working here 3 months"

Then you need to learn this lesson quickly: YOU ARE NOT THE BOSS. The Boss is the Boss. Not you. You make your concerns known to him then you leave it at that.

"I’m considering talking directly to the owners about this issue" Yeah, going over his head is really going to go down well /s. As you have proven you are hard of learning, let me state clearly: it won't, that was sarcasm. The owners will see you've gone over your boss's head and when he says "I've had enough of this jerk, let's get someone else in" they'll be hard pressed to disagree with him.

"my boss’s refusal puts our operations at risk" Your boss already knows this. Especially as you keep banging on about it. What you're doing here is heading for an unceremonious out-kicking. Your boss also knows a lot more about the business than you do. If he's keeping that machine on Win7 then he probably has some good reasons to do so.

"I want to ensure I handle this professionally" No you don't. You want to force your boss to do what you think he should do. If you were being professional you'd state your concerns, in email if necessary, then move on.

"I definitely feel like I’m going to be used as a scapegoat" That's why you put your concerns in an email (ONLY to your boss, nobody else. Or maybe a sympathetic team member). This creates a paper trail so that if and when they come knocking on your door saying "Why did you let this happen! You're fired!" you can point to that email which proves you did everything you could. (Which they won't by the way. You're an idiot newb three months into your first job. You don't have any responsibility yet. So this isn't on you.)

"I’m also planning on seeking employment elsewhere" It doesn't matter where you work while you have this attitude. Newsflash kiddo: you're the asshole here. You're a newb three months into your first job. No matter what you think you know, you don't know anything. Instead of trying to dictate to others what you think they should do, try to learn why they're doing it differently from what you expect. Maybe you have to find somewhere else now; that boat may have already sailed. Maybe if you approach your boss saying something like "er, sorry I was an asshole, I thought I knew more than I do, can we start over and I want to learn from you" (but obvs phrase it better than that) then MAYBE you stand a chance of getting through your first year.

[Sympathetic mode on.]

We all have to learn this stuff and it takes time. Your boss also knows this, and remembers when he was an overenthusiastic hothead. So while all the above might seem harsh, especially the YTA bit, hopefully it'll cause a course correction (which is my intent here) and you'll be back on track to a successful career in IT. This position may still be salvageable but you need to go in on Monday understanding clearly that it might not be, and that it is your fault. And maybe you need to be fired a few times before this sinks in. Good luck.

You've done your part.

Now send an email that states that you understand that he doesn't want to upgrade computer with asset tag X out of Windows 7, despite the security concerns and crashes, and if this changes, you have a windows 10 desktop ready to deploy when/if the time comes, then thank him for his time.

Edit: oh, and file this email (and any responses) in an easy to find place, just in case.

E2: also, windows 10 is EOL soon, so you may want to upgrade the new one to 11 if the software works with 11. And make dang sure the software works. The vendor's word might be misguided. It doesn't work, until you verify it works.

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.