September 21, 2026 at 2:35 pm

A Tech Worker Was Updating All The Computers, But His Supervisor Refused To Let Him Replace One

by Jayne Elliott

businesswoman arguing with businessman

Shutterstock

You know what’s tricky with technology? Updates. Updates are tricky.

For example, if you get a new computer, it may not be compatible with the software you were using on your old computer, and that can be a big problem.

In this story, one tech support worker was in the process of replacing all the computers in the office with new machines, but there was a tricky situation with one computer due to a program it was running.

The worker’s manager told him how to handle it, but another manager was furious when she found out what he was doing and demanded that he not replace the computer.

Keep reading for the whole story.

That time I got threatened with termination by the CIO for trying to do my job

This goes back to 2019 when I was working on a mass workstation refresh to get everyone off of the 10 year old Windows 7 PCs and replace the with modern Windows 10 systems.

This was partly because Windows 7 was now EOL, and also partly because the new ERP system was not certified for use on Windows 7.

If it wasn’t for the ERP upgrade, the Windows 7 machines would probably all still be in service to this day…

There was a problem that needed to be solved before replacing the last machine.

I had replaced all but one machine (out of approximately 110 in total) at this point.

The last user was the one person in the entire organization that was using QuickBooks to track finances for two of the companies subsidiaries.

Of course, since his machine was 10 years old, he was on an equally old version of QuickBooks that not only did the company misplace the installation media for, they also no longer had the product key.

And as it was EOL, we were SOL in getting any support from Intuit without paying more than what a new version would cost. I also learned that that version wouldn’t run on Windows 10 even if we did have a way to reinstall it.

They came up with a temporary solution.

Given this dilemma, and me being on the bottom of the org chart, I deferred to my manager regarding what to do.

He had asked me at least three times to get him prices for a new license to QuickBooks Enterprise, but balked on the cost each time.

Ultimately we reached what was supposed to be a temporary compromise where the Windows 7 machine would be pulled from the user’s desk, a Windows 10 machine installed in its place, and remote desktop set up on the Windows 7 machine for him to remote in and do the QuickBooks work on the old system.

I worked with the user on scheduling a time to do the swap out while he was going to be out of office for a few days and a time that I could show him how to remote in to the Windows 7 box when he got back.

The finance guy’s supervisor didn’t seem to understand.

I got as far as setting up the Windows 10 machine in the lab to copy his documents, desktop icons, bookmarks, etc. from when his supervisor got word that I was in the process of replacing his computer.

After explaining to her the workaround regarding the QuickBooks I got the impression she didn’t listen to a word I said.

She went on a rant about how I was not to touch his machine without her permission.

At this point I continued on with the file transfer and notified my boss who said he would address the concerns. I didn’t hear anything else, and proceeded to schedule a date to do the swap.

OP decided to ignore the machine’s rant.

Right after swapping in the Windows 10 machine, but before getting remote desktop set up on the Windows 7 box the Karen manager started ripping in to me for not listening to her and ignoring her and being insubordinate.

I told her to talk to my supervisor as we needed to get rid of the Windows 7 machines due to security concerns and that Windows 7 was not compliant with the new ERP system.

Cue a story from her that when the new ERP system goes live it will have the ability to import directly from a QuickBooks file.

I walked away and proceeded on with my kludge of a workaround as that is the order I had from my supervisor and sent my supervisor an email note detailing the encounter to which I got no reply.

Karen’s not letting this go.

The next morning my boss comes to me saying he has heard a complaint from the Karen manager.

I recounted what occurred and he again promised me he would look into it. He also stated that the Karen was mistaken, and that while possible to import accounting records from QuickBooks into the new ERP system, it was not a simple task and the same capability exists in the old system too.

I went on about my business until early afternoon when one of my co-workers took a phone call from the CIO.

In this phone call, the CIO was not happy as Karen manager had escalated the complaint to him.

The CIO sided with Karen.

My co-worker didn’t know what the ordeal was about and I told him it what it was regarding and he transferred the CIO to my phone.

I tried to explain that we had a workaround to the CIO and that we needed to get him off of the EOL Windows 7 machine, but he went on a ramble about how Karen was reporting that I was refusing to do my job.

I tried standing my ground as my manager was the one that OK’d the swap and workaround, but he demanded that I put the old Windows 7 machine back in place, and casually mentioned that he would consider termination if I continue to ignore orders.

He made a decision.

After the phone call ended, I discussed the situation with my co-workers and tried to reach my manager, who had conveniently disappeared.

Since the CIO was demanding it, I put the Windows 7 machine back in place and updated it as much as I could. …and there the Windows 7 machine sat, in service, up until the day I left at the end of 2020.

I quickly noticed after this that my boss had a habit of actively avoiding this Karen of a manager. I had even seen him drop what he was doing and slip out of the back door to the office when she would walk in.

I guess maybe the Karen manager was right? She got her way, and I guess there was no harm done since the machine stayed there for a long time.

Let’s see how Reddit responded.

This person rants about management.

2026 09 16 at 12.08.04 PM A Tech Worker Was Updating All The Computers, But His Supervisor Refused To Let Him Replace One

Another person thinks this will eventually end badly.

2026 09 16 at 12.08.14 PM A Tech Worker Was Updating All The Computers, But His Supervisor Refused To Let Him Replace One

This person calls out OP’s boss.

2026 09 16 at 12.08.34 PM A Tech Worker Was Updating All The Computers, But His Supervisor Refused To Let Him Replace One

Another person shares how they react when they’re threatened.

2026 09 16 at 12.09.03 PM A Tech Worker Was Updating All The Computers, But His Supervisor Refused To Let Him Replace One

It has to be annoying to be caught between differing opinions about how to handle a situation. OP was only doing what his boss told him to do, but I guess what the CIO says trumps what the supervisor says.

Doing your job can be complicated when management disagrees.

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Jayne Elliott | Contributing Writer, Life & Drama

Jayne Elliott is a contributing writer and editor for TwistedSifter specializing in human interest stories, internet culture, and family dynamics. With over 12 years of editorial experience in digital publishing, Jayne excels at analyzing complex online communities and transforming viral social debates into thoughtful, highly engaging narratives.

Rather than simply aggregating internet drama, Jayne brings a sharp, empathetic editorial eye to everyday dilemmas. She has a unique talent for unpacking the nuances of pop culture and online conflicts, providing readers with relatable, well-researched commentary.

Based in California, Jayne spends her free time outside the newsroom exploring theme parks with her family or beach-combing along the coast.

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