July 14, 2026 at 6:15 am

A Defired IT Specialist Is Laughing After His Former Company Hit the Emergency Button

by Benjamin Cottrell

man in plaid shirt working at his laptop

Pexels/Reddit

Some managers keep in touch with former employees out of genuine appreciation. This one reached out purely because he couldn’t locate a single file.

Two months after being let go, one employee received an unexpected email from his former remote boss, sent straight to his personal address, asking for help locating data he had already properly transferred to the company’s shared cloud system.

But instead of accepting IT’s explanation of proper protocol, the former boss continued to push boundaries.

Now the employee is wondering how much he owes someone who unceremoniously kicked him to the curb.

Keep reading for the full story!

Continues to reach out and ask for favors, I was let off months ago

For the past couple of months, it was just me and the boss. He was a remote boss (we met maybe once every three months), so he would write emails on what needed to be done and then we’d do it, essentially, without having any clue whatsoever about the actual business.

Soon, this employee was force to kiss this job goodbye.

Well, apparently he thought he does, because he found someone to replace me (and he couldn’t afford us both), so I was let go 2 months ago.

So he went through the motions and followed the rules as closely as possible.

Before I left, I did everything as per protocol. I wiped the computer of all my data (to prepare it for the other coworker), and transferred it to a cloud service that was shared by the members of his group (which, mind you, it was only me at this point).

It is sort of standard practice at the workplace to wipe the computer and then put the data in the cloud, so I figured it would work itself out.

But the boss wasn’t at all on the same page.

Then the new employee started a couple of weeks ago. So the boss apparently asks IT to just allow her access to my computer, thinking that I had just left everything on the laptop when I went.

IT is quick to correct him.

IT obviously says, “Well, it doesn’t work like that. But do you know where (my name) stored it?” He, of course, had no clue.

So he sends me an email (to my private email address), attaches the administrator (who is responsible for several different groups), and says, “Well you two maybe could work this out?”

The employee is forced to get involved, once again.

I take my time and explain to him, once again, the computer is wiped (per IT’s protocol, the files are in the cloud, etc.).He responds with thank you, and then later I get an email that he sent to the new coworker (who I have never met), where I am CC’d, and says, “I attached (my name) in the thread, so that you can ask them if you run into issues.”

Once again, I was let off two months ago.

This man earns about 5x my salary.

Rude and incompetent. Pick a struggle!

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What did Reddit have to say?

If this employee is going to help, he may as well charge for it.

Screenshot 2026 07 13 at 5.55.55 PM A Defired IT Specialist Is Laughing After His Former Company Hit the Emergency Button

This user makes their stance crystal clear.

Screenshot 2026 07 13 at 5.57.09 PM A Defired IT Specialist Is Laughing After His Former Company Hit the Emergency Button

This reader shares what they would say.

Screenshot 2026 07 13 at 5.57.50 PM A Defired IT Specialist Is Laughing After His Former Company Hit the Emergency Button

No pay, no talk.

Screenshot 2026 07 13 at 5.58.42 PM A Defired IT Specialist Is Laughing After His Former Company Hit the Emergency Button

There’s a certain irony in a remote boss who ran the business almost entirely through email somehow forgetting how his own team’s file storage worked the moment it actually mattered.

This employee did everything correctly on his way out, and IT confirmed it immediately, yet the toxic boss still chose to drag a former employee back into the loop anyway rather than simply taking accountability.

Some people just weren’t meant to be in charge — and stories like this prove it.

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Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.