Why IT Pros Need Social Engineering Training (and a Stronger Coffee): A Tech Support Tale of Lost Files, Clueless Requests, and Endless Exasperation
It’s 8:17 a.m. The coffee’s just started brewing. You’re hoping for a quiet start, maybe some minor printer drama or a forgotten password. Instead, you’re greeted by an email that reads like a riddle, delivered with the urgency of a nuclear launch code: “Please write C/users/USERNAME and .../USERNAME/Documents to a DVD or USB for the external employee who’s now rehired under a new name.”
Welcome to the world of tech support, where the only thing more reliable than Monday’s chaos is the creative confusion of end users. As u/Adamantine-Waffle shared on Reddit’s r/TalesFromTechSupport, sometimes your job isn’t just troubleshooting technology—it’s deciphering human logic, policy, and the occasional fever dream disguised as a work request.
The Request: A Recipe for Exasperation
Let’s break it down. The task seemed simple: copy some folders from a user account to a physical medium. But, as any seasoned IT pro knows, nothing is ever that simple. The request was riddled with more holes than Swiss cheese:
- The data in question? Stored locally, not on the company’s OneDrive or server—meaning it wasn’t backed up, wasn’t secure, and definitely wasn’t easy to retrieve.
- The folders? Allegedly vital to the team’s function, yet stashed away on a personal drive, putting business continuity at the mercy of a single laptop’s lifespan.
- Identifying the machine? Good luck! No computer name, no device in sight, and with ex-employees, machines often get wiped faster than you can say, “Did you try turning it off and on again?”
- The method? “Write it to DVD or USB.” No media provided, and in 2024, who even has a DVD drive anymore?
- Security? The user likely had no permissions to read from external devices, making the whole exercise a bureaucratic dead end.
As one commenter, u/Salavora_M, so eloquently put it: “How the hell are you supposed to do that without the PC/Laptop?” Adding salt to the wound, they pointed out the risk of social engineering: “What guarantees do you have, that this truly is the same external person and not just someone saying that they are?” (A valid question, given the annual parade of phishing awareness trainings most IT staff endure.)
End Users: The True Source of IT Job Security
The real comedy here isn’t in the technical hurdles; it’s in the recurring theme every tech support veteran knows by heart: end users trying to dictate the “how,” rather than simply stating the “what.”
As u/Geminii27 observed, “It’s the annoyance of people telling you specifically what they think they need you to do, rather than asking for an end result and letting you handle it according to corporate policy and available resources.” This brand of micromanagement isn’t just inefficient—it’s a fast track to chaos, lost data, and (for IT) existential despair.
And let’s not forget the “quasi know-it-all users,” as u/igramigru101 calls them—those who wield just enough technical knowledge to be dangerous, sometimes with a dash of managerial authority. The result? Requests that break every best practice, delivered with the certainty of Moses descending from the mountain.
Policies? What Policies?
Corporate IT policies exist for a reason. In theory, when employees leave (or are “fired and rehired” under mysterious circumstances), their data should be funneled to the right manager, archived securely, and restored if truly vital. In practice? “Think they do it properly? Of course not,” sighs u/P5ychokilla. Instead, managers invent their own processes, then get “pissy” when tech support refuses to play along.
Even the original poster, u/Adamantine-Waffle, admits that the responsibility for verifying the right files and permissions fell elsewhere—and good thing, too. “Although I do wonder how the person who's responsibility it was, checked if the files are actually fine to write (and possibly take outside the company), considering I know for a fact that he also can't access others' drives.”
The cherry on top? After all the drama, the user kept the same laptop, so the files were just copied from the local cache. The IT equivalent of pulling a sword from the stone, but only after everyone’s spent a week searching for Excalibur in the lost and found.
Lessons Learned (or Not)
What’s the moral of the story? As u/henke37 notes, this whole mess could be avoided by configuring user profile directories to roam—putting documents on the server where they belong, not on a single vulnerable device. u/wanderinggoat adds, “They said they had OneDrive, so I would assume they use it for their profile”—the textbook definition of “optimism in IT.”
But as u/Rusty_M laments, “At least when they log complaints about their data being lost, management back us up as it shouldn't have been there.” Policies are only as good as the people who follow them—and the tech staff who have to clean up when they don’t.
And let’s not forget the truly vital requests, like the user who wanted their Teams chat history transplanted, because, you know, that’s where all the important company knowledge lives. (As u/Jonathan_the_Nerd quips, “No, I never wrote it down anywhere else. Why would I need to?”)
Conclusion: IT Pros, We Salute You
So next time you grumble about a slow printer, spare a thought for your local IT team. For every password reset, they’re handling a dozen requests that make the laws of logic weep and the company handbook curl at the edges. If you’re in tech support, take heart: you’re not alone. And if you’re not? Maybe ask for the “what,” not the “how”—and please, back up your files.
Got your own tales of tech support terror or wisdom? Leave a comment below—just don’t ask us to burn it to DVD.
Original Reddit Post: No better way to start the day than with a large dose of exasperation at user cluelessness.