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Many years ago I worked for a small company who’d just hired a new CEO - and the guy hated me for some reason. He used every chance to make inappropriate remarks, and at times he’d just get angry and start yelling at me because his MacBook wasn’t doing something the way he wanted it. Keeping in mind, I didn’t do support for endpoints, my specialty was servers and network. I’d just let him go off because he wasn’t local, and would only come to the office for a day about once a month.

One day he called into the office and asked for me (again there are other support people who could easily help him with his macbook issues). He states he’s on a train, and can’t send or receive e-mails. Assuming he’s done basic troubleshooting, and not wanting to piss him off further, I go through normal troubleshooting steps. After several minutes he gets angry again, and starts yelling at me, so did what anyone would do - I put him on speaker phone so everyone else in the office could hear his rant. We all had a good chuckle.

Once he’d gotten it out of his system, I suggested he give me his remote access info (we’d installed remote access software on his macbook for this very reason) so I could remote into his system and see for myself what was going on. He states the software won’t display the one-time access code…so I asked him if he was connected to the WiFi, there was a pause, and then and the phone went dead, he just hung up on me. Magically his email started working after that

I had a user ask us to solve her problems slower because it made her feel stupid when we solved them immediately.

“Can you tell me why my printer won’t print yellow?”

“Well first, it is a color printer? And there is yellow ink in it?”

“Oh, yes!”

“Can you print green?”

“Green works fine!”

“. . . That printer only has 3 colors of ink, if you’re printing green that means yellow is coming out…”

Tried uninstalling and re-installing printer drivers, changing cables, cleaning cycles, examining the print head, everything seemed to be fine…

“Oh, oh, oh! Should I be printing on WHITE paper?”

“. . . Are… are you printing on yellow paper?”

Me: Here’s the URL for the web service I’ve just deployed. I’ve set up users and permissions so just copy it into your browser and you should see a very similar system to what you’ve been trained on with all your data in there.

Customer: All I’m getting is a blank screen.

Much panicking and headscratching later…

Me: Waaaiiiiittt, did you press Return/Go after copying the URL?

Customer: That was not in the instructions.

I got a call from this woman in Boston, out was just a product activation call so I had to read her a 20-character activation string. We use the NATO Phonetic Alphabet for those, to reduce confusion over the phone.

The last character was Y-Yankee. I followed that up with “but I guess that’s a politically incorrect word around Boston, huh?” And she goes on an absolute tirade about how people are way to sensitive, throwing out a few racist dogwhistles along the way.

I just said “Ma’am, I was making a joke about the rivalry between the Boston Red Sox and the New York Yankees.”

She went silent for a few seconds and hung up on me.

I accidentally wiped a column in a police department’s evidence database 😁😅

This was way back but had a basic support call for someone who couldn’t get their mouse to work.

After speaking with them for over ten minutes and just being generally confused I cut to the chase and asked, “Ma’am, what are you doing with your mouse right now?”

The answer? She was moving the mouse around on the monitor.

Years ago I was working in a sales / support call center. One day in between calls someone posed the question of if you had to sleep with someone of the same sex who would it be. Obvuois answers were things like George Clooney Brad Pitt etc. one of our team was extremely introverted so it was normal for him not to participate.

3 weeks later he pipes up, “I’ve given this a lot of thought and If I had to sleep with a man it would be Jesus Christ” 3 weeks later. Blows my mind he was in deep contemplation for so long. I still am taken a bit back.

The reason? “Jesus seems like he’d be a considerate lover with strong hands.” Beautiful.

Had an older coworker who was on a long call with a user; his hands got tired so he put it on speaker after a while.

At a certain point my coworker fell asleep… and so did the user on the phone (snoring).

Half an hour of troubleshooting a user who said they couldn’t reach their file share on their network. They didn’t have access to the internet… They didn’t have access to anything else on the network… Switch under their desk indicated not connecting to the rest of the network. Asked if they would go to the server closet, they said they couldn’t, because an overzealous wrecking ball went through that closet this morning. Not even joking…it was to take down the neighboring building which was being knocked down for being a code violation for being too close to my client’s building.

When I worked help desk, a coworker of mine took a call where someone called in because one of the thin clients was on fire. The user was advised to call 911.

I was helping a user reset their password and the convo went something like this: Me: Ok, your temporary password is Password1. Log in with that and you’ll be prompted to change it. User: Is that a capital 1? Me: No, just a regular 1.

I got called in to handle a situation where an employee was spying on his boss’s emails. He got caught when a read notification went out from his account.

He got called into a meeting and when they explained what it was about he didn’t say a word, but left the meeting, went back to his office, removed the hard drive from his computer and left with it.

I just had to figure out what he’d done, make sure he didn’t have any further access, and fill in until they hired someone permanent. No idea what happened after that.

Before I was officially in tech support but I was the unofficial helper in my office. I don’t recall the exact issue this person was having on their desktop but I went over to help and said “have you tried restarting?” This person, a millennial, probably younger or the same age as me, then pressed the power button on the monitor to “restart”. I’m still reeling.

people that use their recycle bin as storage. there have been multiple. once I was at their desk, looked at their trashcan next to their desk and asked if it would be smart to store stuff in there. they got the point after that.

or the new user I setup, went to lunch, came back and needed his password reset because he forgot it already.