Some of my anecdotes
The year was 1996… we had two computers in the (primary) school library, both around 386 class. Both fitted with sound cards and CD-ROM drives. Both had 5¼ drives too.
One had a tray-loading CD-ROM drive. The other took a CD-ROM in a caddy. (And yes, I still have some of those caddies, and some SCSI Plextor CD-ROM drives that take them.)
When one student was confrunted with the caddie-loading CD-ROM machine, and a bare CD, how do you get the CD into the machine? Well, it fits in the floppy drive!
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The year was 2009. I was doing volunteer network administration for Asperger Services Australia who had appointed a new president. Supposedly from an IT firm. I was studying at uni at the time: Bachelor of IT (Software Engineering) / Bachelor of Engineering (Electronics: Telecommunications). My father was also involved with this group at a high level, he too has similar qualifications.
We were conferring with this person, I can't recall the full context, possibly something related to 3G networking or some such, but then he dropped a clanger:
President: I can't understand how these radio waves don't bump into eachother!
My father and I just looked at eachother flabbergasted! If we had told this bloke the truth (i.e. they do bump into eachother), it would have blown his mind!
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I was at a radio club meeting when one of the other members wanted to show off some digital slow-scan television software on his laptop. So he gets a laptop out, plugs it into power, grabs a mouse and plugs that in, turns the machine on.
Then wonders why his mouse isn't working. A quick look around the back, he "plugged" it into an Ethernet socket.
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At my present workplace, we were using WPA{,2}-Personal for the WIFI network. I wasn't happy about this, so I decided to duplicate the WPA{,2}-Enterprise system I use at home, but using an LDAP back-end for RADIUS.
After a bit of tinkering, I got it working, set things up. Now we have mostly Windows 7 machines here, and Microsoft likes making connections to WPA Enterprise difficult when the RADIUS' TLS key is produced from a self-signed certificate authority. Not a problem on Linux, MacOS X, iOS or Android, but Windows has always been a pain.
So I produced a short guide in our intranet Wiki site on how to connect one's Windows 7 laptop to the staff WIFI with the view that later, we would make our old WIFI network a guest WIFI with limited access. The link was emailed to all staff.
Managing Director: I tried connecting to the WIFI network. It didn't work.
Me: Did you try following the guide?
MD: No, I deleted that email.
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Same workplace, this happened recently to one of my colleages. We support a number of SCADA systems operated by various mining companies. They all like using these RSA SecurID tokens for their VPNs. These are a time-based token with a 3-year battery life.
Some tokens for one company's network expired. So we put a request in, and soon enough, new tokens arrived. So he tries to set up one of the tokens, then discovers he can't set the pin number.
So whilst on the phone to their helpdesk, they ask for his computer's hostname. They wanted to remote into his machine to deploy the software needed.
Now, I as network administrator, would love to know how they think they can, bold as brass, just stroll through our two firewalls into the machine in question when it can't connect to their network directly to install a piece of software.
Apparently they didn't have an installer file that they could just send us. It had to be deployed via their network tool, which presumably assumes the machine is joined to their domain, not ours.
It was pointed out that we were not employees of the mining company, the machines were not supplied by the mining company, and that we were external contractors brought on to provide technical support.
Next, they have us a procedure which involved entering a number into the token. Great. Except there's no keypad or interface to enter anything into this token.
I think the problem was eventually resolved.