It's always Computing 101 in tech support

There's no such thing as a dumb question? These three help desk cases may test that old adage

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But the first time he took the laptop home I received an email, sent via his smartphone, informing me that he was unable to connect to the VPN with the laptop. I called him and began to troubleshoot the issue over the phone. He became increasingly agitated about the "defective" laptop he'd been given.

Ignoring him as best I could, I kept troubleshooting. Eventually it became clear that he couldn't connect because he never joined the laptop to his home network. He assumed that by clicking on the VPN program, the laptop would connect to the Internet all on its own.

When I pointed out the problem, he tried to blame IT for not designing a better VPN program. I again bit my tongue, helped him connect to his own network and access the VPN -- and got off the phone as soon as I could.

At least there's a little satisfaction in witnessing a "pride goeth before a fall" moment, even if the person doesn't acknowledge it.

Road rules

Another executive who absolutely loved technology insisted on having an iPad rather than a laptop, since she didn't want to carry a heavy notebook. Enough higher-ups backed her request that the company provided her one in lieu of a laptop, though it wasn't a standard policy.

The iPad had a data plan, so there were no worries about connecting to the local network. It was also configured with VPN and remote desktop software to allow her to work while on the road. I spent two hours making certain she was familiar with the process to establish the VPN connection and to remotely access her desktop computer, including how the software allowed her to control the system back at the office.

For a while, everything seemed to be going smoothly. Then she went out of state to a national conference.

I received a phone call from her Sunday morning, saying the remote desktop app wasn't working. I walked her through all the steps to make sure she was doing everything correctly. She appeared to be on the right track, but the connection to the desktop failed every time.

In a flash of inspiration I asked, "Did you by any chance turn off your computer before you left?" She replied, "Of course. I am out of town for two weeks, so there was no need to waste energy."

I had to explain -- again -- that the remote computer connection worked only if the computer was turned on. Then because the presentation she was supposed to give the next morning was residing on her computer's hard drive and needed to be sent via email to the conference organizers by 5 p.m., I drove into work on Sunday to turn on the computer.

She was horrified that she made such a simple mistake and caused me extra work on the weekend. In fact, she bought me lunch to apologize for her error when she got back from the conference.

The apologies are appreciated, the surliness tolerated, and user misunderstandings numerous. That, of course, will never change -- no matter how much tech evolves.

Send your own IT tale of managing IT, personal bloopers, supporting users, or dealing with bureaucratic nonsense to If we publish it, we'll send you a $50 American Express gift cheque.

This story, "It's always Computing 101 in tech support," was originally published at Read more crazy-but-true stories in the anonymous Off the Record blog at For the latest business technology news, follow on Twitter.

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