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True IT blooper #49: I told you so...

What's even more frustrating than the odd upgrade goof, is the goofy individual who refuses to accept what someone else has already learned the hard way.

The implementation of a new operating system invariably comes with a few hiccups. But migration headaches are necessary evils -- companies who refuse to stay abreast of newer technologies are doomed to join the ranks of the obsolete, eventually.

What's even more frustrating than the odd upgrade goof, is the goofy individual who refuses to accept what someone else has already learned the hard way.

A Windows NT system admin, our friend Gary thought moving his wife's small office from NT to Windows 2000 would be an easy job.

As part of his planned migration, he set about introducing a new Windows 2000 server into the office environment. He assumed that 2000 would handle an IP address change the same way that NT had for him in the past. But as you know, "when you assume, you make an a…" We'll let Gary explain:

"Changing a server's IP address isn't something that occurs on a regular basis and usually only happens when you set up a new one or have to change the IP for some other 'good' reason." As Gary found out, however, the execution of seemingly simple tasks can vary greatly from an older operating system to a new one. "Some of the old safeguards just don't exist anymore, " Gary explained.

Gary thought that he'd have no problem quickly re-configuring the box in question to be set up as a new Internet server. He changed one of the two NIC cards' addresses to be consistent with the firewall configuration that already existed. At the time, the server was acting as the domain controller, Web server and data server for the in-store ordering process.

Realizing that restarting the servers was not something he could get away with during regular business hours without losing customers, he planned to wait until all employees left for the night.

But the end of the day was a few hours away yet. The consummate professional, Gary was reluctant to simply sit on his hands and wait until the office was empty. "I thought I could get things set up on the server by configuring the NIC card ahead of time." It certainly sounded like a plan. Then, when everyone went home, he would simply select 'OK' on the Windows screen that prompts you to restart the computer so the changes can take effect.

Gary had always been a fan of the Windows required restart prompt. After all, it ensures that a user can't restart a critical system without just provocation and ample warning. With the prompt ready to be activated, all he'd have to do is some testing to make sure that he could reach the new server from outside the firewall. He'd ramp everything up while the office was still open for business, and then restart it all that evening.

That's when his first lesson in the differences between NT and Windows 2000 began.

At about 2:30 p.m. -- smack dab in the middle of the busiest ordering period of the day -- Gary changed the IP address on the Web side of the machine and waited for the prompt to come back to ensure that everything was ready to go. That's when five angry order-takers showed up wanting to know what happened and why they had all gotten kicked off the network.

You see, Windows 2000 server doesn't require a reboot to change the IP address; it just goes ahead and does it. Warns Gary, "It also resets all connections to the server at the same time -- regardless of whether or not you are changing the IP address on a NIC card other than the one users access the server on."

After some quick troubleshooting, Gary had the disgruntled employees back at their stations. "I definitely learned that old habits can get you into trouble when you're no longer in the same old comfortable environment," said Gary.

But wait, it gets better.

Later that week, a support tech from a local service provider came out to help with an unrelated network issue and told Gary that he wanted to change the IP address on the server. "I told him about the non-restart issue, and that the process would kick all of the users off of the system, but he assured me that I must have done something other than simply changing the address."

Gary pleaded with him to first get all of the users off the system, but the stubborn new arrival insisted. Two minutes later the same five users who had descended on his desk before were back -- and none too happy.

We're sure Gary was only too happy to say, "I told you so."

Share your bloopers with us. E-mail them to Read more of our past IT Blooper Series, which originially appeared at, part of the TechTarget network.

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