Tech reasons not to upgrade to XP

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Pop-up messages
Windows XP displays pop-up messages indicating various system conditions. For example, you might see a pop-up message if a wireless network connection is out of range, if your display isn't running at a high enough resolution, or if Windows doesn't like the number of icons on your desktop. Some of the pop-up messages are for minor problems; others relate to more serious conditions. I certainly have no problem with system messages, but Windows XP seems to generate an excessive number of unnecessary messages. To an experienced user, these messages tend to be a minor annoyance. To the help desk, these messages tend to be a royal pain because they mean lots of unnecessary phone calls from less experienced users. File registration issues
Windows XP is less flexible with its file extension registrations than previous versions of Windows. For example, I have a video capture and editing package that I use extensively. When running Windows 98, I could double-click on an MPEG file or an AVI file, and Windows would open my personal video application. In Windows XP, clicking on a video file opens Windows Movie Maker, regardless of how many times I've reinstalled my video application. It's possible to reassociate file extensions by editing the registry, but doing so can be a pain, especially on a large scale. If your organisation uses obscure applications to work with common file types, your users may become frustrated with the way Windows opens the "wrong application." Patches and fixes
As in any other version of Windows, patches and fixes should be installed to keep Windows XP working correctly. You can bet on many more patches in the future. Windows 9x and Windows 2000 also have a lot of necessary patches, but if everyone is already running an older version of Windows, the more critical patches are probably already in place. Upgrading to a new version of Windows means downloading more patches and distributing them to all of the workstations. Tough-to-find drivers
It can be tough to find drivers for your older hardware devices with Windows XP--especially for hardware devices whose manufacturers have gone out of business or have quit supporting the particular device in favor of a newer model. Even if you do manage to find a working driver, Windows will try to discourage you from using any device driver that hasn't been digitally signed by warning you about the consequences of accepting unsigned drivers with several pop-up dialog boxes. When a hardware device doesn't have a device driver available, you might be able to use a Windows 9x, Windows 2000, or even Windows NT driver in its place. Still, if you don't have a Windows XP driver available, it's hard to know which, if any, of the other available drivers will work. Often, it comes down to a time-consuming process of elimination. Real technology needs
Some would argue that an upgrade would be worthwhile because of bug fixes and security enhancements, but if everything is already working properly, bug fixes aren't really a consideration. Likewise, if you operate in a low security environment, security enhancements probably won't be a big selling point. Your IT manager should carefully consider the company's technology needs for the next several years. Even if he or she gave you a large budget for an upgrade and all of your systems are able to handle Windows XP, you may simply not need it to stay competitive. Some organisations can get by on older operating systems for several years after they're considered past their prime. Unless your company must stay on the cutting edge to keep up with its competitors, you can save yourself a lot of headaches by avoiding the time and expense of an unnecessary upgrade. User training
Training is expensive, and users must spend time away from their normal duties to acquaint themselves with the new operating system. Otherwise, support calls will mount up and you'll spend a good deal of your admin time answering basic OS questions. Windows XP has a different (some would say better) user interface than Windows 9x, Windows NT, and Windows 2000. Although the interface is fairly intuitive, rest assured that unless you provide adequate training, some users will have a difficult time figuring out the new interface.
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