If you are still running XP on your desktop, like me, you may be thinking about upgrading to Windows 7. XP is getting long in the tooth, many newer programs (especially those from Microsoft) aren’t easy to run on it without a lot of effort, and you can’t upgrade Internet Explorer if you are interested in sticking with Microsoft for your Web browsing.

Of course, you may just want to stick with XP until your aging PC emits its last dying gasp and then just buy a new PC with Win7 already on it. That can be fine for some people.

But if you do want to upgrade, Microsoft doesn’t make it easy. The only way you can install Windows 7 is to wipe your disk clean and start with a fresh install. While this is appealing in a spring-cleaning sort of way, it may not be what you want to do. What they call an “in-place upgrade” – meaning that you can preserve your files, your applications, and your other customized settings – will only work if you are upgrading from Vista.

I have tested six different products that enable this migration directly from XP to Win7, and each has its good and bad points. Which product will work for you depend on a few different factors. Two of them are ideal for single PCs, or maybe up to ten individual PCs, but not for bulk migrations if you are planning on doing this across your entire corporation. These are Zinstall ($89) and Laplink’s PCmover ($20 to $60). I was initially attracted to Zinstall because it offers a very elegant solution: you create an XP virtual machine that can be summoned at the push of a button while running Win7 on your desktop. Inside this VM, you can add new apps or do anything that you would do with your regular XP PC. The only problem is that instead of running two operating systems I ended up running a useless piece of metal with no operating systems, because of something that was wrong with Zinstall’s install. Laplink’s software converts things as you would expect, so you can’t go back to XP once you have done the upgrade.

The other four tools are Microsoft’s Windows Automated Installation Kit (free), the Dell/Kace Kbox 2100 hardware appliance ($4500 for 100 PCs), Viewfinity User Migration (free while in beta), and Prowess’ SmartDeploy ($2000 per enterprise-wide license). Each of them has similar processes, because you aren’t really keeping XP around, just the hardware it is running on. The trick is preserving enough of your user’s footprints to make it feel like home. They work as follows:

• The tools start out with a fresh copy of Windows 7 as a master image.
• The entire machine is reimaged with Windows 7 — just without you having to sit in front of it while the bits are put on the machine from a standard install DVD.
• Next, they stir in the particular applications that you want to deploy across your enterprise. This gives you the opportunity to clean house and create a more managed environment, which may not be what your end users want to hear, but gets back to that spring cleaning sentiment mentioned earlier.
• Each tool has ways to deal with the variety of hardware configurations that you place the image onto, and some make it easier to copy the user application settings and data files over to the new world of Windows 7.
• Finally, you send forth the image to your desktops and have them reboot with the new copy of Windows 7.

Sounds complicated? Yes, it is harder than jamming a DVD into your drive and letting it do its thing for an hour or so. But if you get the tool working properly, you can do a massive upgrade in a matter of a few hours, no matter how many PCs you need to touch.

What do I recommend if you have dozens of PCs to upgrade? I would start with either SmartDeploy or the Kbox. Both handle things somewhat differently, and you are going to want to read and watch my reviews to understand some of the issues.

If you are in Chicago next Thursday evening May 20th, you are welcome to come by the Chicago Windows User Group meeting where I will be speaking about this topic and showing how to use each product in a little more detail. Email me privately if you would like to meet up.

If you want to read more, go to a page where I have links to the various articles and video reviews that I have done for sites such as ITexpertVoice.com, SearchEnterpriseDesktop.com and CIOupdate.com. You can go to links on each of the reviews on all six products here.

Don’t worry, the videos are just a couple of minutes long. Good luck with your own migration.