Upgrading From Windows XP Is Not For The Faint Of Heart

As I write this column, I can see the flicker of the drive light on an HP workstation out of the corner of my eye. It’s flickering as the computer downloads and installs around 450 Windows updates, and as bad as that may seem, in reality, it’s the good news. The bad news is the process that came before, when I tried to upgrade the machine from Windows XP to Windows 7.

The bad news

I started this process on New Year’s Day. But here it is, many hours into another day and the task is only nearly complete. Why, you might ask, was I installing operating systems on a holiday? Well, I live in the Washington, D.C. area, and our local football team has managed to lose more games than it played this year. So there was nothing to watch on television.

I stumbled across an old Hewlett-Packard xw8200 in the lab that needed repurposing. But in the meantime, it occurred to me that this was a perfect opportunity to do the XP to 7 transition, since the machine wasn’t doing anything useful anyway. So I grabbed the original set of CDs from the file and slid the HP restore disk, followed by the Windows XP Professional disk into the drive as required. The installation ran perfectly, and in an hour or so, the computer was bright, shiny, and totally up to date, assuming that you live in 2005.

The next step was to run Windows Update so once I’d passed through the required hoops, I could then upgrade to Windows 7. But alas, it was not to be. Windows Update failed.

The good news was that the website that shows up when Windows Update fails suggests asking for help either in an online chat or via a phone call. It assuages worry by telling you that your tech support call will be free, since the problem is Windows Update. I remembered that in the past I’d called for help when Windows Update failed to work, and that the support was friendly and free. So I wasn’t worried.

Obviously, I’m easily misled. Windows Update support, at this point, isn’t free when it’s for XP. You can have paid support or nothing, despite the clear promise on the Microsoft Update Website. To make matters worse, there’s no good means of handling the updates manually, despite spending hours trying. Calls to Hewlett-Packard were referred to Microsoft, and calls to Microsoft were referred to HP.

Fortunately, there is a solution to all of this frustration, although it’s not obvious. I recalled what I’d learned when I’d installed Windows 7 the first time. Direct upgrades from XP to 7 aren’t possible. You have to do a clean install.

This is how we do it

Of course, there’s another option. I could use PCMover Pro from Laplink, which would let me move directly from XP to Windows 7 or 8 while keeping my files and applications. But for many businesses, the most obvious way to move from Windows XP to something newer is simply to copy the install files to a server and to try to run the upgrade.

That method won’t work. In fact, it appears to be impossible to do an upgrade if you want to keep your programs and files.

Yes, you can create a standard image of your client workstation and simply move that to the machines that must be upgraded beyond XP. But many smaller businesses lack the expertise. What they know is an upgrade that involves a PC. That, in turn, says it needs XP to be at Service Pack 3, which you can’t get very easily, if at all, these days.

After a few hours of failed attempts to get an elusive service pack, combined with calls to Microsoft support and demands of money, it’s no surprise that many business owners start contemplating computers without updates, or perhaps a move to Linux, which doesn’t get involved in such foolishness.

However, for many companies, the move to Linux and its accompanying learning curve are too much. So they believe they’re stuck with no upgrade path, no help and a computer that won’t be supported in a few weeks. What to do?

First, stop trying to directly upgrade XP to Windows 7 or 8. It won’t work. Use PCMover Pro for a couple of machines or the Enterprise version if you have more. Otherwise, if your data is backed up and you have only a few applications, then just blow XP away, install a clean version of Windows and restore from your backups.

A Microsoft spokesperson provided a step-by-step upgrade link here along with its official pitch on why all this is necessary. “Windows XP and Office 2003 were great software releases more than a decade ago, but technology has evolved along with the needs and expectations of your customers and partners that have already adopted modern platforms and devices,” the spokesperson said.

“Companies still on Windows XP are also missing out on tangible benefits of modernizing their IT investments from dramatically enhanced security, broad device choice to meet the needs of a mobile work force, higher user productivity, and lower total cost of ownership by future-proofing their IT investments. A 12-year-old operating system can no longer address today’s business and technology needs nor security threats,” he continued.

Unfortunately, the spokesperson didn’t explain why the upgrade from XP to newer operating systems isn’t as intuitive as it could be.

Alternative you can take advantage of the capitalization rules while you can still use them and write off the old computers. Then, install new Windows 7 or 8 machines before restoring your applications from backups. Then, get a modest tax break from donating the old machines.

Regardless, you’ll have to deal with the fact that Microsoft has made the necessary move from XP much harder than it needs to be because you have taken so long to upgrade to a newer version of Windows. Just bite the bullet and find another way to go.

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Originally published on eWeek.