Astute Windows users have pointed out the Achilles Heel of Microsoft's plea for help in getting customers to dump Windows XP: The lack of a smooth upgrade path to Microsoft's newest operating system, Windows 8.1.

"Wait. Wait. Wait just a minute here," wrote someone identified as "nephilim" in a comment added Thursday to a Microsoft blog. "You are suggesting I upgrade people from XP to Windows 8.x? But that's impossible. There is a major problem with [Microsoft's] suggestion. You (Microsoft) have made Windows 8 and 8.1 incapable of upgrading from Windows XP. I simply can't upgrade anyone, including myself, to Windows 8. It's impossible."

Nephilim was reacting to a Feb. 7 pitch by Microsoft that asked its technically-adroit customers to help friends and family still running Windows XP ditch the OS in favor of Windows 8.1. Microsoft will deliver the last public patches for the XP on April 8, after which users will be on their own, and -- as security professionals have pointed out -- in the crosshairs of cyber criminals.

"We need your help spreading the word to ensure people are safe and secure on modern up-to-date PCs," wrote Brandon LeBlanc, a Microsoft marketing communications manager, in a blog post two weeks ago. LeBlanc asked his readers to assist others in either upgrading their current Windows XP PC to Windows 8.1 or help them pick out a new machine to replace their aged system.

The problem with the upgrade option, as nephilim and others noted, is that there's no way to transform a PC running XP into one running Windows 8.1 without hours spent reinstalling applications and restoring files from a back-up.

In fact, before the official launch of Windows 8.1, LeBlanc warned users not to even try an XP-to-Windows 8.1 upgrade.

"Windows 8.1 is not designed for installation on devices running Windows XP or Windows Vista," LeBlanc said last September. LeBlanc also said the new update is "not recommended" for hardware now running Windows XP or Vista.

Users of XP can upgrade first to Windows 8 -- keeping data files, such as documents and photos, intact -- and after that grab the free Windows 8.1 update. (Microsoft has also said it is possible to upgrade straight from XP to Windows 8.1 with a "clean" install that retains nothing because it involves wiping the hard drive.)

A more thorough upgrade for Windows XP users is possible to Windows 7, a migration that preserves files and settings, but still requires the user to reinstall all the Windows applications they were running.

Windows 7 has its own issues, though. Microsoft pulled Windows 7 from its stores and stopped selling it to other retailers last October. However, most sellers have stocked up on Windows 7, and continue to move the 2009 OS at prices between $90 and $100.

But the contradiction in LeBlanc's appeal -- he asked customers to upgrade to Windows 8.1 knowing that there was no migration path from XP -- stuck in users' craws.

"It takes a lot to transfer an XP machine to a modern Windows OS, it is not automatic and it takes a LOT of time and some resources (external hard drive) and skills which the average user neither has, needs, or wants," said William Rushing on Friday in another comment to LeBlanc's blog. "If Microsoft is sincerely interested in getting the XP user base off of XP, they're going to have to write a direct upgrade tool that even the most technically illiterate person can use."

That's not going to happen.

There are third-party utilities that make an XP-to-Windows 7 or XP-to-Windows 8 migration easier by moving files, settings and even some applications. Laplink Software's PCmover program is probably the best known transfer and migration utility. LapLink sells a pair of versions -- Windows 7 Upgrade Assistant and Windows 8 Upgrade Assistant -- for $29.95 each.

But even with that kind of help, many of the people LeBlanc had hoped would pitch in simply won't. Among that group: Rushing.

"Thanks to the vagaries of modern life, I have nine -- count 'em, nine -- parents/in-laws," Rushing wrote in his extended comment on LeBlanc's blog. "They are all 70 years old with two exceptions. One is a programmer. I don't worry about him. The others are all still running XP machines. If I don't convert them, they are not getting converted. And I'm not: I don't have the time. Simply do not."

Gregg Keizer covers Microsoft, security issues, Apple, Web browsers and general technology breaking news for Computerworld. Follow Gregg on Twitter at @gkeizer, on Google+ or subscribe to Gregg's RSS feed . His email address is gkeizer@computerworld.com.

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