Even when you have an upgrade available for your Windows Mobile phone, it may not be the most pleasant device upgrade you've ever done. In fact, it can be one of the worst. There is speculation that the WinMo 7 upgrade story will be vastly improved, but for now, we don't have that.First of all, when you upgrade, it is almost always like formatting your hard drive and starting over. You'll have to reinstall all of your apps, re-establish partnerships with your PC, reconfigure all of your preferences, like ring tones, SMS alerts and alarm sounds, and set up your email accounts again, including signatures and sorting preferences. If that is all you have to do, you are among the fortunate. Yes, there are some third party utilities that claim they can back up all of this information and then restore it after your upgrade is finished, but I've met with varying levels of success with this. As soon as you run into any glitch, you might as well hard reset your device and start over because you'll spend less time setting the device up than you would troubleshooting seemingly random glitches.

Some have to go to even greater lengths just to go through the above painful process. Walt Zwirko at Projo.com just upgraded his Samsung Jack to WinMo 6.5. Kudos to Samsung for offering the upgrade. Shame on Microsoft and Samsung though for making this a painful process. Walt used the MyPhone service to restore many of his documents and files, but that does nothing for settings.

Walt is using Windows 7 64bit on his machine. Guess what? The upgrade utility provided by Samsung won't work on any version of Windows 7. Come on Samsung! Windows 7 has been available to the general public through betas since January and the October launch date has been known for a long time. How can you not support the new OS? Those people just as enthusiastic about a new OS on their device are very likely to have the latest OS on their PC as well.

64bit versions of Windows have been out for years, but the upgrade also won't work on those. You have to have a 32bit version of XP or Vista. Ridiculous.

Apple has this whole thing nailed. Upgrades for the iPhone have thus far included all of the older models and when you upgrade, all user settings and files are preserved. Hopefully Windows Mobile 7 will mimic this model. Until then, be thankful if your device maker provides an upgrade for your WinMo device, then be prepared to spend several hours from start to finish. That is, unless you have to go roaming the neighborhood looking for someone with the right versions of XP or Vista that will let you use their PC to perform the upgrade on.