Use a Virtual Machine to Sync with an Old Pocket PC or Smartphone?

I tend to listen to the podcast version of Leo Laporte’s Tech Guy radio program when I want to listen to something interesting while driving but don’t want to pay attention to very single word (which I tend to do when listening to something like the Security Now podcast). I have a backlog of these files on my iPod. Today, I was listening to Show 363 from June 23 and noted the segment about someone who has an old Jornada Pocket PC who can’t sync with Windows Mobile Device Center (WMDC) on Windows Vista.

The issue is that WMDC only supports devices going back to Windows Mobile 2003. The last Jornada model was a 2002 device. So, you can’t sync it on a Vista PC. The caller seemed aware of the issue and asked if a Windows XP virtual machine running on Vista might be able to sync with the Jornada if ActiveSync was installed on the Windows XP Guest OS. Leo correctly suggested using either VMware Workstation or Parallels Desktop for Windows. However, the caller asked if Microsoft Virtual PC (which is free) might work too. Leo agreed. Alas, that is not the case. Microsoft Virtual PC has virtually (pun intended) no USB device support. So, it wouldn’t see a Pocket PC or Smartphone and partner it to ActiveSync. VMware Workstation and Parallels Desktop for Windows, on the other hand, have pretty decent USB device support and should be able to run ActiveSync in a Windows XP Guest OS and partner with an older Pocket PC or Smartphone. I haven’t tested this myself. So, you might want to verify this using a 30-day trial before plunking down your hard earned dollars. I have VMware Workstation 6 though. So, I’ll get around to testing this idea one of these days.

FYI: You aren’t limited to virtual machine running on Windows Vista. If you use a Mac, Parallels Desktop for Mac and VMware Fusion have good USB device support too. The wrinkle in this story is Apple is releasing a major upgrade (Mac OS X 10.5 Leopard) next week Friday. All this should still work under Leopard. But, it wouldn’t hurt to check first. I’ve got my upgrade copy pre-ordered and plan to install it next weekend.