iPod Nano 5th Gen - Want to restore to Windows iTunes via Parallels

[verena]

I have a 5th Gen iPod Nano. Works fine on my iMac. I want to use it on Windows via Parallels in order to put WMA audiobooks downloaded from the library on it.

So, I open Parallels, open iTunes in Windows, and attach the iPod via USB. I tell the Parallels popup that I want to use the iPod on Windows. Windows iTunes tells that I need to "restore" the iPod. Good enough. I click the restore button, wait for a bit, and get the following error:

Cannot restore or update in iTunes (1439)

I've tried this about 8 times. The iPod doesn't function after this happens. I then put it on the iMac, with Mac iTunes, and I get a message that it needs to be "restored" on the Mac iTunes, which I do, and then the iPod functions just fine.

I try to restore on iTunes on Windows again, and get the same error:

Cannot restore or update in iTunes (1439)

I must be missing a step somewhere. I've googled the problem to no avail.

[Jesse Hollington]

Make sure you've got both the latest version of Parallels and iTunes installed, and reinstall iTunes under Windows just to make sure the USB drivers are properly in place. Parallels' USB communication can be a bit off at times, and it sounds like this is where this error is coming from.

However, if your goal is to put WMA audiobooks on your iPod, you may be going to unnecessary effort anyway. The iPod will not support WMA files on any platform -- Windows or Mac. iTunes will support unprotected WMA files on Windows, but it converts them to AAC or MP3 files in the process of importing them. Therefore, you might as well just convert them yourself -- either using iTunes on Windows or any other WMA-to-MP3/AAC conversion tool, and then import them into your Mac iTunes library in the same way as any other file.

[kornchild2002]

XLD is a pretty good converter/ripper for OS X as well and it is free. I don't see a reason for going through Windows to sync something that can never be synced to the iPod anyway. Might as well just do the conversion in OS X and sync right away.

As for the errors, my guess is that something is happening when the iPod is put into its restoration mode. It is sending a "ready to restore" signal to your Mac but it sounds like OS X is interpreting it instead of Windows. I have a similar issue with an external optical drive of mine. When I am in Windows, I can insert a disc and instruct Parallels to load the disc into Windows XP instead of OS X. However, once I am done with the disc, the software I use automatically ejects it. I pop the disc back in and Windows cannot see it until I actually turn off the external DVD drive and turn it back on.

[verena]

Here is a screenprint of the library's description of the Overdrive WMA file:



It clearly lists iPod as a useable device for the file. In my past research, I read in a few places that the files will work on an iPod, but only if transferred from Overdrive to the iPod via iTunes for Windows. Thus, I am trying to do this.

I will reinstall iTunes for Windows tomorrow, and will report back if I have any success.

In the meantime, I have the file on my Zune HD. It works, but the controls on the Zune are a PITA.

[Jesse Hollington]

Ah yes, Overdrive. Unfortunately, that does mean you're probably stuck with loading it from Windows. Overdrive is the one weird exception to the rule regarding WMA files... Although the iPod does not support WMA files directly, Overdrive titles that are licensed for iPod use can be converted to AAC in order to be played on an iPod; however because the WMA files are in fact DRM-protected to begin with, this conversion can only be done in the Windows version of the Overdrive Media Console, and the tracks must be loaded directly onto the iPod in manual mode.

It's actually kind of a silly copy protection scheme, as you could just as easily copy the tracks back OFF the iPod and put them into your iTunes library as they're unprotected at that point, but obviously the goal is not to make it too easy to copy and/or keep the files

The Mac version of the Overdrive Media Console doesn't support WMA files for the same reason iTunes for Mac does not -- the necessary Microsoft support libraries for the WMA format are only included with the Windows operating system, and clearly neither Apple nor Overdrive sees any point in paying licensing fees to Microsoft to support a Windows Media format for Mac users

[verena]

I was finally able to get hold of my husband's work laptop tonight, and was able to restore the iPod on iTunes for Windows. It would appear that the issue was that the drive needed to be reformatted by Windows before the restore, and for some reason the version of Windows I am using on Parallels didn't/wouldn't/couldn't accomplish this step.

I was able to reformat the drive on the Windows laptop, and then restore the iPod on iTunes on Windows. I moved the iPod over to my iMac and synced it to iTunes for Windows on Parallels, and I was able to load the audiobook from Overdrive.

All is well.