Syncing iPod to iTunes in VMWare Windows Guest

[phillywize]

Hey all,

Any thoughts on syncing an iPod to iTunes running in a Windows VMWare guest? Anyone else doing it? How's it going?

I know there are many FOSS options out there, and Gutsy comes with support, but this is a situation when I just have to say I'm stuck on iTunes. I've made this arrangement work by using iTunes installed on a Windows running under VMWare server.

My main issue is coordinating USB handling between Gutsy and the VM. Gutsy recognizes and mounts the iPod...if I then mount the iPod under Windows (in VMware, VM>Removable Devices>USB Devices>Apple iPod), I get an unsafe ejection error from linux. What I've been doing is (duh) unmounting in linux, then mounting as above in the Windows VM, and it all works great...when it works.

Here are my outstanding issues:

- VMWare does not reliably recognize that my iPod is connected -- usually I have to leave it plugged in for a few minutes before VMWare discovers it and can make it available to Windows.

- This crazy back and forth arrangement appears to have corrupted my iPod on one occasion, necessitating a full restore. Of course, the iPod itself worked fine -- allowing full access to everything I had on it -- notwithstanding that iTuness thought it was corrupted. Also, linux could read the thing just fine.

- Occasionally, without actually] corrupting the iPod, windows will only recognize it as a corrupted iPod - but when I eject and reconnect it, it's all good (notwithstanding the one time it was really corrupted and required a restore).

Other than that, I think this is a good arrangement.

Here's what I've done to make it work:

- Kept my iTunes directory on my linux partition, shared with the VM by way of samba...much more comfortable than either (a) giving the VM access to a real drive (not a great option since I'd have to install an ext3 driver in windows anyway); or (b) sticking my music library into a virtual disk (yikes).

- I use firefly/mt-daapd to share my library from linux, rather than iTunes. A little more flexible. And it's kind of trippy to see my library as a share in iTunes.

- Other than that, not much.


Anyhow, anyone else doing it? How's it going? Happy to lend a hand where I can.

[phillywize]

Well, I know someone will eventually search for, and find this thread, so I'll post my progress to date:

(Please note, this is not a howto! For starters, I don't know what I'm doing or why it works. This is all basically the epistemological equivalent of sorcery. So I can't really tell you how to do it...but if you're having similar problems, or know a sure solution, please, let's do talk. In the meantime, this is what's working, more or less, for me.)

I've had some reliability problems with syncing since my last post. At one point I couldn't get iTunes in my Windows guest to recognize my iPod properly -- no matter what I did, it told me that it detected a corrupt iPod that would have to be restored (i.e., blanked and then everything loaded back onto it).

Unwisely, I went for this time consuming operation. It worked, but then the next time I went to sync, the same thing happened (iTunes: "you have a corrupt iPod, etc."). This time I didn't do the restore...instead I did some more monkeying. Here's what has worked most reliably (although not flawlessly) for me:

- With Windows running in VM, connect my iPod with the USB cable. The Ubuntu host recognizes and mounts the iPod.

- If I immediately check under VM>Removable Devices>USB Devices>Apple iPod, there's no iPod...yet. I wait a few minutes, and usually it shows up there. It has no check mark next to it, which, I divine, means that the potential iPod USB connection is known to VMWare, but the connection is not made yet. So as not to make further trouble for myself (by damaging the iPod file system), I eject it from the Ubuntu host.

- Miraculously, it remains known to VMWare.

- I then select the iPod in VM>Removable Devices>USB Devices>Apple iPod. Windows then recognizes and mounts the iPod.

- I start iTunes, which, after some cogitation, recognizes and syncs my iPod. This process also seems to work with iTunes already running. I don't think it's the most delicate aspect of it.

When I've tried to let select the option in iTunes to make the iPod available in windows as a drive, it generally causes trouble: iTunes unmounts and remounts the iPod to effect the change, but when it's remounted, iTunes thinks it's corrupted (which it isn't).

Anyhow, we'll see how this goes. I'll keep talking to myself here in hopes that it will start a helpful dialog, or otherwise be useful. But remember, I don't know what I'm doing.

[flaggh]

I have been trying for months to get my iPod to sync through iTunes in a virtual guest XP install. I have used exactly the same steps as you and can only get as far as having XP detect a removable storage device. The VMware menu lists Apple iPod under USB devices but XP does not properly detect the iPod. I've tried using both VMware server and Virtualbox with no success on either one. I have not tried the new VMware server beta, is that the one you are using?

My computer is an older laptop that only has USB 1.1 ports. I never had any problems syncing my iPod when XP was the base OS. I've synced using banshee and gtkpod but would still prefer using iTunes. I've even tried RockBox but quickly removed that after it kept freezing up on me.

I believe my older laptop hardware is to blame for my syncing problems in VMs, but I cannot think of any way to confirm this.

[phillywize]

I have been trying for months to get my iPod to sync through iTunes in a virtual guest XP install. I have used exactly the same steps as you and can only get as far as having XP detect a removable storage device. The VMware menu lists Apple iPod under USB devices but XP does not properly detect the iPod. I've tried using both VMware server and Virtualbox with no success on either one. I have not tried the new VMware server beta, is that the one you are using?

My computer is an older laptop that only has USB 1.1 ports. I never had any problems syncing my iPod when XP was the base OS. I've synced using banshee and gtkpod but would still prefer using iTunes. I've even tried RockBox but quickly removed that after it kept freezing up on me.

I believe my older laptop hardware is to blame for my syncing problems in VMs, but I cannot think of any way to confirm this.

I'm using VMWare Server 1.0.3, and have not tried the beta. I would think that if anything, the USB 1.1 would be an advantage inasmuch as it's more basic (and ubiquitous). But I could be wrong about that.

Have you tried syncing with iTunes running already?

Also, have you tried ejecting your ipod from XP? I've noticed that when I eject, windows itself recognizes that there's an iPod in the set of devices being deactivated. That might be helpful on the off chance that your problem is more with windows than with the vm.

Sorry not to be of more help! I'm the paradigmatic ubuntu user. Tech savvy, willing to mess around, but at the end of the day, not terribly knowledgeable in the finer points of linux.

[phillywize]

I have been trying for months to get my iPod to sync through iTunes in a virtual guest XP install. I have used exactly the same steps as you and can only get as far as having XP detect a removable storage device. The VMware menu lists Apple iPod under USB devices but XP does not properly detect the iPod.

You know, here's another thing that has worked for me: after you have windows recognize that you have something plugged into a USB port -- and I assume at this point, "Apple iPod" is recognized and checked off in VMWare, eject from within Windows, leaving the VMWare setting alone (don't uncheck "Apple iPod"). Disconnect the iPod, and plug it back in.

I know, you've been at this a long time, so you probably tried it already, but just in case. I have noticed that sometimes Windows recognizes my iPod as corrupt the first time around, but if I do the above once or twice, it finally gets it.

[flaggh]

Thanks for taking the time to think about this and offer suggestions. My experiments trying to get this to work have not always been so methodical so I've lost track of the exact conditions I've used in the past. I will definitely give these a try next chance I get and report back.

[casposa]

that's a great workaround! it works! yes....I'm finally going to kick out my windows partition...(as a have a classic ipod...native linux libraries and programs don't work yet...)

[phillywize]

that's a great workaround! it works! yes....I'm finally going to kick out my windows partition...(as a have a classic ipod...native linux libraries and programs don't work yet...)

Glad it worked...what problems were you having (detecting as corrupt, etc.), and what worked? I think it will be helpful for future readers to document what does and doesn't work.

I have been enjoying continuing success with the approach I set out. As long as I follow the rules, the system seems pretty robust.

One thing I haven't been able to do is sync photos -- that somehow triggers redetection of the iPod as corrupt when I try to sync photos (iTunes actually sees two iPods, though only one is plugged in: the actual iPod, and the "phantom" corrupt one).

Anyhow, it would be nice to have a fix, rather than this odd semi-workaround.

[flaggh]

I've tried the methods you've suggested and still no luck with my VMware guest XP installation recognizing my iPod. Thanks for the ideas anyway!

[phillywize]

I've tried the methods you've suggested and still no luck with my VMware guest XP installation recognizing my iPod. Thanks for the ideas anyway!

Yeah, I just tried an XP VM with my iPod, and following the steps I set out above for doing it with W2k, and no luck. Something's different about XP.