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Under Windows 7 I ran iTunes in XP Mode which was great. I plugged in my iPad (1st generation) and Windows XP picked it up and synced with iTunes.

Now I have upgraded to Windows 8, and I knew that Hyper-V would replace this functionality. I created a Windows 7 virtual machine with iTunes and enabled "Other supported plug and play (pnp) devices" in Remote Desktop.

If I plug in without iTunes installed, Windows 7 downloads the driver and I can read the iPad disk contents.

If I plug in with iTunes installed, I keep getting "Driver installation failed" error.

Does anyone know how how I can get the iPad working with the guest iTunes?

(Note: No, I do not want to install VirtualBox. The point of this exercise was to remove bloat from my system!)

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Why don't you just install iTunes on Windows 8? iTunes supports Windows 7, there isn't any reason, to run the application in compatibility mode. – Ramhound Oct 28 '12 at 12:43
That is correct, however I really dislike iTunes and would rather it was segregated. (The Windows XP mode in Windows 7 has served me very well in this respect) – Andrew Oct 29 '12 at 2:05
I don't understand the point of segregation. The resource usage would still be the same, in fact more since you're using a guest machine to run it. – KronoS Oct 29 '12 at 15:49
I run a lot of virtual servers on my laptop. Since these are often used for customer demonstrations, I have as little software installed on my host as possible. You are correct in saying that my scenario would use more resources, however for the most part that client virtual machine will be in a saved state and not running. – Andrew Oct 30 '12 at 3:02
+1 for quarantining iTunes. – Tanner Faulkner Nov 1 '12 at 15:21
up vote 1 down vote accepted

You can use this software for syncing ipad/ipod over the network or over the VM (supports Hyper-V):

USB Network Gate allows attaching a USB device to a guest OS running on Virtual Server. All you have to do is install USB Network Gate on host OS of any computer on your network and share a USB device there. Also install USB Network Gate on guest OS of any computer on your network, where you want to use the device, and connect to a shared one! USB Network Gate provides USB passthrough to guest OS running on Virtual Server. The OS will treat this USB device as a real one and you can work with it as if it were connected directly to your Virtual Machine. NetworkGate

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Thanks, that is a valid answer for a commercial option. However I was hoping to use the existing built in RDP USB functionality that 'should' work. – Andrew Nov 2 '12 at 2:08

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