Apple Wi-Fi Sync (iOS5) at home with VMware vSphere 5.0 (ESXi)

There’s a bunch of features I’ve really liked in iOS5, particuarly Wi-Fi Sync.     Since I wanted to centralise my music to my home server running VMware vSphere 5 (and a bunch of VMs),  I thought I’d also run iTunes inside my File Server VM (running Win2K8 R2).   My File Server VM could then tick away with iTunes running and download the latest podcasts each day.. nice !

My File Server VM automatically logs on when it starts.  I decided to do this for iTunes, but also apps such as Dropbox (which worked ok for a service for a while until it needed an update) and also FingerPrint.

OK, so I plugged in my iPhone into one of my home server’s USB 2.0 ports.  Within vCenter, I configured my VM and added a USB controller and then a USB device.  vSphere automatically detected the iPhone!  Yay!

With the latest iTunes installed, on the Summary tab scroll down and select the following:

I then ran a Sync on iTunes and when it’s completed,  I downloaded another bunch of podcasts on iTunes (something new for it to download).  I then plugged  iPhone and plugged it into another power source at home.   My iPhone then talked back to my iTunes (running on a VM on vSphere) and started sync’ing, just as I wanted!   See here:

My iPhone is now completely cable free, and the latest iOS 5.0.1 update (also cable free) worked flawlessly for me as well.   It will be interesting to see what the iTunes Match feature is like too, which doesn’t seem too far away.


To allow iTunes to automatically start without an error due “No Audio Device”    I needed to complete the following within my Win2K8 R2 File server VM, thanks to the following website:

1) Firstly run tsconfig.msc, click RD Session Host Configuration.

2) Under “connections” right click RDP-Tcp, under Properties choose “Client settings” tab  and uncheck “Audio and video playback”.

Then, I followed the instructions here about connecting to the VM with Audio remapped from my Remote Desktop Connection app and installed Virtual Audio Cable.   iTunes would then start without error.



  1. Hi Darryl, thanks for the post. Are you using Vmware ESXi with a wireless card? I’m wondering which wireless NIC I could use for my project..

      1. I moved it to Ubuntu (as Time Machine Backup) + Virtualbox (Windows Server 2003 with iTunes) now, running on an old Macbook which has built in WiFi..

  2. Hey there,
    I stumbled upon your site. I basically have the same setup, except having iTunes installed on a Windows 7 VM. When I startup iTunes in the VM, it recognizes my iPod Touch and synchronizes it over WLAN. So far so good. The problem now is that it generally only works this one time. When i plug it in a power adapter in the evening again to sync over night, it won’t work and I see the same error message about iTunes not being able to connect to the iPod Touch like 20 times. When i close and restart iTunes it works flawlessly, but I have the same problem the day after. Did you ever experience similar problems?

    1. Hi David,

      It’s working ok with me, although I must admit I’ve now started using Instacast and find it easier to listen to podcasts that way now !


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