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I'm running iTunes 11 on my Mac with an old iPod touch (iOS 5) serving as a jukebox and an iPhone 4 (iOS 6.1) as my main device. Both are set up for wireless synching.

When I start iTunes, it finds the iPod and synchs with it wirelessly without trouble, but it doesn't find the iPhone, forcing me to connect it to synch with the dock cable.

If I disable wireless synching for the iPhone in iTunes, synch, re-enable wireless synching and synch again, wireless synching returns and works again.

Until such time as I quit iTunes and restart it.

Why does this keep happening? It can't be a network/firewall problem, because the iPod keeps on synching with the same machine through the same network. Needless to say I'm finding this pretty frustrating, what's the point of wireless synch if you keep having to re-enable it with the dock cable every time you start iTunes?

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  • I'd a lot of problems with Wi-Fi sync before. I totally understand you. Anyway, have you tried restarting your network. Or resetting your iPhone's network settings.
    – Can Sürmeli
    Commented Feb 14, 2013 at 19:39
  • It seems to be spontaneously working again without any changes at all. Of course I could lose wifi sync again any minute so I'm not counting the problem as resolved yet until I know how to make it work reliably.
    – GordonM
    Commented Feb 14, 2013 at 20:16

3 Answers 3

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I've been investigating this problem for a number of years now and I've concluded the following:

  1. Most home wireless/wired routers do not support Multicast-DNS forwarding between wireless and wired network segments.

  2. If both your server (iTunes) device and your client (iPhone/iPad,etc.) are on the same segment (i.e. wireless), then iTunes wireless sync should be more or less stable.

  3. If your server and clients are on different network segments (i.e wireless and wired), you will have mixed success with running a stable wireless sync.

My solution was to buy an enterprise firewall (FortiGate) and create one virtual layer-two segment, encompassing all the wireless and wired interfaces on my home network.

This has stabilised wireless sync.

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I'm assuming that iTunes itself is the problem here--and seem always to suggest this, but I would trash my iTunes plist file in ~/Library/Preferences: com.apple.iTunes.plist .

And probably the one in ~/Library/Preferences/ByHost, which will be called com.apple.iTunes.xxxxxxxxxx.plist (some long number) as well.

When apps act up, corrupt Preferences files are often at fault. This used to be common knowledge among Mac users. There are utilities that will check them all, but simply trashing any relevant plists is the easiest first step to Troubleshooting. If there are settings one might forget, they can always be written down first. But no harm is done--apps rebuild their Preferences at next launch, although then of course the user has to create their personal settings again.

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I have the same experience with my iPhone disconnecting from iTunes. It returns, however, after rebooting the iPhone. This faster than the cable connecting and then trying wi-fi.

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