Over the holidays, I encountered an unresolved problem where iTunes 7.5 doesn’t automatically launch and sync with an iPhone when the phone device is attached to a Mac running Leopard (OS X 10.5). The launch failure occurs even though auto-sync is enabled in the iTunes preference window (see below).
So far, the only way my customer has been able to sync his iPhone is to first start up iTunes manually. As part of the troubleshooting process, my client deleted the iTunes preference list files that appeared in /~Home/Library/Preferences/ and its sub-folder /ByHost. Doing so, however, has not resolved the issue.

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By: IPhone » Attaching iPhone to a Mac doesn’t auto-launch iTunes on January 5, 2008
at 3:35 pm
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By: I Organize » Blog Archive » Attaching iPhone to a Mac doesn’t auto-launch iTunes on January 5, 2008
at 3:45 pm
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By: IPhone » Attaching iPhone to a Mac doesn’t auto-launch iTunes on January 5, 2008
at 7:11 pm
I had the same problem: I unchecked the option, quit out of iTunes, unplugged my iPhone, launched iTunes, plugged the iPhone back in, checked the option back in and iTunes said:
“To use this function, iTunes Helper needs to be installed. Would you like to install iTunes Helper?”
I did that and… it’s working again. I think I’d deleted iTunes Helper from my startup items to speed up the boot up process. Hope this helps somebody.
By: Jorg on October 5, 2008
at 5:19 am
Jorg is right, I had the same problem after upgrading to leopard and his solution worked. Another problem I had was that when syncing in it said ‘your computer is not authorized for the apps on your iphone’ (or something like that) and offered to delete all my apps for me. It had a button to click that said authorize but when i clicked that it said ‘your computer is already authorized’ and then went back to the ‘your computer is not authorized’ screen. the solution seemed to be to reinstall itunes.
By: nick on December 10, 2008
at 1:34 pm