I recently bought a new iPod classic to replace my 5G (with video). After setting up the iPod, it refused to sync automatically with iTunes as my 5G had -- it would eject within seconds of being connected, so I had to press Sync immediately to get it to sync.
Last night, I got bored and went to poke around in the Preferences. Lo and behold (in iTunes 7.5), the iPhone pane has turned into the Syncing pane, and there's a checkbox with the text "Disable automatic syncing for iPods and iPhones." Unchecking it solved all my problems.
[robg adds: When I first read this, I thought it was one-time occurrence, as none of my machines have had this box checked by default. However, three additional hint submissions on the exact same subject make me suspect that something else is going on, so in case you've been having auto-sync issues, here's the solution.]
Last night, I got bored and went to poke around in the Preferences. Lo and behold (in iTunes 7.5), the iPhone pane has turned into the Syncing pane, and there's a checkbox with the text "Disable automatic syncing for iPods and iPhones." Unchecking it solved all my problems.
[robg adds: When I first read this, I thought it was one-time occurrence, as none of my machines have had this box checked by default. However, three additional hint submissions on the exact same subject make me suspect that something else is going on, so in case you've been having auto-sync issues, here's the solution.]
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