Well, obviously, something is up. I’m not a Mac or iTunes dude, but in the past, it’s been noted that a Mac, when transferring files to a device, creates “ghost system files” that often will clog (better: choke) a device (any DOS-oriented device, not just the Clip). The solution: use freeware software such as KopyMac to transfer the files–it deletes the ghost files (and is easy to use). Note: apparently, KopyMac is fast disappearing, as the developer no longer is working on it; if you can’t find it (or just as an alternative), freeware Hidden Cleaner also has gotten high marks. Perhaps try one of the above (and let us know the results)? P.S. There are a few other ways to eliminate the ghost files, that I don’t have under my belt (such as using terminal emulator or something like that, on a Mac?)–you could try a search here (box at the upper right).
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