Not sure. But keeping in mind iTunes cannot import MP3Pro format files, though they are not so common.

Sometimes iTunes stops importing directly from LW, which usually happens after LW has been running for some time. I suspect there's some Java memory issues which stop the process happening. Closing & reopening LW should fix it. Else turn iTunes importing off, press apply, then turn back on in LW's prefs.

A possibility is that the mp3's you are having problems with are not mp3's but viruses (mini programs.) That would cause permission errors with OSX attempting iTunes to copy them. See no. 2. (n) & (o) here: http://www.gnutellaforums.com/open-d...uld-aware.html