I've searched for this topic and seen a few mentions of issues with Apple Lossless, but nothing similar to my issue.

PC running Windows XP SP1, Squeeze Server Version: 7.4.1 - r28947, Squeezebox Boom, music files created via iTunes, music stored on NAS drive hooked to Linksys router. PC connected to router via Ethernet.

Problem - I use iTunes (with SS set up to use iTunes) and the majority of my music is Apple Lossless. It has been working fine with the Boom until recently. The other night I went to play something and the Boom started jumping from track to track in the playlist without playing. When it finally stopped, it said "can't read file" and displayed the path to the music folder. I started testing various tracks with the same results, until one finally played, which I then realized was an MP3 track and not an m4v. Same results with Soft Squeeze. Since I suspected maybe something was amiss with the files, I made a separate directory on the NAS outside of iTunes and dragged a couple of MP3 files into it as well as a couple of Apple Lossless files. Has SServer scan that folder and *both* types of files played fine. Tried emptying cache, etc., in Server and re-scan iTunes library but get same results - not playing Apple Lossless files put playing MP3 files. The problem had occurred first in an older version of Server (7.3?), so I thought upgrading to 7.4.1 might help but it did not.

Any ideas about this problem? Any help would be appreciated.