Just spent hours figuring this out and thought I'd share this bit of
information. In my setup I'm syncing the iTunes directory on my MacBook
Pro to my Ubuntu server, and relying on the iTunes integration to load
the tracks from "iTunes Music Library.xml". My "Music Folder" is set to
a different folder that contains some music that I never bothered to
copy to my iTunes Library. I had a problem where a lot of tracks would
not be recognized by SqueezeBox Server.

Turns out that if your iTunes library goes back a long way,
capitalization problems can arise; e.g. the XML would refer to a file
"Beyonce/Dangerously In Love/01 ...." where the actual file would be
"Beyonce/Dangerously in Love/01 ...." (note 'In' vs 'in'). My Mac
doesn't have a problem with that as MacOS X is case insensitive by
default. Linux, which is case sensitive by default, simply doesn't find
the file. Normally this isn't a problem as typically you'd select the
"iTunes Music" directory as your "Music Folder" and Squeezebox server
would simply scan those files anyway, though you might notice some
issues with trackstat on those tracks.

Now there's two ways to fix this; either reformat your media partition
case insensitive, or use FUSE and ciopfs to create a case insensitive
overlay filesystem. I chose the latter option and it's working great
now. Just make sure you start from an empty directory, mount it using
ciopfs and copy (or move) all your music to that directory. ciopfs
assumes the contents of the source directory is all lower case, so you
can't just ciopfs your existing "iTunes Music" directory.


-- 
evinyatar
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