Assuming the iTune files are either AAC or ALAC and not MP3, and without
more details on working /not workgin system (h/w, OS versions , LMS
versions) this "feels" like the AAC transcoding chain is broken.

Older SB player such as Boom and Reciver  cannot play AAC natively so
they need to be trasncoded.  Newer player such as Touch and have AAC
support but maybe not ALAC support.  No idea about Squeezepad.

Checking WebUI Setting/Advanced/FileTypes to see whether you have
support for AAC and ALAC (apple Lossless) via Flac through "faad/flac".

Next also try using a Terminal window test whether the flac and faad
executable in the LMS Bin directory actually run on your system.


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