ITunes will not synch all lossless files

I am using Easy CDDA Extractor to rerip my CD's into Apple Lossless format.  Unfortunately I am finding that many, (very many) will no longer synch to my iPod Classic 160.  I can't find any official limitation that would explain this.  Is there one?

Here is the Apple Support Article on iPod Compatible song format.
http://support.apple.com/kb/HT1334?viewlocale=en_US
As for Apple Lossless, you have to update your iPod Classic firmware to version 2 series, if your iPod classic model is after 2009. Your iPod Classic software vesion is shown in the iTunes summary page. You would be out of luck if, it is version 1.1.2, as the hardware is not compatible with iPod software version 2 series.
Have a nice day!

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