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Itunes won’t sync ALL playlist songs to IPOD

I have hundreds of songs from multiple playlist that do not sync to IPOD. I will write a few notes i have on this and see if anyone can help.

NOTE-My Itunes and IPOD playlist have previously always been sync'd exactly the same. I do not know exactly when the UN-SYNC began but i believe it was after ITUNES 10 upgrade.
NOTE-I have tried so many troubleshooting techniques but i can not find the culprit. At first i thought it was corrupt mp3 files but that was not it.
NOTE-There does not seem to be any rhyme nor reason for the issue regardless of bit rates, file size, encodings, etc..! I usually find work arounds with ITUNES/IPOD quirks, but this one has me stumped and Im so **** frustrated!!
Things tried - Restored an old library (Itunes 9) prior to ITUNES 10 upgrade. Result= NO change.
Things tried - Exported library, then wiped off old library, created NEW library and imported library. Result= NO change
Things tried - I was getting desperate so i decided to start a new library and recreate my library from scratch, in hopes of individually importing playlist. Anyone that has ever done this knows how much of a pain this can be especially with 56K songs not too mention all the wma to mp3 conversion times. Result= Well regardless of all the hope i had this would resolve the issue once and for all this was useless! It turns out for some reason Itunes 10 decided to rename the mp3 files it had converted from wma files differently than it had back in ITUNE 8 when i created the library years ago. Those of you that know how important file naming/paths is, understand this would have made my years of playlist worthless unless I went to each song and redirected the path.. NOT happening. Therefore I was so ****** I decide to scrap this test.(Guess this another separate issue i will look into)
Things tried - i have the same problem on two separate IPOD's, my 160Gig and my older 80Gig.
NOTE-After finding some of the songs that were not being sync'd i started to troubleshoot those, but the weird part is for some reason either by coincidence or something the particular song im investigating all the sudden sync's on IPOD and i did nothing to it. FYI - I had hit IPOD sync several times through the investigation so who knows if that had some sort of effect!!
Summary: I’ve given this due diligence and confident it is related to itunes10 upgrade. Help would be greatly appreciated.

Windows 7, Itunes Library itl file and ALL songs reside on external drive. 56K Songs Plus in Music Library

Posted on Dec 23, 2010 7:23 AM

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16 replies

Nov 11, 2011 3:40 PM in response to Syriel

Fixed it, I think, first of all if I select my iphon4, tick the sync music box, tick entire library, in the capacity bar at the bottom of screen.it appears to only be syncing 3GB of music, I have about 40GB, if i select music from the library, then all artists as I scroll down I see that for some reason since updating iTunes has removed the tick from loads of my album and songs, I've now gone to Edit, select all, then, Edit check selection, that ticks them all, now when I select my device and try to sync entire library it warns me that there's not enough space, so I select some music and I syncs properly now, hope this helps

Itunes won’t sync ALL playlist songs to IPOD

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