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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

Dec 23, 2010 9:01 AM in response to Just Trying To Jam

I'm experiencing similar problems: syncing has ignored audio books on a playlist, only downloading a few plays, and some playlists have disappeared from the list entirely. This is a particular difficulty which I have never encountered before, and because I load my blind partner's Classic, bang go my Christmas presents to her of new books.
Any help would be gratefully received.
Araminta

Jan 30, 2011 4:51 PM in response to jurassic_bark

Funny, I replied to this post a couple days ago, and that post has been deleted... Anyway, I think I found a work around (I won't call it a solution because it is very time intensive, at least if you have added lots of stuff in the last 10 months). Because some songs synched, and other did not, this appeared to be an intermittent problem, but it is always the same songs that won't play. It looks like some songs on my new iTunes just do not want to play on the older iPod, and have confirmed that the song is where the problem is.

I solved this issue by going through my recently added songs, and listing all songs that would not play from iTunes. I found songs that were not playing that were added all the way back in March of 2010. I deleted these songs from iTunes, and re-encoded those mp3s with an extra .2 seconds of silence at the beginning of the song. I used Soundforge on my PC, but I'm sure Audacity or any number of other programs would work for this. To get the cleanest audio possible you will need access to the original media, or uncompressed versions of the song, though. After 2 passes, most of the music that was not working now plays fine on the iPod. I hope they fix this issue soon, though- doing test runs of songs to verify they play properly on both the computer and the iPod is a royal pain.

Feb 6, 2011 6:20 AM in response to Just Trying To Jam

Thanks for the feedback, I was hoping I was not the only one with this issue… hehe

This is ridiculous, what is Apple doing about this? Have they at least acknowledged the problem?

I hate workarounds but to be honest I still have not been able to find a good workaround that works for me on this sync issue. Like I’ve said previously I can not even pin point the problem area, the issue is so inconsistent. Just when I think im on to a common item between songs that are not syncing I get another one show up with different things from the others…..no pattern User uploaded file

Frustrating!!

Feb 26, 2011 11:20 PM in response to Just Trying To Jam

I'm having this problem now after recently downloading the update to iTunes. I have a 1600 song library and can only get 35 of them to sync onto my iPod. The support line at Apple told me to reset my ipod (which I did - didn't work), uninstall then reinstall iTunes (also didn't work). Then tried to tell me it was a hardware problem and the result of something I did.

Has ANYONE had success getting Apple to own up to this? I plan on bugging them daily about this because I would appreciate a product to work correctly. I've only had this model for a year. VERY frustrating.

Apr 5, 2011 11:31 AM in response to Just Trying To Jam

I have same issue. I select the playlist I want. The bar at the bottom moves up given the storage needed for my selections. Then I sync. At the end of the sync the capacity bar moves back down. Only about 25% of items from playlist were synced. I am a bit new to iTunes and particularly playlists but this is quite frustrating. I wanted to use playlists to overcome another shortcoming: the way iTunes handles classical music labels.

Apr 7, 2011 6:05 AM in response to Just Trying To Jam

Have new Ipod Classic 160Gb. Itunes sync OK to nano and to older Ipod Classic 80gb but not to the new Ipod. Tried resetting it about 10 times. Have 12,500 tracks., gets to about 10,300 and then stops. States Fault 69. ( Different track each time) Tried removing tracks but once again sticks. Only thought is , is it possible to load older version of Itunes

Oct 14, 2011 11:05 AM in response to Just Trying To Jam

I was having this problem today, trying to sync my itunes library to my new 4s... it would stop on "I will dare" by the replacements every single attempt, and leaving out 278 other songs after replacements. I could see the song descriptions in my iphone, but the actual mp3 was not there. So what I did was go to my music, made a new playlist called "Jukebox", selected all, and dragged it to that playlist, then checked the "selected playlist" box on the music sync screen, then checked "jukebox" and a couple seconds later, everything sync'd just fine.


Rock it out 🙂

Oct 15, 2011 12:58 PM in response to Just Trying To Jam

WIndows 7 solution 🙂

I had a similar problem, I put 32 albums on itunes, but it would only sync 4 to my ipod. This is a new PC with windows 7, so I figured something must be strange happening due to this format as I checked my old PC with Windows XP and my ipod synced just fine. So I looked at those 4 albums, trying to see why those were the only ones that were syncing, and as it turns out those were the only 4 that were on my C drive (3 in my downloads file, and one in my itunes file). The other 28 albums I had tried to drop and drag from my external hard drive. So I dropped and dragged those 28 to my itunes library file (found in My Music). I then had to clear all 28 albums out of the itunes library and then added these 28 albums back one by one. Voila, upon syncing, all of the albums now appeared on my ipod. In other words, the music (or files) must be on C drive, ideally in the itunes folder.

Oct 19, 2011 5:28 AM in response to Just Trying To Jam

Same problem for me also since itunes 10 update.


Purchased songs on iphone, created a playlist, synced with the mac but the playlist does not appear in itunes. The new songs are in the music list but the playlist was not created so i had to trawl through the music list to find the songs i had purchased and create a playlist on the mac. so now i have duplicated everything.


Come on Apple sort it out!!!!!!!!

Oct 20, 2011 9:25 PM in response to Just Trying To Jam

I FOUND A SOLUTION. at least, I was having the same problem as yall, and I found a solution that worked for me, I hope it helps yall too.


My issue was that music would sync to my devices, but some of the playlists would not have all of the songs in them that they should have had. I looked at the playlists, that I was having issues with, and they were all complex smart playlists. Meaning they had multiple levels of conditions in the smart playlist settings, and itunes 10 does not seem to suppor that. To fix it, I went through all of those smart playlists and made new smart playlists that had the same (or as similar as I could get them) conditions to my old playlists. I then re-synced my devices and all my songs appeared in my playlists.


I dont know why, but itunes 10 no longer supports some of the smart playlist rules that older versions of itunes did, so hopefully updating your smart playlists will fix this problem.


Best of luck guys.


P.S. if you dont know what I mean by 'complex' smart playlist, here is an example of what I mean:

User uploaded file

Oct 25, 2011 8:14 AM in response to Just Trying To Jam

I had the same issue as everyone here. Certain songs from certain playlists would not sync. My iPhone 4 did not have this problem, but my iPhone 4S does. A quick fix is to check the box labeled "Manuall manage music and videos" under the device summary screen. This sync'd the remaining 335 songs onto my iPhone and I was able to drag my iTunes playlists onto the device and all the songs were there. Hope this helps!

Itunes won’t sync ALL playlist songs to IPOD

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