Unable to sync some songs to 80 GB iPod Classic

I'd tried that as one of my dozens of iterations / variations and got an instant hang of iPod, iTunes and the sync process. iTunes continues to show it is syncing even though it isn't, and the iPod says 'do not remove' even though that is the only option I have to be able to subsequently communicate with iTunes or get back control of my PC.

Since my original post, I formatted & restored the iPod yet again, duplicated the 4,000 song playlist I had been trying to sync, exported a list of the 114 'problem' songs, then went through it and manually deleted the 114 songs from the duplicate playlist, then synced the iPod and it ran to successful completion. Attempting to then manually add any of the 114 'problem' songs causes an immediate hang. I fail to understand the logic if I have say 5 songs from one album and 4 sync OK when one does not.

Appreciate you trying to help. However, no luck with first part of your suggested action. I do not us iTunes Match.

I decided to follow your suggestion with 2 different songs; delete both from iTunes library, then reload song#1 manually and reload song#2 as part of iPod sync.

Reload of song#1 hung iTunes after about 35% of song. I deleted song#1 from iTunes library again, then tried syncing the iPod to reload song#2 and it hung iTunes at about 55% of song. It is interesting that if I repeat any of these actions, any individual song always hangs at the same point (eg 35% for song#1).

As yet another variation, I again deleted both songs from iTunes, then re-input them to iTunes from the original song files in Windows and tried to manually copy them to the 80GB iPod. Once again song#1 hung at approx. 35% and song#2 at approx. 55%. Both of these songs happen to come from two different CDs I own, and other songs from these CDs sync without problem. I haven't gone as far as re-creating the Windows song files for these two songs - trying to do that for 114 songs from multiple sources would be a completed pain.

My iTunes library of 12,500 songs has been compiled over several years from multiple sources; hundreds of CDs, a small number of LP tracks added using Audacity, maybe a couple of hundred purchased from the Apple store, plus a gazillion downloads from Artist websites, other paid or free download websites, YouTube, Bit Torrents, full concert audio edited into individual songs using Audacity, whatever. The bulk of the library that syncs without problem to either iPod is the same mix as the 114 problem songs (and in many cases from the same original CD / Album / Website / Torrent source).

Data from the 114 problem songs that fail to sync manually or otherwise shows the music comes from 96 Albums by 83 Artists. Bit Rates are a complete range including 128, 157, 160, 174, 192, 200, 256, 320 kbps, and Kind is almost a 50/50 split of AAC Audio Files / MPEG Audio Files with just a few variables like 5 Protected AAC and 3 Purchased AAC. A quick skip through File Types shows the majority as .mp3, a large number of .mp4a plus a small number of .mp4p

Skipping through the successfully synced 3,800 songs shows exactly the same variable mix of all of these values or File Types.

Thanks for persisting with help.

Once again, inconsistent results to draw any conclusions from. As you suggested I deleted all 8 songs from iTunes and my Windows music folders, re-downloaded from iTunes Store, then manually dragged them from iTunes to the 80GB iPod. All but 2 migrated successfully, so thanks for that.

I re-deleted and re-downloaded the 2 failed songs from iTunes Store, tried to load them to the iPod one at a time and........ nothing. The songs did not migrate, and iTunes showed no info / status / error message.

The 6 successfully migrated songs comprised 5 .m4p format and 1 .m4a. The 2 failed songs are both .m4a files.

Ho-hum. 6 successes, 2 no-answers, and only 106 (not 96) to go. Thanks again for trying.

Thanks for persisting with help.

Once again, inconsistent results to draw any conclusions from. As you suggested I deleted all 8 songs from iTunes and my Windows music folders, re-downloaded from iTunes Store, then manually dragged them from iTunes to the 80GB iPod. All but 2 migrated successfully, so thanks for that.

I re-deleted and re-downloaded the 2 failed songs from iTunes Store, tried to load them to the iPod one at a time and........ nothing. The songs did not migrate, and iTunes showed no info / status / error message.

The 6 successfully migrated songs comprised 5 .m4p format and 1 .m4a. The 2 failed songs are both .m4a files.

Ho-hum. 6 successes, 2 no-answers, and only 106 (not 96) to go. Thanks again for trying.

FINALLY, after my 80GB sync problem list has grown to 144 songs and 400+ people have viewed this problem thread without offering a solution, I discovered the answer whilst trying to sort out another issue that has been all over various Apple forums for several years (songs stop playing mid-track, not playing to completion). Solution to both problems (at least for me) ..............

In iTunes on PC
1. Select and Highlight problem Song
2. Click on File on main Menu bar
3. Select Convert from drop-down Menu
4. From side-bar Menu, click Create AAC Version (even if original songfile is .m4a rather than .mp3)
5. iTunes Playlist will show two versions of Song; original problem version plus new AAC Version created in previous step
6. Delete original problem version from both iTunes and Windows (Delete + Move to Recycle Bin)
7. Sync iPod with iTunes

On iPod
8. For Problem 1 (this thread: unable to sync some songs to iPod) After iPod Sync completes successfully, verify that songs that previously would not sync are now present on iPod
9. For Problem 2 (songs not playing to end of track) Select and Play new AAC Version (.m4a) of problem Song created above to verify it plays to completion

Hi,

Yes you need a ton of patience. It took me literally years of workarounds until I stumbled across a 2009 posting on a different discussion forum which gave me a nudge towards solving my problem. Now I have resolved my 144 song issue completely, my 80GB iPod syncs to normal completion, and if I have any new problem songs I just run through the AAC conversion process I listed.

All of my 13,000 files of music / podcast / foreign language stuff fits easily on the 160GB iPod I use at home, but it won't all fit and I don't need all of it on the 80GB I use in the car. So this is how I got there (it takes longer to type this stuff than to actually do it)...................

Step 1. I created a Playlist called 80GB of just under 5,000 songs for the car, and set the summary page (iPod icon at top of iTunes menu > iPod from drop-down menu > Options) for the 80GB sync to Sync only ticked songs and videos, then after selecting iPod > Music checking only the 80GB playlist before clicking Sync

Step 2. The sync process would hang mid-way thru some random song. Despite the Do not disconnect warning, the only way to get out of the hung iTunes was to disconnect the iPod.

Step 3. I created another Playlist called Lost Trax. You can obviously call yours whatever you like, like F'ing annoying iTunes problems.

Step 4. I dragged the problem song into the Lost Trax playlist, then made sure I deleted it from the 80GB Playlist before running the iPod sync again. Over the years I went through the Step 2 to Step 4 loop over and over again to get the 80GB iPod to sync to completion, until I had 114 problem songs when I first posted on this Forum and 144 when I found the solution.

Step 5. The solution I posted above on 14th August. After running through the process 144 times, once for each of the problem songs, I now have zero files in my Lost Trax playlist and my 80GB iPod syncs to successful completion every time.

It's a pain in the butt (US), or a pain in the arse (I'm a Brit in the US), but it works. Best of luck!

Just to clarify my earlier posting....

Step 4 Delete only from my 80GB Playlist, not from iTunes.

Step 5 After running through AAC conversion process for each of Lost Trax playlist of problem songs, adding them back into the 80GB Playlist before syncing again.

I have never had any similar issues with my newer 160GB iPod, which happily sync'd all of the 'problem' songs without error. Mind you, I never had this problem with the original 60GB iPods I owned way back when. Despite multiple posts on this and other forums mentioning bad hard disks, battery problems, or other iPod hardware / software issues, none of the suggestions in these postings was of any help. I was never convinced the cause of the problem was iPod hardware related.

Since you seem to have a similar if not identical problem, I'll be interested to learn how you get on. Please report back.