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This question has been asked 1000 times over on other forums, yet none of them have been answered properly. So I'm turning to the great people at TR to shed some light on the subject.

I've got a customer that insists on buying a new iPod (for whatever reason) about once a year. So we always go through the hassle of copying all of his music off of the iPod to his current computer, and then syncing it back to the new device. Well he got tired of using iTunes and wanted something different to do this. I slapped Winamp on his system not knowing what to expect and he loves it... however, the same problem persists. He has well over 8000 songs and only about 6500 of them sync.

I went through his library and found a few albums/songs that I could fix that suddenly allowed them to be sync. For example "Blue Oyster Cult" had an "O" with a dipthong, so the iPod freaked out over the none so standard character. But that only accounted for 31 additional songs and it showed up in the failure to sync menu so it was an easy mistake to catch. I ran a Winamp AutoTag on the entire library hoping it would correct a lot of those issues but it didn't appear to do anything that allowed for more songs to sync. With a library of this size, it just seems stupid to try and manually change everything and check each song for problems. All of these songs seem to play fine in Winamp or iTunes, but I don't even know which ones aren't syncing.

Does anyone know of a good method to check all songs for iPod sync-ability. Perhaps a program that can scan through or notify you if a song has incorrect tags or something along those lines? I'd hate to tell him he is SOL, but I'm also sure they don't want to pay me for many many hours of song by song checks.

Try this program.

Two questions: which iPod is he using and what is the OS on his computer? He might also need the latest version of iTunes.

He wants to avoid using iTunes anymore, can't stand the interface apparently. Its Windows 7 SP1 and its an iPod Classic 160gb, the old one is a 120gb and he is not even remotely close to maxing either or them.

OK. Have him look here and here.

Also consider this one.

He likes Winamp oddly enough, and I'd hate to ask him to switch to something that I have ZERO experience with... then again I rarely use Winamp and don't even have it installed on this system. The problem isn't with the player as this was the same issue he experienced with iTunes. I just think all in and all that iPods are PoS that like to lock down users from playing or syncing music that's not purchased through iTunes itself... sad thing is that most of it was purchased from there. He may have ripped a good number of them from his own personal CD collections, which may be the ones not syncing.

I have read that there is an iPod plugin for WinAmp. That may need to be upgraded to accommodate the newest iPod Classic 160GB. Try this and this. He may be forced to try a solution that does not involve WinAmp though, if only to get around this issue. I have used XPlay from MediaFour and that worked great for me. This is the successor to XPlay, which should work great on his system (especially once he ditches iTunes off his PC).

My only songs that ever fail to sync are just songs that have changed their folder location (usually due to me cleaning up my computer file locations)

However doing the re-sync thing typically results in double ups of the same songs. (some of my albums are repeated 3x on my iPod & iPhone)

yogibbear wrote:

My only songs that ever fail to sync are just songs that have changed their folder location (usually due to me cleaning up my computer file locations)

However doing the re-sync thing typically results in double ups of the same songs. (some of my albums are repeated 3x on my iPod & iPhone)

There is a way to solve that issue. According to Maximum PC for August 2012, one tip allows you to clean that up in iTunes. In iTunes, go to File > Display > Exact Duplicates and all the duplicates will be shown. You will have to choose each one and hit Delete.