iTunes will not sync mp3's to iPod.

[agravlin]

I'm having a little trouble here.

-iTunes will not sync some mp3's (all legal from the creator's website - I don't steal copyrighted material) from my hard drive to my iPod. I tried both "Import..." and "Add File to Library", although I'm not sure of the difference. It does actually sync. It just doesn't sync any MP3's I add from my hard drive.
-The songs will show up in the "Music" tab's lists, and I even tried editing their info to make them into tracks on one album.
-It didn't work with 7.1.1.1 that I used yesterday. I upgraded to the most recent version today, and it continues not to work.
-The files are in the proper format. There is no "Convert to MP3" option because they are already MP3's.
-I can rip a CD with iTunes and transfer it to the iPod, and iTunes will sync photos and podcasts just fine.
-Not sure if this matters, since the files aren't from iTunes, but the iPod has been authorized in iTunes for months.
-I tried both in and out of Hard Disk mode. No luck either way.

Again, it syncs everything except MP3's 'added to library' from my hard drive.

[cjmnews]

That's odd. I just made a playlist of all my MP3s (all 12 that are not podcasts) and they all synced just fine. Played too.

My guess is it's probably a tag issue. Try right clicking on one of these files and choose Convert IDs tags. Use version 2.3. Then sync. I think that will fix it.

[agravlin]

Converting them to v2.3 ID Tags did not work.

Also, I just remembered that one of the MP3's I'm trying to sync was actually purchased from iTunes several years ago. It won't sync either.

[cjmnews]

There used to be something on Apple's web site about old files no longer working. I can't find the reference anymore.

Sorry I couldn't help.

[bobb-mini]

Me thinks obsolete MP3 encoder used or VBR encoding iTunes doesn't like.

[agravlin]

So how do I fix the problem?

By the way, there are no error messages, such as the frequent "Your file was not transferred to the iPod because the iPod cannot play that file type." that people report. It just skips over the MP3's I added to the library.

[agravlin]

Oh well, thanks anyway.

[bobb-mini]

Nope. Sometimes iTunes just ignores that it doesn't like. How to fix? Re-encode bad MP3s.

[LDiablo]

As Mr. Brevity (bobb-mini, aptly titled insanely sarcastic LOL) explains, there seems to be something corrupt in the files you're attempting to load. I've just figured this out today after conferring with my deduction ability and these forums.

I recently ripped several CDs from my collection and after loading them into iTunes and then attempting to play on my way to work in the car - first song was missing from most of those I'd ripped and added as complete folders. Went back and confirmed the songs were in the folders, played the songs using Media Player, and then tried to load them as single files. Got the shrug off from iTunes that you describe, agravlin.

After putting some thought to it, methinks what happened was that when I ripped in Media Player (just switched to it as my rip engine after dell jukebox changed drastically), it had started playing the first song and even though it created that MP3 and was playable, the song info didn't register correctly and thus iTunes sees it as something smelly and won't touch. That's my conclusion anyway.

I then went in and re-ripped the missing songs, making sure they weren't playing. Double checked properties to ensure the song info was in the properties, and then re-loaded.

One tip - even though it took a little longer, I re-ripped the entire CDs and then deleted and replaced the whole thing to preserve the song order. Otherwise, loading the one song will usually move it to the end of the song list for that album. ANd when you're used to an album's order after listening to it for years, it just don't seem right to send one to the end of the line.

Hope this helps.