MP3s Won't Load into iTunes

I have a very similar, if not, the same problem. I got my music from other sources, but they were all standard unprotected mp3s with nothing special at all about them. I load them into iTunes fine, and they play fine. But sometimes iTunes will randomly just not play a song. The album art is lost for the song, and I cannot modify it because in "Get Info" the tab for album artwork just isn't there. Most of the time single songs are not affected, it's usually a whole album that will just stop being playable to iTunes.

The songs also disappear off of my iPod, and if I remove them from my iTunes library (but keep the files) and then add them back, well, they simply do not add back. It's as if iTunes didn't even recognize the files as music files. If I keep the songs in my library and try "Convert Selection to MP3," iTunes gives me a useless "Unknown Error -50"

This happens incredibly rarely, but it has happened to me at least four times in the past year, and the problem has never been fixed. I am convinced that this is just a random failure of iTunes and cannot find any possible explanation for it. It's extremely frustrating because there seems to be any cause at all for this problem to occur.

I'm pretty sure I have the same problem as you, copying to iPod was just a problem that came from it.

Your suggestion to convert the ID3 tags completely fixed it for me. I converted the ID3 tags of the affected songs into 1.x, and sure enough, they worked fine. Strangely enough, even after converting them back to 2.4, they worked. I was able to convert the ID3 tags of songs that wouldn't play in iTunes through iTunes (if I hadn't removed them from my library obviously, because once you can't add the songs with messed up ID3v2.4 information into iTunes without first converting to an older version of ID3).

I thank you for solving my problem, and I hope your solution solves your own.

Amazon downloads them to the location set in the Amazon MP3 Downloader prefs.
When it adds the songs to iTunes, if you have iTunes prefs -> Advanced set to *Copy files to iTunes music folder when adding to library*, iTunes will copy the songs to the iTunes music folder location.

If *Copy files to iTunes music folder when adding to library* is already set, just delete the files in the Amazon download folder after it is added to iTunes.

I am also having this problem. I have one DL from emusic.com that just will not add to the iTunes library.

I can play it in other applications, so I know it's not a damaged DL.

I don't let iTunes copy my mp3 files any where. I organize them myself like this: h:\mp3\artist\album.

You can let iTunes do this for you automatically.
Go to iTunes prefs -> Advanced.
Set the iTunes music folder location to I also adjust the file name when necessary to ensure that the track number comes first. .
Tick *Copy to iTunes music folder when adding to library*.
Tick *Keep iTunes music folder organized*.
They will be stored in h:\mp3\artist\album

I also adjust the file name when necessary to ensure that the track number comes first.

Tick *Add track number to filename*.

Message was edited by: Chris CA

I'm having the same problem. Songs that played just last week are suddenly not playing. It is one album in particular, that I only have as downloaded MP3s, specifically Radiohead's "In Rainbows". I tried deleting and recreating the tags and renaming the files. No dice. I don't want to transcode the files (i.e. convert to aac or wmv or ogg) because I'd lose sound quality. I tried downgrading iTunes from 7.6 to 7.4, too -- no change. This is frustrating!