iPod Need help with iTunes (duplicate files & broken links)

Ok, please bear with me as I try to explain what the problem is (new to macs & still stumbling and fumbling around rather ineptly).

When I switched I moved all my music to the new laptop using a USB drive. I don't remember exactly how I did that apart from the fact that first I had to move the music back from an external HD to the old laptop (badly running out of space there so kept iTunes on external HD), then I copied it to the USB & then from the USB to the MBA.

So amidst all that copying back & forth I must have created copies of most (all?) my music files b/c when I look in the iTunes media folder (the music folder, not the library) I see two of each m4a file there with almost same file name (one file has the number "1" at the end of the name before the extension). Apart from the fact that those files take space they're annoying the hell out of me

The other problem I keep having since switching is that links get broken: there's the little exclamation mark next to a track, when I click on it it says "can't locate file" or similar; when I navigate to the music folder & open the file the link gets repaired (that's when I discovered the duplicate files).

So I guess my questions are:
1) Are those really duplicate files that I created or is this something iTunes does for its own mysterious purposes?
2) Can I really delete those files without inflicting damage on the music files and is there a quick way to do it?
3) Why do links get broken? Never had this happen before... and again, is there a quick way to do it or do I have to search for and open each file manually?

Oh, and I have a few other niggling issues, e.g when I switch to a list view iTunes rearranges the tracks in an album from last to first. if I switch to album view it fixes itself so I stay there but, again, it bugs me

A quick aside: love my MBA and the OS but there is definitely a learning curve

P.S. Just saw the sticky at the top of the forum: seems I posted in the wrong place, sorry & moderators, please feel free to move the thread to the mac app forum.

No takers, huh?

After some googling around I can answer part of my own question. The files with same names & an extra number in the file name seem to be duplicates. Just deleted about 350 of those (finder -> music folder -> search for files with 1.m4a in the name and hit command+del - worked like a charm). I must have created them either when when I moved my music or by somehow accidentally transferring from an iPod.

The appearance of broken links is still a mystery though.

In general, file management is the biggest challenge for me since switching. I haven't figured out where files & folders go when I do something to them. Sometimes they just go *poof* (nothing critical so far, fortunately). As a long-term XP/W7 user I am used to specifying exact paths. The other day I was converting a playlist into mp3s & it seemed to work but for the life of me I could not find the actual mp3s until it occurred to me to look outside the playlist into the actual music folder

One last observation: my problems with iTunes started a few weeks ago when I checked all those "copy into iTunes folder" & "keep library organised" & "consolidate" options in preferences.

I'd like to hear from people who manage their own iTunes libraries. I am seriously considering going back to this, especially if I can figure out a way to do it without having to nuke the whole music library and starting from scratch.

Still talking to myself here Either there is no solution to my issue w/ iTunes or this is a common question with a solution that everyone (except me) knows about and is not telling.

Anyway, I fixed a bunch of broken links a few weeks ago and then last week about 350 new ! appeared out of the blue. There's no rhyme or reason: the dead tracks are in albums I've imported myself, in tracks I've bought from iTunes, in tracks I transferred via USB and via iPod, in tracks that are in playlists and in tracks that are not in playlists. No pattern.

At least I found a faster way to fix the dead tracks for whole albums: instead of opening tracks one by one open Finder, search for the album name, drag all tracks from that album to iTunes & then delete the duplicate dead tracks (if time permits).

Since it seems all problems started when I first moved to an external HD I've unchecked the "keep iTunes organised" and "copy files to iTunes" in preferences & have gone back to organising music myself (something I'd done for five years on a Windows laptop without any issues).

I'd love to hear from other people who manage iTunes libraries themselves. If someone knows of a post or website that explains in detail how iTunes organises files please point me in that direction.

HazyCloud said:

FWIW, the broken links are because your iTunes library file saw those files in a different directory. I had the same issue recently when switching to OSX. I moved all of my music to an external and then pointed my iTunes to my existing ITL file. While iTunes saw all of my media, everything that wasn't in the "iTunes" folder on my machine had broken links. The easiest way to fix it was just delete each artist and re-import.

It seems that if you move your media, iTunes will automatically create broken links to all of the media you moved. I did however notice that even if you rename your external that houses your media, it doesn't affect iTunes.

Once you get everything the way you want it, leave it be. It took me over 30 hours one weekend to re-import and fix any broken metadata. As soon as it was complete, I bought an online backup solution to insure all of my work wouldn't go down the drain in the event of a HDD crashing.

Click to expand...

Thanks for the explanation, it makes sense & is in line with my experience (problems started when copying & moving iTunes files). And I hear you on the leaving things be after fixing (it did take me quite a few hours to get things back to normal).

I plan to use iCloud for back up/storage because all my non-iTunes-bought stuff is easily recoverable (CDs I own anyway).