Trouble transferring iTunes library to new external hard drive

Have you tried starting iTunes and holding down the OPTION key, which will bring up a window that allows you to choose the library you want to load.

Were both your library and music itself on the external, and copied across to the new one?

That is weird.

Not to be a stickler, but it's worth clarifying some jargon to make it easier for yourself and others more familiar with iTunes to help you.

The library file, per se, is the file (with extension .itl if your Finder settings display file extensions) that iTunes reads to get all the information about your music files, including their location and metadata (Artist, Genre, Track number etc) without having to actually read the music files themselves each time. This is generally in the "iTunes" folder, which is itself generally in the "Music" folder, either on the main hard drive or, as in your case, on an external. Inside the "iTunes" folder is normally where you'll find your music, in the folder "iTunes Music", the exact location of which is specified in iTunes->Preferences->Advanced->iTunes Music folder location. This is your library of music, as opposed to your .itl library file.

Semantics over - let's try and resolve this!

My first question is about the new external - is it formatted as FAT32 or as NTFS? Macs can read files from a drive that is formatted as NTFS, but Macs cannot write to files under such a system. Your external needs to be formatted as FAT32 for this (assuming you also need the data on it to potentially be readable by a Windows PC at some point, otherwise there is a Mac-specific format you could use which Windows cannot understand at all), and this could foreseeably be the reason for the apparent weirdness because library files definitely need to be read and written to - every time you change anything about a song in iTunes, or even listen to a song, its entry in the iTunes Library file is updated. So iTunes may have been checking for this and not allowing you to select that library file because it knows it won't be able to write to the file.

You can check the formatting of your new external by right-clicking the icon in Finder and selecting Get Info. Under "General" you will see a section called "Format".

Well, at this point the best I think can tell you is what I would try - which is to start from scratch again using a procedure that has worked in the past.

This method assumes you can still access your library functionally from the old original hard drive - can you? By which I mean can you choose the iTunes Library file on your old external and open it and have all the music still found, just as it all was before this escapade began?

If so, then this site has your solution: http://lifehacker.com/238296/ultranewb--how-to-move-your-itunes-library-to-an-ex ternal-drive

If this doesn't work let me know and we may have to do this the long way.

Well iTunes is really nothing but a database... If all your music is in the folder probably the easiest thing to do is just rebuild the database...

this is the same prolem i am having, i am moving from a PC though. almost all of my tracks are working. but maybe a 1000 arent.... the files are in the right place. but it wants me to locate them anyway...
Play count is very important to me!

I tried a quick test since people seem to think 'play coun't is important. I started a library with a song and played it 3 times, them put it in a playlist and exported it. Then I created a new library on another drive and imported the playlist. It copied the song to that drive and kept all the added data intact.

Well I can think of two things. One might be that all your music isn't stored in the iTunes Music folder. You could try consolidating the library before you try moving it. Two would be put everything in a playlist and export it. Then import that playlist to a new iTunes on the other drive.

Yeah - it may be well worth your while to consolidate your library before following the instructions on that link, just to ensure that all your music is actually in one place. You'll need to check in Advanced Preferences that both the boxes are checked that give iTunes control over managing your files and copying them into the iTunes Music library folder when imported. You should also check that the specified iTunes Music folder is the original one if you'd previously changed it during all this.

pqh alluded to my nest suggestion is that link doesn't work, which is to just start with an empty new library on the new external and just import all your music again. This would probably raise some issues, that some responses here have already suggested solutions for, like play counts and playlists and artwork (unless you have the art embedded in the music files themselves - by default iTunes doesn't do this, but saves the artwork in the Album Artwork folder which iTunes then references. This is fine if you're always going to use iTunes, but if you ever move to another platform the artwork doesn't come along. There is a free script at Douscripts.com which will scan through your library and embed the artwork downloaded from iTunes into each music file)

I was having basically the same problem. Here's what I found on it:

A very common mistake made by most users is to simply try and move their entire iTunes Music folder to a new location and update the iTunes Music folder path in iTunes’ preferences. In some cases this may work, but in reality you will risk iTunes losing track of some or all of your music files in the process.

The reason for this is that iTunes stores the entire full path to each music file in its library database. If you move that file somewhere else, then iTunes won’t be able to find it, and the result will be a broken link to that file, shown as an exclamation mark in iTunes immediately to the left of the track listing. If you try to select a track with a broken link, iTunes will notify you that it cannot find the file, and provide an opportunity to locate it yourself.

Selecting “Yes” will allow you to browse for the file, and iTunes will link the current entry to that specific file. This can be a viable solution for a few broken links, but you can well imagine that this could become very tedious if you had hundreds or even thousands of files in this state.

Should you find yourself in this situation, the simplest solution is generally just to move your iTunes Music folder back to its original location. iTunes still has the complete path to each file in its database, so if you put the actual files back, it should have no problem finding them again.

Note that users who have a completely “Managed” library configuration may be able to get away with using this method to move their library, however it is still not the recommended solution. The reason this method will work in this case is because iTunes will actually look for any missing tracks in their default location under the iTunes Music folder path before deciding that the links are broken. So, if your tracks are organized in the way that iTunes expects to see them, then it will be able to locate them in the new location. However, this solution is rarely completely reliable simply because it is not uncommon for users with large libraries to have a few referenced files due to changes to iTunes preference settings or even inconsistent behavior with older versions of iTunes.

I didn't write this up though, I found all the info here: http://www.ilounge.com/index.php/articles/comments/moving-your-itunes-library-to -a-new-hard-drive

Now I just have to spend another 7 hours moving my 500 gigs back to where they were, then another 7 moving them back here yet again!