melda4824 wrote:
I got my current laptop about 3 years ago and transferred everything from my iPod to the new computer when i first plugged it in.
Perhaps that's when the Sync message problem began. It's a common issue, we see it often here.
This might seem to be a long, complicated post, but it really isn't.
melda4824 wrote:
... i see a folder named "previous iTunes libraries" which seems to have all my songs in it. Am i ok to sync then, even if that gets rid of my 'old library' music? i should be able to put it back on using that computer folder right?
Whoa, hang on. That's not how iTunes works.
I too have a folder named Previous iTunes Libraries. Don't worry too much about that, except - do not delete it (I'll come back to this later).
It's what is listed in iTunes that matters. Basically, iTunes is a database, that keeps a list of all the music that you have "told it about" (added to iTunes) and knows where it was located when you added it. So providing that iTunes itself lists and plays the songs, a Sync with the iPod should be okay.
Note my comment about playing the songs. As I previously stated, iTunes keeps a record of the location of the music file when you added it to iTunes. But if the file is subsequently moved, renamed or deleted (or in your case, not copied onto the new computer*), iTunes will not be able to find that file when it needs it. The result is that when you try to play such a song, an exclamation mark appears next to the song title and it does not play. It also cannot be added to an iPod.
Hopefully, you already know whether the songs can be played in your iTunes Library (I'm sure you don't want to check each and every one now). But if you do have any songs with exclamation marks next to the title, you need to remedy that before your Sync.
Once you are happy that your iTunes Library is sound, it looks as though you will be ready to Sync the iPod with it. It will probably take a while and sometimes iTunes can struggle to put everything onto an iPod in one Sync. Your Library may be borderline, but for large libraries, it is recommended to Sync a bit at a time. This can be achieved by choosing to Sync selected playlists, artists, albums and genres and selecting just a few each time. The option is on the Device/Settings/Music pane - see below.

This screenshot is looking at the iPod's settings for music. If you select Sync Music > selected playlists, artists, albums and genres in point (3.), then the panels in (4.) appear and the best option is to choose a few genres each time. At the next Sync, choose another few genres to add to the ones already on the iPod. Keep doing this until everything is on your iPod (assuming that every song has a genre allocated to it, which it should).
Finally, the Previous iTunes Libraries folder. The folder will have two important things in it:
- back ups of the database as it was at an earlier time. The best recommendation is don't touch it, just let iTunes manage this (unless there is a specific reason to change anything)
- some of your music (as noted below). In theory, all your music should be in one iTunes Media folder, but on my computer, the Previous iTunes Libraries folder also contains some of albums. I'm not clear why this should be so, but the folder has a sub-folder in it named iTunes Media and a further sub-folder named Music, which has several albums in it, that are a part of my Library.
So the golden rule is - do not delete, move or rename the Previous iTunes Libraries folder. But do remember to copy it to your next computer.
So where is all your music located?
The location of music can vary, according to several different past events. Basically, your music could be in any and all of the following (as mine is):
- Music/iTunes/iTunes Media/Automatically add to iTunes/...
- Music/iTunes/iTunes Music/...
- Music/iTunes/iTunes Previous Libraries/iTunes Media/Music/...
... and the ones that everyone seems to overlook - that digital music purchased from somewhere other than iTunes Store:
- Music/Amazon MP3/...
- Music/Purchased MP3/...
* Additional text added by author after initial post