Can't transfer music to ipod

Just want to confirm that this is a very early iPod that has a FireWire port in it, instead of the Dock Connector.

So your computer has a 6-pin (powered) FireWire port, is that correct?

If the above it true, you may need to use Restore on it, because you were using it back when Apple did not even have iTunes for Windows. Restore will install the latest version of the iPod's software, which is probably needed to make it compatible with iTunes.

If you don't want to lose the song files on the iPod, try using this method to transfer the songs files from the iPod your computer first.

http://lifehacker.com/software/ipod/how-to-copy-songs-from-your-ipod-to-your-pc- 105256.php

Actually, if you were using the iPod with MusicMatch, the songs may be stored more plainly on the iPod. Enable disk use on the iPod and open it using Windows Explorer. See if there are any obvious folders on the iPod where the song files are stored. If not, use the link above to make hidden files and folders visible.

That "2.3" software sounds like a 3rd gen iPod. It has a dock connector, touch (not click) wheel, and four round touch buttons that glow orange.

The 3rd gen iPod was designed to be connected using FireWire. If you are connecting it to a USB port using a USB Docking Cable, it may not work properly, and it will not charge while connected.

Do you have a FireWire connection, or are you using USB?

The buttons should glow at the same time the back light for the screen comes on.

It would not have come with a USB Docking Cable; it would have come with a FireWire docking cable. I don't think Apple even made USB docking cables at that time, since the first iPod to fully work with USB was the next model, the 4th gen iPod.

If you have the special docking cable that has both USB and FireWire, that is good. You should be connecting the USB end to the computer and the FireWire end to the power adapter. That is the only way to sync and charge your iPod at the same time, other than having a FireWire port on the computer and using FireWire to sync and charge.

Otherwise the battery discharges too rapidly.

So one problem with the iPod is that the battery is worn out. But the iPod should operate normally as long as it is connected and receiving power through the dock connector.

I can find my music files on the iPod using Windows Explorer. They seem to be jumbled up, not obviously in albums or playlists.

If you can see the music files on the iPod, that is good. Try the following.

Run iTunes. Go to iTunes preferences Advanced pane. Check BOTH the check boxes for +Keep iTunes Music folder organized+ and +Copy files to iTunes Music folder when adding to library+. The second checkbox, if you did not have it checked before, you can uncheck after this procedure. Also, note the location shown in +iTunes Music folder location+; that is where your music files from the iPod should end up.

With the iTunes window open, create a new playlist and name it Transfer (or whatever you want). Select that playlist in the iTunes sidebar. Open a Windows Explorer window and show the music files on the iPod. Select all the music files or select the folder(s) containing the music files, and drag them to the open iTunes window over the empty Transfer playlist listing. Drop the folder(s) or songs files onto the listing in the iTunes window. iTunes should add those songs to the Transfer playlist and your main Music library. At the same time, it will copy the music files to your designated +iTunes Music+ folder and organize/rename the files by artist and then by album. The reason you created the Transfer playlist is so that you can see all the added songs in one place, instead of scattered through your Music library listing.

Do a +Get Info+ on a few songs transferred from the iPod to make sure they are being accessed from your +iTunes Music+ folder. The path the song's file is in the Info window, on the Summary tab.

Unfortunately, there is no easy way to retrieve the playlist. You may be able to do it with a third party utility, but the one I know of that can retrieve playlists is not free.

http://www.zeleksoftware.com/liberator.htm

I guess you're suggesting that I copy all the music from my iPod back into iTunes so I can restore my iPod and not lose the music and its organization.

Yes. The organization in the iTunes library listing and in the +iTunes Music+ folder will be based on the tags in the music files (data embedded in the files such as song name, artist name, and album name).

after I restore, I can (hopefully) transfer all of my music back to the iPod.

Yes. If you use the sync setting, once you get all of your songs (the existing songs and the ones from the iPod) set up the way you want them in your iTunes Music library, including any playlists you may want to create, you sync your iPod to the iTunes library. Based on your sync settings, the iPod will mirror what's in your iTunes library. If you later add more songs and sync, the iPod will have the new songs. If you remove songs from the library and sync, the iPod will lose those songs.

You have the option to not use the sync setting; you will +manually manage music+. In this mode, you manually add songs and remove songs from the iPod using iTunes. You are not syncing to your library.

I also expect that I should add any music that was not previously on the iPod to the transfer file before transferring it back

There is no "transfer file." At any time, you can add new songs to your iTunes library and then sync the iPod. Based on your sync settings, the iPod will have the new songs after syncing. So it's an ongoing process, not something you have to do BEFORE anything else.

The assumption here is that after restoring, the iPod will behave better and allow me add back all of my music

Of course... If the iPod is not working, it's not working.

Why did it not transfer when I synced?

If the songs are in your iTunes library (they appear on the list in iTunes), and on the iPod's Music tab (in iTunes), it is set to +Sync music - All songs and playlists+, then the iPod should have the exact same songs after you do a Sync. Make sure it is not set to just sync +Selected playlists+.

So I found the same files on my computer in "My Music".

If you already had the song files on your computer, then trying to get them off the iPod was wasted effort.

For the music that did not transfer, try playing that same song in iTunes. Does it play in iTunes?

Not all of the music listed in my iTunes Music list shows up on the iPod music tab.

That statement does not make sense. The iPod's Music tab in iTunes (select iPod in the sidebar and go to the right side of the iTunes screen), does not contain a list of songs. It does contain a list of playlists, but if you have +Sync music - All songs and playlists+ selected, it will transfer all songs in your iTunes library. Well, all songs that have accessible files, that is; if a song's file was moved or removed, that song will not be playable in iTunes and it will not transfer to the iPod (because iTunes cannot locate the associated song file).

I think I see the disconnect here. You must be looking at Music under the iPod's name (in the sidebar). When I say Music tab, what I mean is:

Select the iPod's name in the sidebar under DEVICES.
Look over to the right on the iTunes window.
Toward the top of the window, you will see "tabs" starting with Summary.
Select the Music tab. On take tab, you set up how your music is synced.

If you want to have it sync everything that you see and can play in your main Music LIBRARY list, you need to set it to +Sync music - All songs and playlists.+ Then click the Apply button at the bottom right corner of the iTunes window.

On the iPod's Summary tab, is the checkbox for +Manually manage music+ checked or unchecked. If you want to sync, it needs to be unchecked.

Also, is the checkbox for +Sync only checked songs+ checked or unchecked? If should be unchecked.

If you made a change to either setting, you need to click on the Apply button.

But if the iPod can't see all those other albums for whatever reason, then they won't sync.

Do all of these albums appear in your main iTunes music library? If so, can you play those songs in iTunes. If so, and the settings mentioned above are unchecked, and the Music tab is set to +Sync music - All songs and playlists+, then whatever is in your iTunes library will be on your iPod after you sync (assuming the iPod has enough capacity to hold your entire iTunes library).