Q: iPod won't sync with iTunes

If you did the move of your music to an external drive using iTunes, through the command in

iTunes menu bar -> File -> Library

iTunes keeps track of the new location for all of you song (and other media) files.  As long as you can play those songs in iTunes, the move to the external drive should not be causing a syncing problem with the iPod.

Did you set up the Music tab for the iPod?  Select the iPod in iTunes.  Near the top of the iTunes window, there is a row of "tabs" (they look like buttons in the latest iTunes) that starts with Summary.  Click on Music there.  This tab is where you tell iTumes how to sync your music library to the iPod.  Make sure Sync Music is checked.  Below that, if your entire music library will fit on the iPod, you can select Entire music library; any change you make to your music library will sync to the iPod.  Otherwise, you need to make a selection of songs based on Selected playlists, artists, albums, and genres. 

If you added new songs to the library, or created new playlists, they need to be included in the selection on the Music tab.  If they are not part of the selection, they will not sync to the iPod no matter how many times you click the Sync button.

Once you have set up the Music tab, click Apply to sync the selection to the iPod.  Going forward, any changes made in the music library that are related to the selection on the Music tab will sync automatically to the iPod, when it is connected or when you click the Sync button.

Thank you. After hours of looking this was the best answer across the board.

Hi Kenichi,

I'm having this same problem! However when I click on 'Sync Music,' the bar on the bottom showing the amount of data on my iPod shrinks right down from 818 songs to 381. I can either choose to Revert or Apply, and I don't know what to do. I think the loss of 500-odd songs would be music I've uploaded from CD's in the past.

So I don't know that if I click Apply, and the CD music will be lost, I can re-upload the CD music and it will sync? Will it let me do that? If I do all of this, will it then sync new downloads from the Store?

Any help you can give me would be appreciated Thank you!

Me

If the iPod was NOT previously set to do automatic syncing (the Sync Music checkbox was NOT checked before), you were probably loading songs on the iPod manually, by dragging and dropping songs onto the iPod in iTunes.  When you use the manual method, once you put a song on the iPod, you can delete that song from your iTunes library.  Therefore, it is possible that by setting up automatic syncing now, you will lose songs.  Any song that is currently on the iPod that is NOT currently in your iTunes library will be lost.

If those lost songs are from music CDs, you can re-rip those CDs to get those lost songs back into your iTunes library.  Then, you can set up the Music tab to include those songs in your automatic syncing.

As I described in the reply to the original poster, you use the iPod's Music tab to make your selection of songs that you want iTunes to automatically sync to the iPod.  It does not matter if the songs you select are from music CDs or from the iTunes Store, or from any other source (or any combination).

One convenient way to set this up is to create a new regular playlist in iTunes.  Call it something like "iPod Songs."  From your iTunes music library, add ALL the songs you want on the iPod to that playlist.  Then, go the iPod's Music tab in iTunes, and under Playlists, find and checkmark that new playlist. 

When you click Apply, all songs on that playlist sync to the iPod, replacing its current content.  Going forward, when you want to change the music on the iPod, just update that playlist by adding or removing songs.  The next time iTunes syncs the iPod, those same changes are made automatically to the iPod.

I'm having problem syncing my ipod which I just bought.  I've followed the instructions, one was to connect it to the computer after I have opened itunes which I did.  It said it would automatically syn but it didn't. nI clicked on devices and I clicked on sync and I did and it says it has synced but when I check it hasn't.  What's happening?

Sakae

You probably need to set up automatic syncing, to tell iTunes what to sync to the shuffle.  Otherwise, clicking on the Sync button syncs nothing.  How to do so is provided in the first reply to the original topic creator (the one with green checkmark), starting with Did you set up the Music tab for the iPod?

This document also provides information about syncing music to

http://support.apple.com/kb/ht1351

Just encountered this issue today it's frustrating. My ipod used to auto sync when connected. Today when I puchased tunes they did not sync even though the box on left is checked. I did the click on device, click on music button and that box that says Sync music in upper left corner .  When I did this  message box aked if I was "sure I wanted to delete" the playlist from ipod and continue sync....I have never seen this before and don't think I want to delete music. Also tried the sync button down by the space used bar too and nothing happened. Your previous answer was very clear to someone like me who not tech savvy....but that delete message me threw off. 

If that Sync Music checkbox was not already checked (on the iPod's Music screen), your iPod somehow got set to the Manually manage music setting. You can check on the iPod's Summary screen in iTunes, to see if that Manually manage music checkbox is checked.  If it is, iTunes is not going to add new songs to the iPod automatically.

(It may have happened if your iPod was previously set to sync the entire iTunes music library, and recently, the size of your iTunes music library exceeded the storage capacity of your iPod.)

If every song on the iPod right now is in your iTunes library, you don't have to worry about that warning.  That is a general warning, indended for people who have been using the manual method to load the iPod, and may have songs on the iPod that are not in their current iTunes library.  iTunes may remove songs from the iPod (when setting up automatic syncing), but they are not deleted from your iTunes library.  So if all songs on the iPod are in your iTunes library, iTunes will just sync them back to the iPod (based on how you set up the iPod's Music screen). 

Thanks so much!

Thanks Kenichi.  I hadn't synced my ipod for over a year and didn't realise I had to tick a box in the music tab.

I'm having the same issue so “reset” it. I managed to back up my songs but now that my ipod returned to it’s factory settings, all the songs that were erased won’t re-sync. A window keeps popping up saying ” The ipod “RaeRae’s ipod” cannot be synced. You do not have the privileges to make these changes.”  and it also said I could not copy my disc ( my ipod ), apparently I "don’t have the privileges to make those changes" either.

I tried your suggestion but it didn't work.

Any other options or do I have to call tech support?

That sounds like a Windows-related error (assuming your OS is Windows), related to your user account and what it is allowed to do on the computer.  Take a look at this discussion thread and the advice with the yellow star next to it (the second one).

https://discussions.apple.com/message/19691479

Perfect!  This was exactly the issue with my iPod.  I had moved my music files from one drive to another.  When it asked me to sync with the new drive, everything worked.  Thanks!