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iPod won't sync with iTunes

I recently moved all of my music onto an external hard drive, but now when I plug in my iPod, it won't sync with iTunes. iTunes recognizes my iPod just fine, but no matter how many times I click the Sync button, they don't sync up. I've bought new songs in iTunes and they're not syncing to my iPod, made new playlists, etc. How can I get both of them to match up again? Why isn't it syncing? Can anyone help me out?


(I'm using iTunes 11 on Windows Vista, with an old style iPod)

iPod classic, Windows Vista

Posted on Mar 20, 2013 6:27 PM

Reply
49 replies

Jan 17, 2016 4:57 PM in response to Mark Harrigan

Are you able to play your songs in iTunes on the computer?


If you used a file manager to move the song files (outside of iTunes), iTunes may have lost track of where your song files are located. The iTunes Media folder location setting in iTunes preferences Advanced pane is for new media going forward. iTunes expects previously existing media to be where they were previously located, unless you let iTunes move the media files to a new location.


For future reference, this is how to tell iTunes to move its media files to a new location. This is useful, if you want to put your iTunes Media folder on an external drive (or a secondary internal drive). Create an empty iTunes Media folder at the desired new location. In iTunes preferences Advanced pane, point the iTunes Media folder location to that new iTunes Media folder. The TWO checkboxes for Keep iTunes Media folder organized AND Copy files to iTunes Media folder when adding to library should checked. Then, from the menu bar, File -> Library -> Organized Library -> Consolidate Files (checkmark box). This command tells iTunes to copy all of its media files, from wherever they are currently located, and organize them into the designated iTunes Media folder. Because iTunes copied the media files to new location, iTunes does not lose track of where the media files are located.

Let me know if you can (or cannot) play your songs in iTunes. If iTunes has lost track of location for its song files, you may see an exclamation point symbol next to song in iTunes. If iTunes cannot find its song files, iTunes cannot sync your iPod with those songs, and iTunes will remove those songs from the iPod (if you are using automatic syncing).

Mar 20, 2013 7:51 PM in response to heykelley

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.

Jul 4, 2013 5:14 AM in response to Kenichi Watanabe

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

Jul 4, 2013 11:43 AM in response to FrancescaO

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.

Aug 12, 2013 10:11 AM in response to Kenichi Watanabe

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

Aug 12, 2013 10:37 AM in response to shkubo

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

Aug 12, 2013 4:50 PM in response to Kenichi Watanabe

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.

Aug 12, 2013 7:56 PM in response to chrissiejo

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).

Mar 5, 2014 12:53 PM in response to Kenichi Watanabe

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?

iPod won't sync with iTunes

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