iPod won't sync with iTunes

Hi Kenichi,

Thanks for your amazing information and support with these ipod issues. I am having problems with syncing my ipod also. It it a classic and has been very well behaved forever- I have always manually updated files but this week after a manual update it went into some sync motions by itself after which the contents of the ipod were wiped. I have restored it a number of times but it is not syncing and have now put it in disk mode and gone through the mac disk utility- using verify, repair and erase- however all of these functions have brought up errors. I am wondering if my ipod hard disk has given up on life? Any suggestions are very gratefully received.

Thank you

I have restored it a number of times but it is not syncing

Does it go through the Restore process without error? If it does, (after the Restore) did you try to add songs manually or did you set up automatic syncing? Either way, what happens when you try to indicate "not syncing"?

What specific "errors" occur in Disk Utility, when you try to use the Verify and Repair command, and when you try to do an Erase?

Which "classic" iPod model do you have?

Hi Kenichi,

Thanks again for your reply and knowledge. I am not sure what model I have actually it is a classic 120gb click wheel that requested that my mac had at least OSX v10.4.11 when I got it. In running through the sequence of restoring in iTunes, verifying and repairing using disk utility I am now just getting the disk cannot be unmounted from disk repair and iTunes restore, disk verify believes there is a minor error in the volume header, and follows by saying the volume is corrupt and needs to be repaired, this followed with another unmount msg (I am aware now the ipod was not in disk mode at the time - so will try in this mode again now).

Any suggestions are appreciated....

Thank you

A 120GB iPod is a 7th gen classic.

http://www.everymac.com/systems/apple/ipod/specs/ipod-classic-late-2008-2g-specs .html

The error message about not being able to unmount the iPod's disk can happen, even if there is no problem with the iPod. It can mean that a "process" running on the Mac is accessing the iPod's disk for some reason. If iTunes is running, you should quit iTunes when trying to do a Repair in Disk Utility. If you quit all other obvious applications, and you still get that error message, you should simply restart your Mac, then immediately run Disk Utility and use the Repair command. Or use Restore in iTunes, if that's what you need to do.

If you do a Restore again, try manually adding a few songs to the iPod. It should work properly after doing a Restore.

Hi there again Kenichi-

Thanks again for your advice. I have tried the a cycle of repair and erase in disk utility followed by restore in itunes for the past few days but sadly to no avail. A few times things appeared to go better and I got as far as manually dropping a few songs onto the ipod- but when ejected it has no music on it.

Disk utility verify reports that the volume header needs minor repair and that the volume is corrupt; Repair says it can't repair the disk; Erase runs quickly and fine; iTunes restore goes through the process and at times I can drag and drop files onto the iPod - sometimes it says it can't sync (the sync is set to manual) other times iTunes freezes, each time on ejecting the ipod it is empty. Any further suggestions would be so gratefully accepted. Would it help to re-install itunes?

Thanks so much,
Helen

I have what sounds to me like the same problem as the user 'includemusic' above

I have an ipod Classic 6th/7th Gen (120gb, so still not exactly sure...) and today tried syncing to itunes 12.0.1 after years of hassle free use. itunes is now crashing, causing errors, partially syncing in both auto and manual transfer settings and is generally dysfunctional. I resorted to manually dragging and dropping a few albums at a time and that has been partially successful (woohoo I now have about 10 albums loaded out of my entire library this way...) but it has taken me all day to achieve this.

I've restored the ipod about 5 times and I've uninstalled and reinstalled itunes 3 times. I've tried all the various suggestions online. Still I keep coming up with a variety of 'unknown error' messages; 69, 53, 163 etc, freezes etc.

I am loathe to buy a new device when the device is fine and I'm p*ssed off with Apple for releasing a new version of itunes when there are still so many people using older versions of their devices - it comes across as cynical marketeering that requires us all to buy the latest hardware to keep pace with the software....

Please help!

ipod 6/7 gen 120gb

PC Windows 8

itunes 12.0.1

I have what sounds to me like the same problem as the user 'includemusic' above

I have an ipod Classic 6th/7th Gen (120gb, so still not exactly sure...) and today tried syncing to itunes 12.0.1 after years of hassle free use. itunes is now crashing, causing errors, partially syncing in both auto and manual transfer settings and is generally dysfunctional. I resorted to manually dragging and dropping a few albums at a time and that has been partially successful (woohoo I now have about 10 albums loaded out of my entire library this way...) but it has taken me all day to achieve this.

I've restored the ipod about 5 times and I've uninstalled and reinstalled itunes 3 times. I've tried all the various suggestions online. Still I keep coming up with a variety of 'unknown error' messages; 69, 53, 163 etc, freezes etc.

I am loathe to buy a new device when the device is fine and I'm p*ssed off with Apple for releasing a new version of itunes when there are still so many people using older versions of their devices - it comes across as cynical marketeering that requires us all to buy the latest hardware to keep pace with the software....

Please help!

ipod 6/7 gen 120gb

PC Windows 8

itunes 12.0.1

Hi, I don't know if you still answer these but my ipod nano 5th gen won't sync with iTunes, it doesn't even recognise it. The ipod knows it's plugged in and will charge but won't sync. It's a macbook pro if that helps (the one that was Snow Leopard but has been updated to Maverick). It always used to sync automatically but it wouldn't do it so I went to File > Devices and all of the options are in grey.

Not syncing automatically may mean the iPod got set to Manually manage music and videos somehow. So connecting it to iTunes (or clicking Sync) does not sync new content; iTunes and your iPod are expecting you to load content manually...

However, if the iPod does not appear in iTunes when you connect it, that is a problem. Watch the iPod's screen when you connect it. If you get the battery status symbol, or your iPod's home screen, that means your iPod is getting power, but it does not have a data connection with the Mac (the iPod's "disk" is not mounted). If it says something like "connecting" or "do not disconnect," that means there is a data connection.

What does the iPod's screen say or do initially, when you connect it to your Mac (have iTunes already running)? That answer to this question determines the next troubleshooting steps...

so I went to File > Devices and all of the options are in grey.

That is expected. That command applies to the device that is currently selected in iTunes. If no device is currently selected in iTunes, that menu bar command is greyed out. Since you do not have your iPod selected in iTunes, that is why that command is greyed out.

Thanks for replying so fast, how do I change that manually manage music setting? I couldn't see it in the ipod device menu, is it on itunes instead?

I don't think it's appearing in itunes but maybe I'm just looking in the wrong places, I haven't used itunes that much since that update that ages ago that made everything look really different so I'm not used to the layout.

All it does is put a lightning bolt inside the battery symbol in the top right corner and once it's fully charged it's a big battery in the middle of the screen, those are the only 2 things it does, it doesn't say anything about syncing or not to disconnect (it used to but not anymore)

If the iPod does not appear in iTunes when you connect it, you cannot change any of its sync-related settings. If you can see and select the iPod in iTunes, the "manually manage" setting is on the iPod's Summary settings screen (in iTunes); what you see after selecting an iPod in iTunes. Since you only get the iPod's home screen or the battery status symbol (on the iPod) when you connect it to the Mac's USB, it's like you are connecting it to a USB power (wall) adapter. It's acting like the connection is only for power. There is no data connection.

If you have not already, be sure to try doing a Reset on the iPod (to restart it)

Reset your iPod - Apple Support

Then connect it to Mac running iTunes. If that does not help, try putting iPod into Disk Mode

Putting iPod into Disk Mode - Apple Support

Then connect it to Mac running iTunes. iTunes may prompt you to do a Restore, which would be good news since the iPod is now being recognized. Note: Doing a Restore erases the iPod, and you'll need to re-sync it from your Mac's iTunes library.

If those steps do not help, you can reply back for some other things to try...

Hello Kenichi,

To give a bit of background: I actually have a new iPod, but this topic is the only one I've found that actually gives a working solution to the not syncing issue. I was updating my Macbook Pro to Yosemite and there was an error and it wiped my hard drive. I hadn't backed up my music in a while (and don't necessarily have the CDs I ripped some of my music from anymore), so I used a third party software to get my music from my iPod to my iTunes library. No problems there. To do that I had to check off the prevent devices from syncing automatically option in preferences. I didn't check off the manually manage option in the summary section, because I like the automatic syncing. I unchecked the prevent auto syncing, so that I could sync my fully completed library and not lose any music. I can't get the sync button to work; not even through the File -> Devices -> Sync option.

You recommended checking off the Sync Music option under the Music tab when looking at the iPod. Like the person before me, it drastically reduces the number of songs syncing to my iPod. All of the music I currently have on my iPod is in my library now, so is it only syncing purchased songs? I don't understand how to get all the music from my library to sync onto the iPod if the Sync Music option doesn't recognize songs despite clicking Entire Music Library. (Would it take two syncs to get the entire library? First one would be the reduced number and then the second syncs the songs it didn't recognize? Would syncing via Sync Music erase anything in my library or just erase the iPod music?)

but this topic is the only one I've found that actually gives a working solution to the not syncing issue.

As an FYI for future questions, you can just create a new topic. That's how this forum is designed to operate, when asking a question. But it's good to read existing topics... 🙂

All of the music I currently have on my iPod is in my library now, so is it only syncing purchased songs?

If all of your songs are in your iTunes library on your computer, you can try a few things including a Restore. And NO, purchased songs are treated the same as other songs for iPod syncing, if you have authorized your computer for the Apple ID used to purchase. If the computer is not authorized for the Apple ID used for purchase, old songs purchased from the iTunes Store may not sync due to DRM (copy protection), and you'll get an error message. More recent iTunes Store song purchases no longer use technical DRM. And there should not be a case where ONLY purchased songs sync using automatic syncing, if you are setting it to sync the entire music library.

You recommended checking off the Sync Music option under the Music tab when looking at the iPod.

That's not just a "recommendation." That is the one and only way to set up automatic syncing. And with iTunes 12, it is no longer accessed on the "Music tab." In iTunes 12, select the iPod in iTunes. You initially see the iPod's Summary settings screen. In the sidebar (along left side of window), click Music under Settings. To the right, you see the iPod's Music settings screen (what was previously the "tab"), where the Sync Music checkbox and other music sync settings are located. Assuming you are using the latest iTunes version, is that where you are looking?

If you check the box for Sync Music, select the option to sync Entire music library, and Apply the change, you should get your entire music library on the iPod (assuming your iPod has the capacity to hold your entire music library). NOTE: Be sure to look at the checkbox on the iPod's Summary settings screen for Sync only checked items. If that box is checked, and you have songs that are unchecked in your music library, only the checked songs will sync.

Pick one of the songs that does not currently sync. Make sure you can play it in iTunes. Do this with the iPod NOT connected, in case iTunes is somehow accessing the song's file from the iPod. If you can play it in iTunes, iTunes knows were the song's file is located on your computer's drive. If iTunes has lost track of the locations of some song files, then those songs will not play in iTunes, and iTunes will not sync them to the iPod.

Otherwise, since you have ALL of your songs in your iTunes library, you may want to do a Restore on the iPod using iTunes.

Restoring iPod to factory settings - Apple Support

This erases the iPod, reinstalls its software, and sets it to default setting. You can then sync the empty iPod from your iTunes library, with the Sync Music / Entire music library setup. All songs should sync.

I apologize for not making a new thread. I was checking through all the iPod categories and when I stumbled upon this, I was very excited. I thought making a new topic be considered a duplicate discussion and that I would be redirected here.

I used the Sync Music option under the iPod's Music settings and it's working perfectly! Turns out part of my problem was that iTunes no longer recognized that my laptop was authorized, so that's why I wasn't seeing all of my songs when looking at the Sync Entire Library option. Once that was fixed, everything went smoothly.

Thank you so much for your help and explanations!

Glad to hear it was something simple and easy to fix. 🙂