IPod Won't Sync Particular Song

I purchased five songs from iTunes the other day and one of them will not sync to my iPod. The same thing happened earlier this summer and I tried what the tech support person suggested, but it didn't work. I thought I'd try my luck with the song again, but it still wouldn't sync to my iPod because of a :50 error (I think that was it). Has anyone else had this problem with an iTunes song? Any suggestions on how to get it to sync? I've tried restoring my iPod and that doesn't help. Thanks!

Does it play in iTunes?
Is the format or source of the song different that ones that do sync?

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Ipod won't sync certain songs after update to 5.1.1

I updated my ipod touch to version 5.1.1. This included the addition of icloud to my system. Since I have updated it, my ipod won't add certain songs from my itunes. It's really weird how it just randomly selected songs to download. I have songs in itunes that I purchased, as well as songs I imported from CD's. Every song shows up on my ipod song list, however most are "gray" and won't allow me to select them to play. (like they are not downloaded or something). I have retored my ipod three times to see if that will allow all the songs to play on my ipod and it won't work. Everytime I try to sync my ipod the fist song that tries to sync says "The file wasn't synced to the ipod because it cannot be read or written"......I have tried removing multiple songs and still get this message for every song. I did figure out that you can open the itunes store through the ipod and select "purchased". You can then view songs that "aren't on the ipod" and manually download each individual song to the ipod, however, not only is this a pain in the *** and going to take forever since I have 1000+ songs and tv shows, but this still won't get all my own music added from CD's to my ipod. HELP! Any tips or solutions!! ( Also, I am a Mac user if that makes a difference)

After over TWO HOURS on the phone with apple support I still had no solution. There were several songs that would freeze up my itunes, then I got the message "blah blah song" couldn't be transfered to the ipod because the file was unable to be read or written. The tech and I came up with the solution to just delete every song that came up on. In the end, I had to individually add EVERY SINGLE SONG to my ipod one at a time. If an error popped up I just deleted that song and made a note of it. I had no issues with the songs I imported from CD's, only the songs purchased off itunes. The tech never could figure out why. We rebooted, wiped clean, reset, anything...you name it we tried. We even moved everything to another computer to see if it was a computer issue, then we wiped my husband's ipod touch to see if it was a hardware issue on my ipod. NOTHING. This finally worked even though it took all day. Everything seems okay now, we will see the next time I add songs. I did lose ALL my photos and videos taken with the ipod. :/ That really ***** because I have a 1 year old who's entire first year was on that stupid thing. What a waste of a day.

My iPod won't sync purchased songs.

I get my music from both CD's and the iTunes store, but when i tried to sync my iPod yesterday it deleted all the songs i purchased from iTunes but the CD songs still remained. All my songs still show up in my music library on my computer but won't sync onto my iPod. What am i doing wrong?
also, this all happened right after i had to reinstall iTunes for some unknown reason.

i'm having this same problem, any ideas?

160 GB iPod Won't Sync All Songs From iTunes

I have a 160 GB iPod and barring the normal song-skipping issues everyone seems to have, I've had no problems out of it. That is until a couple of days ago. I would attempt to listen to a song and it would skip to the next one during the middle of it. It would run sluggishly, skip nearly every song, and at times, freeze. So I decided to exercise the restore option. After that, when I tried to sync it to my library, it only synced 330 (out of 14,000 plus)songs, all of them artists starting with A. I've tried rebooting and restoring the iPod to no avail. I even did a system restore for my entire computer. Nothing works; it insists on giving me only a fraction of my music library. Any suggestions?

*Hard Drive Diagnostics*
Take your iPod and place your right thumb on the centre SELECT button and your left on the top MENU button. Press down both thumbs for about 6 seconds until your iPod reboots. Immediately move your left thumb around to the rewind button |<< on the left and hold this down together with SELECT for a further 6 seconds. Your iPod should now switch into Diagnostic Boot mode. Press MENU for *Manual Test*, then select *IO > HardDrive > HDSMARTData* to reveal your stats. For comparison here are mine for my 2 year old 6th Generation Classic:
Retracts: 889
Reallocs: 12
Pending Sectors: 0
PowerOn Hours: 2202
Start/Stops: 894
Temp: Current 24c
Temp: Min 10c
Temp: Max 50c
Take a note of your results. When finished press *SELECT & MENU* for 6 seconds to reset the iPod again.
With modern disc drives sectors are no longer marked bad by a disc scan, if the SMART firmware detects a sector it has trouble accessing it will attempt to invisibly reallocate it to a spare area of the disc.
Note that I've only 12 remapped sectors and none pending. To help explain what the numbers mean here is an extract from the Wikipedia S.M.A.R.T. article:
*Reallocated Sectors Count*
Count of reallocated sectors. When the hard drive finds a read/write/verification error, it marks this sector as "reallocated" and transfers data to a special reserved area (spare area). This process is also known as remapping, and "reallocated" sectors are called remaps. This is why, on modern hard disks, "bad blocks" cannot be found while testing the surface – all bad blocks are hidden in reallocated sectors. However, as the number of reallocated sectors increases, the read/write speed tends to decrease. The raw value normally represents a count of the number of bad sectors that have been found and remapped. Thus, the higher the attribute value, the more sectors the drive has had to reallocate.
*Pending sector count*
Number of "unstable" sectors (waiting to be remapped, because of read errors). If an unstable sector is subsequently written or read successfully, this value is decreased and the sector is not remapped. Read errors on a sector will not remap the sector (since it might be readable later); instead, the drive firmware remembers that the sector needs to be remapped, and remaps it the next time it's written.
Large numbers of Reallocs or Pending Sectors would suggest your drive is failing and that you may need to repair or replace your iPod. Check your stats after another attempt to update your iPod. If the numbers increase that again points to hard drive failure. While it won't be good news at least you'll know it isn't some random software problem and you can decide what to do next.
tt2

30 GB Video iPOD won't sync purchased songs from iTUNES.

Previously, on the same computer, I have synced purchased songs from my Itunes library to my iPOD. Now, suddenly, an error message says that I'm not authorized to do so. I use my computer in two countries, the US and Taiwan, and wonder if this has anything to do with the problem. I've already restored the Ipod and reloaded all the songs. The purchased songs still appear in my library but will not sync.

Have you tried Deauthorizing then Authorizing your computer through the Store menu in iTunes?

My iPod won't sync some songs from iTunes?

It is't on manually manage music and it used to sync every song but now it won't sync any at all?

Of course it will not sync at all. You have it set to manually manage music.
You can manually manage ( drag and drop) OR sync, but NOT both.

Ipod won't sync with songs on Itunes

I just recently bought a laptop and it has Windows Vista 64 bit (Home Premium). I was able to sync the Ipod (40GB 4th Gen) with the laptop as far as transferring purchases. But I can't get the Ipod to sync as far as taking songs from Itunes and putting it onto the Ipod. I tried manual syncing but that's not working either. Now when I try to go back to having Itunes and Ipod automatically syncing and hit apply it still goes back to manual syncing. Please help.

Thank-you. I figured it out myself. I realized that since it's set to have the ipod manually synced that when I have songs I want to go from Itunes onto the ipod I have to click and drag the song over the top of where it says device ipod on the left hand side.

My iPod won't sync any songs or videos that are in the iTunes Library.

I have an iPod classic [80 GB] and it does not, recently since I updated the iTunes to the newest version, for whatever reason iTunes will not be able to sync music or any of the music videos I have giving me a error message [Like rite now it told me: Attempting to copy the disk "RADKE777" -which is the name of my device- Failed. An error has occured (-69)] then iTunes will freeze completely and I cannot do anything with it.
What does that mean? It was just working recently.. the only thing that I have done differently, like I said, was update iTunes.. I'm not really sure as to what to do. If ANYONE can help me I'd appreciate it! >.<

It could be an indication or a damaged or dying hard drive. I would recommend doing a disk diagnostic on the iPod's HD using the instructions given by turingtest2 in this older thread. He also covers what the resulting numbers indicate.
https://discussions.apple.com/thread/3784647?start=0&tstart=0
If necessary, post the resultings numbers and we can verify what the next steps to take.
B-rock

IPod won't sync purchased songs or show album art

I purchased a brand new 80 gig iPod yesterday, and I'm having slight problems with it. When I plugged it in, it told me that my iPod software was too old and couldn't transfer some of my songs (which ended up being the songs I downloaded from the store over the past several years). I checked to see if about an update, but the iPod menu says the software is up to date. I'm wondering if there is a setting I need to fix. Interestingly, it says my iPod is formated for Windows, but I'm using a Mac and did not have a choice between a Mac or PC. If this is an issue, can someone help me format it for Mac?
Also, it's a slight issue, but even with album art downloaded from online store, none will show up on my iPod. Why is this, and how do I fix it?

Hi.
Follow these instructions. If no luck then please post back.
http://www.apple.com/support/ipod/five_rs/
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I have one of the original IPOD's and just tried adding a bunch of songs, (200) and now that they're on my computer my ipod won't sync as it now says i need about 8.45 more gb. any thoughts on this?

I have one of the oriignal IPOD's circo 2006. I've got about 150 tunes on it which has been fine but today tried to add another 200 or so and was advised I need about 848 MB to load them. Is there any solution. I have 2 playlists. One with the original 150 tunes and one with the addiitional 200 tunes. Thoughts as now my IPOD won't sync at all and I don't want to delete any of the songs if I don't have to.

How much storage on the IPOD - I have one that has 60GB on it. Also have an IPOD shuffle that held less songs.
As your IPOD does not have enough storage for all of your songs, you have to create a list to sync to it that does not exceed the storage size.
For instance my IPOD shuffle had its only list of songs that did not exceed storage.
The IPOD gets them all because I only loaded the songs from my CDs that I really liked into ITUNES - leaving out the ones I skipped over.

ITunes opened another library, now iPod won't sync

I have a Dell laptop with iTunes installed on it, and an iPod touch 5th gen. with the most recent software update. But Windows just recently had an update and so I updated the software of my laptop and iTunes continued to work fine. But just a few days ago I turn my computer off and the the next day turn it back on in an attempt to sync my iPod but when I plug my iPod into the computer before I open iTunes, the iPod makes it open automatically and the terms and services agreement pops up. And I'm thinking why is this here again b/c I haven't updated iTunes or anything but i know it won't open unless I agree, so I agree. (But oddly, I think it said "save" instead.) So I click whatever it says (save or agree, I can't really remember) and iTunes opens but it's an older version of my library.
All my most recent songs are gone, and my iPod won't sync b/c it's not being recognized by iTunes. (When I started syncing this iPod with this computer I had to make it start over completely and erase all data to make it forget my old computer.) But now that it's the wrong iTunes library, it won't sync anymore. :/
I don't want to have to erase all my data again...But why did it do this? I've tried to go through and make it open the other libraries (holding shift and clicking on iTunes to tell it to open another library), but I can't find the most recent one. I'm assuming the library is still there on the computer but I can't find it, but I didn't delete anything and iTunes never warned me of any issues, so the library has to still be on the computer some where. I tried closing iTunes and reopening it but that didn't work, neither did turning the computer off and turning it back on.
How can I fix it?
Sidenote: all my songs were consolidated to that particular library. (If that matters.) And my iPod still seems to be working fine.

I had the same problem on my iphone 5s, and this fixed it. http://support.apple.com/kb/TS5335

My ipod won't sync any of the music i downloaded and says that iTunes can't backup the Ipod because a session couldn't be started with the Ipod how do i fix this

My ipod won't sync any thing in my iTunes library it always stop as soon as it starts backingup the Ipod a message appears that says iTunes cannot backup the Ipod "my Ipod" because a session couldn't be started withthe Ipod how do i fix this problem?
This is exactly what the message says: iTunes could not back up the iPod "austins ipod" because a session could not be started with the iPod.

Try connecting your ipod to another computer and sync only 1 file or song just for isolation purpose only to see if it'll sync.
If still not syncing, then porbably you may have a bad iOS installed in iPod which is hard to see if it has a problem because you said nothing's wrong with iPod. I just saying is, it MIGHT have a bad iOS.
If you are unable to do a restore, put your ipod in DFU mode, then connect to iTunes and iTunes will detect your ipod in restore mode. Press shift key (PC keyboard) then click the restore button on iTunes. I hope you have your copy of IPSW file for restoration purposes.

5th Gen iPods won't sync

my 60 & 80 gig iPods won't sync to iTunes. When I connect them, they appear in iTunes, but I cannot add or delete music and several of the playlists don't show up on the iPod. My newer 120 gig iPods work fine. This started on 8-8-10. I am running the current version of iTunes.

I've been having the same problem ever since I upgraded to iTunes 9. Before the update I never had any issues syncing new songs or playlists. I have purchased several new albums and haven't been able to get them synced to my iPod. When I plug in my iPod I get the syncing message and the "Do Not Disconnect" message shows up on my iPod for about 30 seconds to a minute, but when it finishes nothing has been added and the storage amounts haven't changed.

IPod Won't Sync After Moving Music to New Computer

With the help of someone here, I moved my iTunes Library from my old computer to my new one. It didn't work exactly like it was supposed to. All of my music is on my new computer and in my iTunes library, but my playlists, counts etc. are gone. Whatever - I'll deal. Now, though, my iPod won't sync with my new computer (which I did authorized). The "Do Not Disconnect" sign never goes away after I connect my iPod. Thoughts?

*I'm afraid to plug in my iPod in fear of it erasing my playlists...*
If your iPod is set to update automatically you need to take care connecting to a different iTunes. You'll get a message that it is linked to a different library and asking if you want to link to this one and replace all your songs etc, press "Cancel". Pressing "Erase and Sync" will irretrievably remove all the songs from your iPod. When your iPod appears in the iTunes source list change the update setting to manual, that will let you use our iPod without the risk of accidentally erasing it. Check the "manually manage music and videos" box in Summary then press the Apply button: Managing content manually on iPod
You can also use a keyboard command to prevent your iPod auto-syncing with iTunes. While connecting the iPod to the computer on Windows with iTunes 7.3 or later installed hold down the Shift + Ctrl keys together. This will stop the iPod from auto-syncing with iTunes and the iPod will appear in the source list. Wait until you are sure the iPod has mounted, and that it will not auto sync and then you can let the keys go. This may take between 20 to 30 seconds depending on your computer: iTunes - Keyboard Shortcuts for Windows
*but should I plug it in to restore playlists??*
Your playlists won't be restored by simply connecting your iPod to iTunes.

My iPod won't sync; how do I fix this?

My iPod won't sync any of my music. It says there is a disk error. Is this a hardware issue or something else? What should I do?

Try connecting your ipod to another computer and sync only 1 file or song just for isolation purpose only to see if it'll sync.
If still not syncing, then porbably you may have a bad iOS installed in iPod which is hard to see if it has a problem because you said nothing's wrong with iPod. I just saying is, it MIGHT have a bad iOS.
If you are unable to do a restore, put your ipod in DFU mode, then connect to iTunes and iTunes will detect your ipod in restore mode. Press shift key (PC keyboard) then click the restore button on iTunes. I hope you have your copy of IPSW file for restoration purposes.

IPod Won't Sync Particular Song

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