I have been experiencing the Error 69 in iTunes lately when syncing iPod. The full error message read “Attempting to copy to the disk failed. An unknown error occurred (-69)” which is not really that helpful if you ask me. I figured that this was some kind of transfer problem and decided to investigate it further.
I started the syncing again in iTunes and observed the songs that are synced with iPod. Error 69 appeared again of course but this time I memorized the last song that was synced and decided to remove it for now from the iPod and iTunes.
After that I restarted the syncing process and it went through without a problem. I’m not sure if this is the appropriate method of getting rid of ipod error 69 in iTunes but it has helped. I was fortunately able to rip the song again from CD and copy it back to my music library.
This time it would sync without difficulties which was a relief. I hate it when an album on my iPod or PC is missing a track.

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I’m getting error 69’s a lot more lately. I wonder if it’s tied to the newest version of itunes or my new ipod touch?
i hv the same problem… when i try to sync my ipod… it says.. Attempting to copy to the disk failed. An unknown error occurred (-69), can someone tell me what to do??????
should i format the ipod????? pls. help!
This problem can be fix in apple website but the way to fix it seem little bit hard on u guys, y dun u send it back to apple and tell them to fix it, that would be the best way. I got the same problem and on the next monday i;ll sent it to apple store they told me: “free to fix” so why dun u guy just try. =__=
I’m having the same problem but there are many songs it may or may not occur on. I went to the store and they told me to reset, then restore then they gave me a new one. I suppose I’ll try to watch for which trtacs have problems, but with 13000 tracks, it would take a few hours of watching that bar, pls it doesnt always show the current track being worked on.
Oy I don’t want a new ipod and some of the songs that this occurred on were songs I had before but accidentally deleted and needed to reload. If they worked the first time why would they be corrupt the second time. I think it could possibly be the new version because i was fine till i updated.
I do this but even when i uncheck all songs it still says this
also once i restore to factory settings theres still 30mb on my ipod, what is this???
Awesome, thanks!Personally i believe you are brilliant.
I had this problem with iTunes v1.3(WinXP SP3) & my 30GB iPod video(5th generation) despite using the ‘Restore’ option on iTunes. I eventually solved it by doing the following;
Click ‘OK’ to the error message “Attempting to copy to the disk failed. An unknown error occured (-69).”
Do NOT eject the iPod icon from the DEVICES pane but right click the iPod icon instead.
Select the ‘Reset Warnings’ option from the pop up menu.
Click ’sync’ and iTunes continues from where it left off loading your iPod hard drive and sycning some more.
If the error box appears again (it did for me several times) then repeat this procedure until eventually ‘iPod sync is complete – Okay to disconnect’.
Hope this works for you too. (30-Dec-2008)
this is great info, but duznt exactly help. the way you’re doing it will not tell u which file is corrupted, it will only have the ipod skip syncing the file, so that it wont be synced to the ipod. i also hypothesize that this corruption can spread, so if the file is left unchecked, more files may become corrupt
ma ipod duin this and i really wanna fix it but i dont have the reciept anymore
thank Rob so far its working ive done everything from restoring to reformating it!!!! Thanx a bunch
This worked for me
Click ‘OK’ to the error message “Attempting to copy to the disk failed. An unknown error occured (-69).”
Do NOT eject the iPod icon from the DEVICES pane but right click the iPod icon instead.
Select the ‘Reset Warnings’ option from the pop up menu.
Click ’sync’ and iTunes continues from where it left off loading your iPod hard drive and
Thanks
I tried that and it just freezes afterward.
Mine is the same as jess there is no option to do anything other than eject when you right click the icon in devices. Ipod has lost all its songs but will not speak to itunes to sync again
Thanks, Rob!! Your suggestion worked for me as well.
Listen to Rob, hes got the technique
Unfortunately whoever first started telling people that their files are bad and they need to delete it from the iPod is just wrong. Here’s how you REALLY fix it: Restore your ipod, making sure to place it in disk mode. Wait for the ipod to sync, and when it starts freezing on a song, rapidly tap or hold play/pause until it starts syncing again. Your iPod isn’t timed correctly with the computer and that’s that’s the reason for the error. pressing play will kick the iPod in the ass and make it line up with the process on your PC. You’re all welcome in advance.
moody, you are completely wrong. i have actually talked to Apple. the problem is corruption in the files. these files must be removed and replaced.
ive got an 20gig photo ipod, and every time the sync gets to around 5.8gb it crashes and comes up with error -69. ive tried removing the bad songs and restoring the ipod. i even formatted my library and re imported the songs. however i also found that the songs which have apparently caused the error are now syncing. so im very confused, i dont want to have to take it to apple, as they’ll make me pay through the nose for a repair. any ideas?
thanks