Question about Apple iPod classic MP3 Player

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Unknown error (-69)

I'm so frustrated with Apple now!!!!
I purchased my iPod in Dec 2006 and never had problems with iit till now. I have 3059 songs iin my library. A week ago I purchased a purchased a few CD's, and tried to copy them onto my library. Fine. Then synchronising with the iPod: it ran and fully synch'd 1382 songs, and gave me this error message:

"cannot synchroise with "LIVINGSTONE" (that's me) due to an unknow error (-69)."

I have done everything to get my music onto my iPod - rebooting my computer, installing the latest iTunes, re-formating my iPod, all to noo avail. I have wasted way too much time trying to get hold of Apple/iTunes support to get this solved over the phone. To no avail. I have wasted too much time on the web searchiing for solutions!!!!

I'm so pissed off right now. I need to know:

1. what's the solution please?
2. after i solve the problem, how can i move my services elsewhere: i think Apple has become such a monolithic creature that's way too hard to get hold of that I must move my patronage (and all my music) elsewhere.

my email address: livingstonemoyo@verizon.net

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  • Anonymous Aug 14, 2008

    i have the same problem. i recently installed a new ear phone jack/hold button and it seemed to be working fine for about 3 weeks then all of a sudden when i synced it up, it had to go through ALLLLL the files to sync, and then it froze with the dreaded error -69. I have gone through all the suggested steps listed on Itunes (apples) website to no avail. Their suggestion is that one or more of the files have become corrupted and therefore cannot be installed, and hangs. I don't buy it, because it was working fine for one minute and then all of a sudden more than half my files are corrupted? Plus I tried to sync it up with my work computer and had the same problems, so according to Apple, both my work computer and my home computer corrupted my itunes library at the same time. Hmmm do ya think?!?!

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Posted on Sep 22, 2008

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Posted on Jan 02, 2017

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I am trying trying to sync my ipod and i keep getting a -69 error


Thank you for contacting Fixya Support, I am glad to assist.

An -69 error with an iPod occurs when iTunes sends a file or few files to your iPod, which may be corrupted and therefore unusable.

In order to remedy this issue, it is advisable to run the latest iTunes update and per this link directly from Apple Support which address this issue, try the steps provided in this support link below:

iTunes -69 error when syncing with iPod

Follow the steps listed in this Apple article and you should be able to regain access to syncing your iPod in iTunes, whether on a Mac or PC, without further issue.

Let me know if this helps.

Regards,

-Mactechtrainer


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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 *** and make it line up with the process on your PC. You're all welcome in advance.

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To find out what file is bad and will not upload onto your iPod, this Support Page from Apple tells how you may find the corrupted file:

http://support.apple.com/kb/HT1210

To perform a reboot on the iPod instantly, hold down the Select and Menu buttons at the same time for about 10 seconds until the screen goes black and the Apple logo reappears while the iPod is re-booting.

http://support.apple.com/kb/HT1320

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Try the link below that applies to your computer OS:

http://support.apple.com/downloads/iPod_Reset_Utility_1_0_3_for_Mac
http://support.apple.com/downloads/iPod_Reset_Utility_1_0_4_for_Windows

Useful troubleshooting-video:
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When you try to sync files to any iPod in iTunes on a Mac or Windows computer, you might see the following -69 error message:
"Attempting to copy to the disk failed. An unknown error occurred (-69)"This error occurs when iTunes tries to send files to your iPod, but a file (or files) is unusable (something is wrong with it).


To figure out which file (or files) is causing the error, update to the latest version of iTunes and then do this:
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  2. Watch the display at the top of the iTunes window while your iPod is being updated. The name of the problematic file should appear in the display right before the error appears.Then remove the bad file from the list of songs to be synced to your iPod:
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  7. Deselect the checkbox next to the file name.
  8. Repeat steps 1 and 2 to update your iPod. If you have multiple problematic files in your iTunes library, you may need to repeat the other steps to remove them too.
To prevent future issues, you should delete the unusable files from your iTunes library, then restore them from a backup or reimport them from a CD.


If you're not able to isolate to any single file or if another iPod works with the same songs, then disconnect any other devices connected to USB or FireWire and try again. If the issue continues, then then try resetting your iPod. If the issue continues, then restore your iPod.

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