Unknown Error -69 When Syncing Music or Video

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Level 1

8 points

Unknown Error -69 When Syncing Music or Video

I get the error: ITunes could not copy "Track Name" to the Ipod "Ipod Name" because an unknown error occurred (-69). I'm fairly sure I've also seen (-50) also, very frequently all of a sudden. My Ipod is several years old and still in great physical condition. The error always occurs when I'm trying to put a music track or video onto my Ipod. Sometimes they'll go through fine, others not. I get the error and then Itunes says "Trying to update Ipod" before it freezes. When I reset my ipod, windows pops up a window saying that the disc may have errors and I should scan in order to fix it. Scanning and repairing does nothing. After the error, the Ipod will still play what is on it, but I cannot add anything new or plug it in without similar issues. I only remember getting this issue when the new (6 months ago or so) Itunes came out. I've tried using old versions but the same error occurs.

I'm beyond frustrated. I've had to format my ipod and find all of my music over again at least 10 times now.

Other weird things I've noticed:

Sometimes when I plug in my ipod to the computer, my Ipod is still usable and the Itunes doesn't recognize it as plugged in.

Freezing when I plug in my Ipod, reseting the Ipod makes the -69/-50 error definite.

Any ideas? Google says that the problem is fairly common but I haven't stumbled upon a solution.

iPod classic, Windows 7

Posted on Mar 7, 2012 12:29 AM

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Answer 1

Mar 7, 2012 5:49 AM in response to wtw4

To be of any assistance,

Which version of iTunes are you using?
What is your iPod firmware/software version as shown in the iTunes summary page?

Error -69 occurs when iTunes tries to send files to your iPod, but a file (or files) is unusable, if you have error 50 this time also then it is the iTunes needs to be re-install. And your iPod firmware need to be updated.

I can suggest you delete the file that is causing the problem, but most likely it is all the files, due to the iPod firmware or iTunes mobile device driver is somehow corrupted, due to a partially aborted installation, or Restore.

So try this.

Can you do a Hard Reset as below

After charging till full charge, at least 2 hours (preferably 4 hours)
Toggle the Hold switch, make sure you dont see the red mark when you do the next step
Reset the iPod -> Press Menu and Center button simultaneously for about 10 secs till the Apple Logo comes ON
Then release the buttons
Select your preferred language.

Here is the Apple support Article on the 5Rs

http://www.apple.com/support/ipod/five_rs/classic/

Then Re-install your iTunes

Put the iPod in Disk Mode

http://support.apple.com/kb/HT1363?viewlocale=en_US

Connect the iPod to a High Power USB 2.0 port at the back of your PC, and never use the USB Hub.

Disconnect all other USB devices, except the mouse and keyboard.

Select the iPod in the Device pane of iTunes, and click Check for Updates

If it says "Software is uptodate", Press Restore just the same, although this will erase your iPod.

Good Luck!

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Answer 2

wtw4 Author

Level 1

8 points

Mar 7, 2012 9:57 AM in response to wtw4

Thanks for the reply Bilbo_cheshire

1. I'm using 10.5.3

2. Firmware version is 1.1.2

I've done the hard reset often and it's always in disc mode.

I've had my ipod plugged into the front/top since I got my new computer, could this really be the issue? maybe the information transfer isn't constant and info is lossed when syncing?

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Answer 3

wtw4 Author

Level 1

8 points

Mar 7, 2012 2:53 PM in response to wtw4

Nevermind, formatted my Ipod, switched the cable to the back, put a lot of music on. Then, randomly when putting a video on, I got the -50 error again.

Insanely frustrating.

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Answer 4

Mar 7, 2012 4:26 PM in response to wtw4

So start using your PC USB 2.0 port at the back and never at the front.

When you got the video -50 error, were you using any other USB devices?

And unfortunately, your Windows machine has tons of security software running, checking and delaying the USB transfer process, which may cause the -50 error on the huge video files. Typically, music files are less than 10 Mbyte, but video files are at least 600 Mbytes.

So if I can suggest,

Disconnect the PC from the Internet, Stop all security software running, sync your videos.

iPod sync problem has more than 50 listed causes, so solving one, the others might just jump up on you in future, especially trying to interface iTunes with iPod Classic, with old firmware, slow USB port and slow hardisk.

Have a nice day!

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