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Mac Tech
Mac Tech, Apple Specialist
Category: Mac
Satisfied Customers: 1597
Experience:  7 + Years Supporting Apple Products
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Hi. Have Mac 10.5.8, I pod Classic. No previous problems.

Customer Question

Hi. Have Mac 10.5.8, I pod Classic. No previous problems. Now getting Ipod cannot be synced. An unknown error occurred. (-39) Help, Please. Thanks. Rita
Submitted: 4 years ago.
Category: Mac
Expert:  Mac Tech replied 4 years ago.
Chat Conversation Started
Richard :

Hi Rita

Richard :

Which iPod do you have? You need to do a hard reset.

Richard :

1. Toggle the Hold switch on and off. (Slide it to Hold, then turn it off again.)


2. Press and hold the Menu and Center (Select) buttons simultaneously until the Apple logo appears, about 6 to 8 seconds. You may need to repeat this step.

Expert:  Mac Tech replied 4 years ago.
Chat Conversation Ended

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Expert:  Mac Tech replied 4 years ago.
Also, make sure your iTunes software is up to date with the laster version.

This should take care of the problem. :)
Customer: replied 4 years ago.
Hi Richard. Tried it 3 times but still get the same message. Rita
Expert:  Mac Tech replied 4 years ago.
Hi Rita,

Here's a couple more things for you to do/try-

-Download and install the latest version of iTunes?
-Have you tried de-selecting the music sync, doing a sync, then re-selecting music and syncing again?
-Try connecting your iPod to an another USB slot with no other devices connected to your system

Let me know how this goes please!

Thank you!
Expert:  Mac Tech replied 4 years ago.
Also, that error is associated with Widows. Are you trying to connect your iPod to
a Windows machine?

And here's some software that may fix this for you.

http://www.ipoddatarecovery.net/iPod-and-iTunes-Error-messages-or-Alert-messages.php

Edited by Richard on 7/2/2010 at 9:15 PM EST
Mac Tech, Apple Specialist
Category: Mac
Satisfied Customers: 1597
Experience: 7 + Years Supporting Apple Products
Mac Tech and 5 other Mac Specialists are ready to help you
Customer: replied 4 years ago.
Thanks Richard. I think one of the last suggestions worked. Have a great 4th.
Expert:  Mac Tech replied 4 years ago.
Thank you!!!

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