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Experience:  Apple Certified Desktop & Portables Technician, A+, Cross-Platform (Mac/PC) Tech - for over 14 Years
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An old Nano 8gig wont automatically sync when I plug it into

Resolved Question:

An old Nano 8gig won't automatically sync when I plug it into my Mac. I'm a new mac user and still learning the computer. I don't even have a printer connected yet. Anyway I can get this i-pod to sync?
Submitted: 5 years ago.
Category: Mac
Expert:  MacTechTrainer replied 5 years ago.
Hello and thank you for asking your question, with
I am Sr. Mac Tech Support Specialist, Terry, glad to assist you.

**Please note: An "Answer" by me, or an"Accept" from you, does not mean the session has ended. So please remain patient with me and I will work
diligently, to resolve your technical question to your satisfaction.-Thanks!*
Here are some steps you can try to resolve the issue:
• First, if you have not already done so, download and install iTunes 9.2.1 if the current version of 10.2.1 is too new for you to install on your Mac
Download and Install iTunes 9.2.1 for Mac

This version will hopefully do the job for you and your older iPod Nano.

• Once you have this version of iTunes installed, then I would recommend you attempt to sync your iPod once again.

This is my first answer, but certainly not my last, as long as this issue remains unresolved.

I will be watching for your reply.

If you have any more questions, regarding your technical issue, please feel free to reply to this post as I am always ready to assist. Thank you!


Customer: replied 5 years ago.
Hi Terry:
Hoe do I get back to you after downloading 9.2?
Expert:  MacTechTrainer replied 5 years ago.
Not to worry!

Just bookmark this page in your web browser, and then when you are ready, just reply back to me.. I will be alerted when you are back. :)

MacTechTrainer and other Mac Specialists are ready to help you
Customer: replied 5 years ago.
The computer says I have 10.2.1 loaded
Expert:  MacTechTrainer replied 5 years ago.
So considering you have iTunes 10.2.1 installed already, what exactly happens when you connect your iPod Nano?

• Are there any error messages you see, that pop up when you do connect your iPod Nano?

Customer: replied 5 years ago.
The computer says 10,2,1 is loaded. Nothing has changed,
No error messages, the "sync ipod " buttons is grayed out.The only thing that happens is the I-pod will charge.
Expert:  MacTechTrainer replied 5 years ago.
This is just a courtesy update to let you know I am still here.

Please be patient with me if you would, I am determining an answer for you. I have an idea what the issue could be, but just checking a bit further before I pass this next procedure on to you.

I will be with you shortly.

Thank you,


Expert:  MacTechTrainer replied 5 years ago.
Here are some steps you can try to resolve the issue:

First, disconnect your iPod from your Mac.

• From your desktop, click anywhere on a blank space on your desktop. Now you should see Finder listed near the Apple menu icon.

• From the Finder menu, click on Go, then Home from the drop-down menu. This will take you to your Home folder.

• Locate and open the Library folder

• Within Library folder look for the Preferences folder and open it.

• Locate and remove to the Trash, these files:

Once you have removed these files, then click the back button on your open Finder window. This will return you to the Library view.

• Locate and Trash the folder entitled Caches

Once you have done that, close all windows, click on the Apple menu icon located in the upper left corner of your screen and select Logout <username>, so you can log out of your user account.

*Once you are logged out, simply log back in. This action will restore all the files and folders you just trashed, with new copies of each.

Before attempting to reconnect your iPod to your Mac and running iTunes again,


Go to Finder Menu bar
• Click Go > Utilities > Disk Utility and open up Disk Utility app.
• Click on Macintosh HD volume (or on the name you have changed
this volume to.)
• Select "Repair Disk Permissions"

*Let Disk Utility run this repair permissions until completion

Once Disk Utility is complete and there are no errors in red in the completion summary (if there are errors listed in red, re-run DU to see if those error will clear- if they don't reply back to this post right away and let me know what the exact error message is), quit Disk Utility.

• Now attempt to reconnect your iPod and relaunch iTunes

Let me know how this works. Thanks for your patience!


Customer: replied 5 years ago.
I followed your instructions completely. No errors showed up in DU. Plugged in Ipod. Launched Itunes.
However, when I launched I-tunes, the sync ipod button was still grayed out.
Nothing on the Ipod visual menu except Ipod charged (no message saying do not disconnect ipod syncing)
Expert:  MacTechTrainer replied 5 years ago.
Thanks for the update.

I believe I have an article for you from's forum which has a few steps you
can follow to help get your iPod Nano working on your computer with iTunes. This is especially applicable, if your iPod Nano has been synced to a previous computer.

Link: Sync iPod is grayed out

Try the few procedures suggested in this article, update me when you can.

Thanks for your patience thus far for this session!


Customer: replied 5 years ago.
Aw, doggone it, I must be among the dumbest people in the world. I just finished reading and documenting your latest message - about RESTORE. I cannot find a restore or summary button anywhere. Not in file,edit,view, store,etc. I would gladly try to RESTORE if I could find it. However, a few months ago when I bought this Macbook, I think it auto synced stuff until this latest problem. Anyway, Where is the RESTORE?
Sorry, Terry, you've evidently got a dummy here on this one.
Expert:  MacTechTrainer replied 5 years ago.
Thanks for your update, and no you are just fine. I have provided for you below, a screen shot image of what you should see, if your iPod is connected properly to your computer in iTunes.

The main tab that appears for the iPod when connected to your computer and showing up in iTunes, is the Summary tab.

If you view this screen shot, you will also see under the Summary tab, the Restore button.

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Let me know if this example screen shot helps you to see how to locate the Restore button with your iPod connected to your computer.


Customer: replied 5 years ago.
I can not get to the page you sent me. My I-tunes page does not show any devices connected. I got to a page somewhere else, found a DEVICE tab, clicked on it and the window was blank.
I haven't seen the page you sent me in a long time.
Expert:  MacTechTrainer replied 5 years ago.
Thanks for your reply Dave.

One question I did not ask you earlier, may help me to better assist you--
• What version of Mac OS X are you using on your Mac?
(i.e. "Mac OS X 10.6.6 or Mac OS X 10.5.8, etc" -)
( If not sure how to check version of Mac OSX system- Click on Apple icon (Apple Menu) on upper left corner of screen- from the menu select "About this Mac" - you will see your version in the popup window)

Also if you would, so I can get an exact bearing on what model of iPod Nano 8G model that you do have, click the link below and under the section for iPod Nanos on the Apple Support page, please identify for me, which model you have:

Apple iPod Support Main Page

By you providing me these few details, I can move much closer to honing in on the issue you are having with your iPod not being seen by your computer and your iTunes application.

Thanks Dave, I will watch for your update.


Customer: replied 5 years ago.

Yo Terry:

The Mac is - Mac OS X 10.6.7

The Nano is (I think) 2nd generation. It is - model# A 1199

Serial Number (if that helps) is- ym7277g6vqt


thanks for your patience.


Customer: replied 5 years ago.
It has been a while, I have not heard from you. I can not get to the page you sent me, i have not seen this for some
time on this computer.
Customer: replied 5 years ago.
Are you out there? It's 4/25/11. Have not heard back from you since 4/11. The page you want me to see IS NOT ON MY COMPUTER.
Expert:  MacTechTrainer replied 5 years ago.
Hi Dave,

I was looking for your post! I am so sorry we missed each other. It appears our session had timed out, which is why I did not see your question listed, in the active questions pending section of my worklist.

If you would, please allow me a bit to revisit our previous correspondence and I will reply back with updated steps and or adjustments to my past recommendations, in order to assist you. This is a priority session now so I will be with you today, until resolution. I will also make sure this session does not time out again, until I have fully resolved your issue.

Thank you.


Expert:  MacTechTrainer replied 5 years ago.
Hi Dave.

I have been going over some possible scenarios as to why your iPod Nano is not working with iTunes and I have another process I would like you to try:

So here is what I would like you to try next:

I would like you to create a new user account so that we can test if the
issue you are having, is specific to a single User Admin Account
or System-wide, affecting all users on your Mac when it comes to the iPod Nano working with your iPod Nano. The outcome of this procedure will allow me to determine the next course of action I can advise you to take.

-CREATING A NEW ADMIN USER- (for troubleshooting purposes)

• Click on the Apple menu icon in upper left corner of your screen. Now select System Preferences from the drop down menu.

• From within System Preferences, select Accounts
• When the Accounts window opens, click on the padlock icon
at the bottom left corner and enter your Admin User
password for your Mac, when the dialog box pops up.

• Once you have full access to the Accounts window, click the "+" button, which is located just above the padlock you just clicked.

• Create an new user with the User name "test" and use a password like "test or "password" as a generic password.

• Make sure to click the check box for " Allow user to administer this computer", to make sure that the test user has full Administrator rights.

• Once you have committed this new user, quit System Preferences and close all windows and applications.

• Now once again, click on the Apple menu icon and select
Logout <your username>, located at bottom of the menu, and you will be logged out.

•From the login window that you are at now, select the New User account you just made and with your generic password, log in to that account.

• When in that new User Account proceed to launch iTunes from the Applications folder.

• Now attempt to connect your iPod Nano, in this new user account.

Let me know if there is any change in how the iPod Nano works or not.

I will be watching for an update, so let me know as soon as you have time to do so.


Customer: replied 5 years ago.

Ok: I went through the steps you required. The "test" loaded I-tunes with nothing, I mean none of my music, just generic music categories I suspect are found on brand new accounts. I went back to my original account and at least my music loaded.

Doesn't look like this is a fix.


Customer: replied 5 years ago.

Hi Terry:

It's been a week since i tried your last "fix"

Are you giving up on me and my problem?


Expert:  MacTechTrainer replied 5 years ago.
Hi Dave, no, not at all. I will be active on this question until we can go any further, so that is a big no, because I don't give up

I believe your question has kept timing out, so I did not see it in my active Awaiting Expert queue, not until it was re-listed again today. Sorry about that technical issue in our system.

Ok, now since you have tried wit the new user to sync your iPod and it still would not
sync your music, I would like to draw your attention back to your original user account, where you noted your music loaded.

Are you at this point trying to sync music from your iPod Nano into the iTunes library or sync music from your iTunes library into your iPod Nano?

Let me know this, and I will start trying to isolate the issue from there.

Thanks Dave,


Customer: replied 5 years ago.
Not entirely sure I know what you mean. I have never tried to move anything from the I-POD to I-Tunes. All I have ever done is plug the I-POD in for charging and the computer took over. I use to see a little message saying "do not unplug I-POD is syncing" or something like that. When I stopped seeing this message is when I contacted you folks.
Expert:  MacTechTrainer replied 5 years ago.
Thanks for the update Dave. Let's try another route here:

Try resetting your iPod:
• Press and hold the Menu and Center click button.
• Keep the buttons pressed until the Apple logo appears.
• When the Apple logo does appear, release the button and let the iPod Nano start.
• Connect the iPod to your PC and see if it is detected.

When you connect the iPod to your PC and it still yields that same error message, then you may need to try a different USB sync cable, as sometimes, with as much troubleshooting as is done, the issue can actually be with the USB sync cable.

If this does not work Dave, I would have no choice but to recommend you take your iPod in to your local Apple Retail Store or Apple Authorized service center, to at least have a Mac tech perform a hands-on diagnostics of the device to determine why it is not syncing.

These are simple devices that do not have a wide range of troubleshooting issues. If this turns out to be a hardware related problem with the syncing of your iPod to your PC, then that is where hardware service may be required.

Update me and let me know if the hands on reset works for this syncing issue with your iPod Nano.

Thanks again for the update and please post me when you can.


Customer: replied 5 years ago.
You ain't gonna believe this. THAT DID THE TRICK. MY SYSTEM WORKS AGAIN.
Yippie. Thanks for sticking with me. Now I can make a new list of songs to go with my Nordic Track.
That's what i was trying to do weeks ago when this all started.