How JustAnswer Works:
  • Ask an Expert
    Experts are full of valuable knowledge and are ready to help with any question. Credentials confirmed by a Fortune 500 verification firm.
  • Get a Professional Answer
    Via email, text message, or notification as you wait on our site. Ask follow up questions if you need to.
  • 100% Satisfaction Guarantee
    Rate the answer you receive.
Ask Vinod Menon Your Own Question
Vinod Menon
Vinod Menon, Support Specialist
Category: Mac
Satisfied Customers: 2872
Experience:  worked as a Tech support Associate for Apple products
Type Your Mac Question Here...
Vinod Menon is online now
A new question is answered every 9 seconds

Hi there, I cannot get my iPod Classic to Sync with my PC.

This answer was rated:

Hi there,
I cannot get my iPod Classic to Sync with my PC.
I have restored, restarted, rebooted, re... everything with the iPod
I have reinstalled iTunes, restarted my PC
I have tried to get advice from Apples' website, but the info doesn't match with what I'm seeing on my computer screen
There is no Sync button.
I have the latest version of iTunes and my iPod has been updated.
What is wrong with this bl**dy thing?!!

I am Vinod. I will try my best to help you resolve this issue.

Could you please tell me how did you restore the iPod?

Thank you
Customer: replied 4 years ago.

Hi Vinod.

first I reset it following Apple's instructions: press Menu & centre button together until apple logo appears. This caused it to 'unfreeze'.


I then pressed the iPod button on iTunes, which gave me the option to Restore. I followed the instructions. This wiped everything off the iPod and restored the factory settings.


I then plugged the iPod in again, and hoped it would sync. All my stuff is on the PC, but none of it has transferred to the iPod

Thank you, Andy.

When you connect the iPod to the computer, you can see your iPod name listed to the top right corner, correct?

Just click on the iPod name and now to the middle of the screen, you will find tabs such as summary, music, photos etc.

Click on the music tab, select either entire library or selected playlists after selecting "sync music" and now to the bottom of the screen, you will find the sync/apply button. Click on it and it should sync the songs.

Let me know if it does not.
Customer: replied 4 years ago.

Thank you for that advice. It has not solved the problem, but it is heading in the right direction. It appears now to have synchronised all my podcasts and 8 random songs. 4669 songs have not been synchronised. ??

So the podcasts have synced, not the songs, correct?
Customer: replied 4 years ago.

That's correct, no songs have synced apart from 8 songs.

I have ticked the "entire music library" button. Should I perhaps go for "selected playlists, artists..."?

Entire library select should sync everything.

Are you able to play the songs in iTunes. Just try playing 3-4 random songs (which did not sync to the iPod) and let me know
Customer: replied 4 years ago.

I've tried 4 songs. There seems to be a major problem as it says "The song... could not be found because the original file is could not be found. Would you like to locate it?"

That is the reason they are not syncing to the iPod. The songs in iTunes are just copies and the original file is somewhere in the computer. iTunes is not able to find the original file and hence that message.

What computer do you have? Windows xp/vista/7 or a Mac?
Customer: replied 4 years ago.

PC with Windows 7.


Vinod, I'm sorry but I have to out for about 3/4 hour. Can we please continue this a bit later? Sorry for messing you about

No worries...just reply to me once you are back.
Customer: replied 4 years ago.

Hi Vinod. Sorry about that.

That's ok. Let me know once you are ready
Customer: replied 4 years ago.



On your computer, lets go to start - music - iTunes - iTunes media

Are all your songs listed there?
Customer: replied 4 years ago.

Yes. Phew, that's a relief!


Lets open iTunes application.. Go to the songs section. Now drag the iTunes media folder into the iTunes application.

Let me know if it is adding the songs into iTunes.
Customer: replied 4 years ago.

Whereabouts exactly should I drag it to? It gives me a "no entry" icon above the songs, and nothing seems to be happening when I drag it into the songs area.

Sorry, I lost what I typed. Please give me 5-10 minutes to retype
Sorry about that. I am typing from my phone and twice I pressed the back button accidentally which removed everything.

Lets try it this way.

Open the iTunes application. Now you will find a small box to the top left corner followed by a downward pointing arrow. Click on that arrow and select "view menu bar". Now click on the "file" menu and select "add folder to library".

Let me know once you are there.
Customer: replied 4 years ago.

OK, I'm ready for the next bit. Thank you.

Select "add folder to library" and navigate to the iTunes media folder we detected in music\itunes and try o add that folder

Let me know whether it adds the songs into itunes
Customer: replied 4 years ago.

Clicking on iTunes media didn't do anything. There was another folder called Music, so I clicked on that. It has started "processing" songs in a pop-up box called Adding Files, so I guess it's adding the songs to iTunes.

Ok. It should be showing a progress bar at the top (it may show the number of songs getting added, is it?)
Customer: replied 4 years ago.

Well it's now showing "processing album artwork", so I suppose the songs have already finished adding.

There are duplicates and triplicates of many songs (presumably from different albums). Is there an easy way to remove dupes?

There is, but that is a bit of a task.

Let's first sync your ipod and check whether the songs get added to the ipod. If they do, we will go ahead with deleting the duplicates.
Customer: replied 4 years ago.

Sounds good to me. I've just tested half a dozen songs on iTunes. The first dupes don't work, but the second ones seem ok.

iTunes appeared to close by itself (?), so I reopened it and now it's syncing with the iPod


Let me know once the sync is complete.

Check whether the songs are copied into the ipod.
Customer: replied 4 years ago.

Hi Vinod

the sync is complete and the songs (+ all the dupes) have loaded onto the iPod.


If you could please help me to delete the dupes, it'll be a successful afternoon's work.

The best way to remove the duplicates will be to remove all the songs from the itunes and reload the songs again. There are other ways too, deleting one by one or arranging the songs by time and deleting the older ones, but with more than 4000 songs, that may not be feasible.

So I would prefer deleting all the songs and readding them. Here's the process.

First of all, make a backup of all your songs. You can copy the songs in the itunes folder within the music folder and save them somewhere in your desktop.

Disconnect the ipod. Now open the itunes application. Click on any one song and select "Ctrl+A". This will select all songs in the library. Now click on the "delete" button.

The first question it will ask you is "are you sure you want to delete the songs". Click on "delete songs".

It may come up with a different question "do you want to move the songs to the recycle bin or keep it in itunes media folder". Click on "Keep file".

This will delete all songs in the itunes library. Now as we did earlier, click on File menu > add folder to library and select the folder with the songs.

Once they are added into itunes, you can plug in your ipod and sync it.

Let me know if you find any difficulty.
Customer: replied 4 years ago.

That's great, thank you. Unfortunately my PC reckons backing up the songs to the desktop is going to take 2 hours & 5 minutes.

Once I re-sync my ipod, will the dupes on that automatically disappear?

yes, they will disappear when you resync the ipod.

Actually the backup is not needed. We are doing that just to make sure you don't lose your songs, even if something unexpected happens while deleting the songs in the library.
Customer: replied 4 years ago.

Hi Vinod,

the back up has completed. I've deleted the songs on iTunes and am now re-adding them from the iTunes media folder.


Even if it goes wrong now, I think I can rescue it, but I'd be very grateful if you could hang around a bit longer, just to make sure.

no problem, I am right here.
Customer: replied 4 years ago.

The songs have finished getting onto iTunes and the dupes are still there. To be honest, I don't care. I'm just happy to have my iPod working with both music and podcasts downloaded.


However, it would be nice to get rid of the dupes if I can. I'll just try various things, and if necessary I'll get rid of them one by one.


If some of the duplicates are grouped together, you can just select one, then hold down the shift key and select the last one in the group. They all will then be selected at once. Then you can delete that group.

If they are not grouped together, hold down the control key and select the songs you want to delete.

Hope that helps even though it takes time..
Vinod Menon and 2 other Mac Specialists are ready to help you
Customer: replied 4 years ago.

Thank you very much for all your help. As you promised I am 100% satisfied, and I've added this page to my Favourites. I'll Rate you Excellent, and recommend you and this service to my friends & colleagues. Thank you.

Thank you very much, Andy..:)

Hope you have a great day!!
Customer: replied 4 years ago.

Yes that would be the turn sig switch .The head lights where inop

Sorry Andy, I did not understand what you meant. Could you please explain?
Customer: replied 4 years ago.

That last message was not from me !!

I am sorry. I just wanted to confirm.