Itunes could not copy (name of song) To the ipod (name of ipod) Because an unknown error occurred (-50)

and attempted to drag them directly to the ipod when it is connected to the computer.

That wouldn't work as songs need to be stored in your iTunes library first before they can be synced or manually added to the iPod.

Speaking of which, do you normally manually manage your iPod contents by dragging content over to it from under the Devices section in the left hand pane of iTunes, or do you let it sync automatically with iTunes?

I just got my first smart phone (again $$$), and I'm told I can get music for free from Pandora, but I have no idea how to do that....maybe it will solve my problem.

That isn't true. You can receive free Internet based radio from them, but that's it.

I don't have any other relevant suggestions for you this point other than to perhaps wait a bit (maybe once the next release of iTunes is out) to try and sync these purchases to your iPod.

B-rock

Hi and thanks again,

First: When I mentioned that I attempt to drag the songs into the ipod as a device when attached to computer and Itunes is open, the source I am using for the music is 1) A USB device or 2) The Music file in My Documents.

All of the songs are in fact IN the main library, but will not sync to the ipod after numerous, time-wasting attempts.

It is my understanding that to, say, create or add to a playlist, one should be able to simply drag the songs from the library into the respective playlist. When I attempt to drag songs, either to a playlist or the device, it fails to transfer.

I have synched both manually, and automatically several times.

The most troubling thing is the lack of support from Apple and Amazon....we're just hung out to dry.

Well with the exception of your gracious help. Many thanks

And it fails due to the error message that you supplied earlier correct (error -50)?

B-rock

I am having a similar issue except it is happening with all of my music collection, I don't have any downloaded from Amazon. The songs have been synced to this ipod before and are located in my itunes library, nowhere else. I have been having numerous issues with things like this all of a sudden and have had to reset my ipod several times now. Currently, I ran a reset, managed to sync about 10.6 GB of music manually, and then hit the current roadblock.

Maybe tried rebuilding your iTunes library using this support article.

iTunes: How to re-create your iTunes library and playlists

B-rock

Hello All,

Yes, in answer to earlier Q: The error message I receive(d) is -50.

The situation now seems to be even more odd....

1) Some songs are showing up in the recently added Playlist, but NOT in the music library (no error message at any point)

2) Some songs DO show up in the music libray, but cannot...cannot be dragged, or added, or sync-ed to the ipod. (no error message at any point)

3) Some songs (from a complete album) HAVE been sync-ed to the ipod, but not the full album, and none of the remaining music will sync or drag.....(no error message at any point)

This has now gotten absurd....and who ya gonna call????? I was brutal in the follow-up email/evaluation that Apple sent me as a follow up to a help-line phone call I had last week that was largely useless.....The error messages don't even appear any longer...it's as though itunes has decided to simply ignore me, and my music. Ouch.

I tried the rebuilding of the library too a moment ago...with no improvement....

As a reminder: I am on Windows XP Media Center....though that has always been my OS...long before this began.

It can't be this hard can it?

Help (again)?

Thanks All

Have you tried completely removing and re-installing iTunes and all Apple related software and components.

Removing and Reinstalling iTunes, QuickTime, and other software components for Windows XP

B-rock

Saturday afternoon, and this is the first chance I've had to once again try and fix this issue.

So I did as you suggested and removed all Apple programs/files etc from my computer and reinstalled the current version of itunes...

Sadly, the issue remains unresolved. I no longer get erroro message -50, but the songs I am trying to add to my ipod simply don't show up after a synch. They are all in the main music library, but simply don't show up when I synch----either manually or automatically...it's as though they do not exist.

So my (recent) MP3 purchases from Amazon can be played while sitting at my comptuer, but not on/from my ipod...great... I work on my feet for 10 hours a day at a Ford assembly line, and without my ipod, I would go insane...this issue, I regret, is also driving me insane...I have better things to do with my precious day off.

Again any help/tips are welcome...hard to believe no one from Apple reads these posts or gives a **** about our problems...

Onward and upward

If you haven't tried this already, give it a shot:

Make a playlist with the songs in iTunes.

Highlight all of the tracks (CONTROL+A), right click, COPY.

Go to your "My Music" or "Music" Folder, create a subfolder, and paste these tracks into this new subfolder.

Return to iTunes, FILE --> Add folder to Library --> and add this newly created subfolder.

Attempt to resync once more.

Good luck. I understand the frustration, I would die without my Amazon purchases on my Apple devices.

If you right-click on one of your non-syncing tracks in your iTunes library and select Get Info, does the path ("where:") at the bottom look legitimate? My issue was iTunes couldn't actually locate the file since Amazon tried to automatically import it for me upon download (it showed up with \\?\ at the beginning). You can right click on the path and Show in Windows Explorer to make sure it exists and can be hit by iTunes.

If it's not a mapping issue, I would think it would have something to do with your sync settings. For example, when you plug in your iPod and it begins checking for files to sync, you can click on the device and choose "Sync only checked songs and videos." If that option is turned on, I would make sure the songs you're trying to sync are checked or otherwise, uncheck this option.

You could also try to make sure the files are somewhere in your iTunes Media Folder Location (Edit > Preferences > Advanced) and not somewhere else on your machine. I don't know how much of a difference that would make, but might be worth a shot at this point.

What a way to spend my Saturdays...did this same crap last week and the week before.

I spend an hour on the phone with Alex a senior tech from Apple today. He tried his best to provide answers, but the thing is, everything he suggested has been done...done more than once. Restore & resynch (3 times), Uninstall and reinstall all Apple programs (twice). Create .bat file and do that procedure (3 times)...

And his last suggestion, which took another 3 hours to complete, was to clear out all the songs on the ipod by unchecking the synch box on the music tab associated with the device, restart, and resynch...which just now completed with no success.

I tried siddenke's solution above, and while I was able to get the songs into my libary, the still will not synch.

I also looked at the location of the songs as suggested by artfuldodgr42, and the location looks legit: C:\Documents and Setings\Owner\My Documents\My Music\Amazon MP3\TheWho\Greatest Hits\17-Eminence Front.mp3

Alex from Apple who is totally cool suggested this may be a result of Amazon's changing for a format for their mp3's or something like that...but here's the thing:THE SONGS ARE IN THE MAIN LIBRARY OF MY ITUNES BUT WONT SYNCH TO MY IPOD.

There is no error message that accompanies this process...I synch, and when it is complete, the songs simply are not in the ipod...maybe the ipod is just dead...it's an old 120G Classic which the kids call an antique...but I like the capacity, just tired of the dial...and really really tired of spending soo much time on this.

I'm not giving up yet. Thanks all

Onward and upward

You could try using another application to sync your music. There are some suggestions here: http://www.makeuseof.com/tag/6-ways-to-sync-music-to-your-iphone-without-itunes/

I haven't used any of these applications, but I would imagine if it's an issue with iTunes handling the file mapping during the sync process, another application might not have the same issue.

If it's an issue with Amazon's file format, you could try using iTunes to create an MP3 version of the file. I believe Amazon music is an MP3 format, but iTunes uses a different encoder.

To do this, highlight the tracks you're trying to convert, right-click one of them and select "Create MP3 Version." It just takes a few seconds per song. You'll have duplicates of each file in your library, but I would leave the originals and the copies in there until you determine if it's going to sync the files.

I feel your pain. I spent hours trying some of Apple's suggestions before I figured out the issue on my own. Hopefully there's something that will work, short of replacing your device.

Good luck!

As I look at the file format for a song that won't synch, it says: MPEG, it further says MPEG-1, layer 3.

But the thing is, songs that DO synch have the same format...

I'll check out the alternaitve synch programs. thanks

Maybe run these MP3s through the MP3 validator software to make sure they aren't corrupted.

http://www.gromkov.com/faq/repair/mp3_validator.html

B-rock

The latest amazon downloader OR the latest iTunes get a defective path for amazon downloads. Delete the amazon added files from the iTunes library and use 'Add Folder' to readd them from your Amazon MP3 directory