Music Won't Sync/Files Start Disappearing

I have an iPhone 3G 16GB with 3.0 and a new iMac with Leopard 10.5.7. Lately I have been having issues, when I sync my iPhone with iTunes it gives me an error saying iPhone not authorized. Then when I go to play a song in iTunes, they all say Locate. When I go to my External Hard Drive where they are stored, the files are all missing. My hard drive still shows the same amount of space free but the files/folders are missing. If I unplug my iPhone and restart my iMac the files are there again and I can play my iTunes music but if I plug the iPhone back in, the issues presents itself again....
How can I fix this? I restored my iPhone but it still does it.

I've tried that. I've changed the settings under Summary with no success and also made sure the Sync Music box is checked. When I check the Sync Music button the Capacity at the bottom of the screen recognizes the music and the capacity jumps from 0.18 GB to 4 GB, but when I hit apply and iTunes syncs the music doesn't transfer to the phone.

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Apps won't work and music won't sync after IO5

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I had the same issue....you will need to call Apple support for assistance...when you do, be SURE to get someone who is competant!!!! I got a dumb a** and they did not instruct me properly and I lost EVERYTHING on my phone!!!! What started out as a simple fix/problem has turned into a catastrophe! Good luck to you

Music won't sync in ios 8.1

iTunes impossible to sync - My itunes music won't sync. I have tried it all, resetting, deleting the library and reloading, turning on and off all the possible related buttons on iphone and itunes and still mosto of the music is still with a doted circle on the left that keeps the song grayed and although I hit SYNC nothing happens. Then, there are songs on the iPhone 6 that are not on the iTunes library. How can that be possible?

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HT1351 some of my newly purchased music won't sync

Some of my newly purchased music won't sync, even though I converted it to the proper format.

Music purchased from the iTunes Store does not need to be converted before being used on iPods. Music from most other sources, such as Amazon, is in MP3 format and does not need to be converted. So, can you explain "even though I converted it to the proper format"?

IPhone music won't sync with new iMac computer

I've been using a PC with my iPhone. now I use an iMac and transferred my entire iTunes library from the PC to the Mac, but the music won't sync to the iPhone. I've tried restoring the phone and everything but nothing seems to be working. help?!

What are your selections under the Music tab for your iPhone sync preferences with iTunes?
Are you syncing contacts with the Address Book and calendar events with iCal on your Mac and if so, are your contacts and calendar events synced?
Have you selected any photos on your Mac to be transferred to your iPhone and if so, are the photos being transferred to your iPhone when syncing?
Long story short, do all other selections under the various tabs for your iPhone sync preferences work except for music?

IPod found by iTunes but music won't sync???

iTunes recognized my iPod device but the sync test says no iPod found and music won't sync...any suggestions???

Remove and reinstall iTunes by:
Removing and reinstalling iTunes and other software components for Windows Vista, Windows 7, or Windows 8
Next, try
Try DFU mode and then restore to factory settings/new iPod via iTunes
How to put iPod touch / iPhone into DFU mode « Karthik's scribblings
Try on another computer as a test to help determine if you have an iPod or computer problem. You will have to restore the iPod on this computer.
- Last, make an appointment at the Genius Bar of an Apple store.
Apple Retail Store - Genius Bar

Everything is going nuts. and now it won't play music, won't sync. help!

I really need your help. You see I own an 80gb ipod classic. And I bought a bunch of new songs on iTunes yesterday so I want to add them. I tried syncing it but it won't add the songs, instead it messed them all up. The songs that were already added either have a messed up art work, don't play, freeze my ipod or only play halfway. I have bought at least 90% of my music from iTunes so the files aren't damaged.
I really need to fix this, because now not even the hard disk will work and I have over 15gb of valuable content in there. So I need all the help i can get to solve this problem. Help me please!

so I restored it, it took a lot since I had so many files to save.
and even if i restored it nothing works.
now it won't sync ANYTHING. from videos, to photos and songs.
i mean, nothing.
what is wrong? i'm seriously thinking or returning this ipod. it's crap.

Most of My Music Won't Sync

I'm having an issues with Itunes and all of my devices. I have over 12,000 songs in my itunes library. All of these songs will currently play fine in itunes and I can listen to them on my computer - no issues. I used to be able to take any of these songs and sync to any of my apple devices. I can't anymore.
When I click "entire music library" to sync to device, and it doesn't matter which device, it shows about 3GB of data along the bar at the bottom of the screen. It shows 12,000 songs selected, but the data shows as 3 GB, I know that the size of those files is actually about 92 GB, but itunes only seems to recognize about 3 GB.
So long story short, there are some songs that I can sync to a device at the moment, but most songs will not sync and I don't know why? They are all the same types of files, when I go into the properties and examine all of the settings, I cannot see any difference between the files that itunes will "recognize" versus the files that it will not recognize - what's happening?
Please help!

More than likely, it's not all there. Either the files have been moved/non locatable, or they're not all downloaded. Check HT2519 to make sure all purchases are downloaded, and go through any music brought in from CDs or downloads by going Start Button - Music - iTunes and check those folders to make sure all your songs are there.

Selected music won't sync.

I thought I had this cracked but ....
I've checked the box next to 'Sync only ticked songs & videos' on the iphone summary screen.
I've checked all the boxes of the music I want on my iphone...
Go back to the iphone summary screen & on the music app Entire Music Library is checked & click sync.
but only a few songs appear
if I choose selected playlists, artists, albums & genres (but not tick any of the checkboxes below it... some songs disappear...
not sure whether this is relevant, i'm sure it is... but not sure what i can do about...
if i tick boxes in the itunes library or untick for that matter... when i then go to my device music folder(bottom left) they don't seem to correspond (the ticks)& the music that seems to be appearing / disappearing as mentioned above are some of the ones that won't budge or disappear.
If this is confusing ... I apologise... but it's confuding for me sat here trying to work out what i'm doing wrong & trying to translate it the best i can.
Apologies again... Looking forward to an uncomplicated answer ;-))

Allan Sampson wrote:
I suggest creating your own iTunes Playlist or multiple Playlists to be transferred to your iPhone.
Place the music you want available on your iPhone in the created Playlist or Playlists, select Selected Playlists under the Music tab for your iPhone sync preferences and then select the Playlist or Playlists that you want transferred to your iPhone.
When placing music in a Playlist, you can view how many songs are available in the Playlist, and the size of the music in the Playlist at the bottom of the iTunes window when the Playlist is selected in the iTunes source list before syncing the Playlist.
Obviously I can do that. I want to know how to get iTunes to work as it is supposed to.
Is there a quick way to generate a playlist that is a certain size, say 10GB?
Thanks

Music won't sync to iPhone

Informations:
-iPhone 5 (running iOS 7)
-iTunes 11.1
-windows 7
Issue:
Exactly how it sounds, the iPhone just won't sync music anymore. I have enough space for it. I made sure the option for music is checked.
Everything else will sync to my phone just fine. My iPad also successfully syncs the music (so that weeds out the possibility of a corrupted file)
Half the time the iTunes sync won't even complete, it will either stay stuck on the last step, or automatically cancel
I am not sure what to do, the advisors chat page says there is no solution available in my area, and the tech support over the phone keep hanging up :(

Found out one of the songs had an emoticon/symbol in it, which was causing the new itunes to prevent all the songs from syncing... thanks for not responding to me

My music won't sync

I imported an album awhile ago & ever since then half of the songs on my ipod touch were deleted & won't go back on. I've tried checking the boxes of the songs I want synced & restored it twice but nothing worked. The summary in my ipod tab says I have 711 songs but the music tab says I only have 609. What can I do to fix this?

This is correct.
The music sync is one way - computer to ipod.
It has always been very basic to always maintain a backup copy of your computers files/docs/pics/music/etc.
Use this to put everything on the new computer.
If for some reason you have failed to backup ( not good), then you can transfer itunes purchases from the ipod:
Without syncing - File>Transfer Purchases

Ever since the new update, my Ipod won't sync. Starts to sync but then goes back to connected eject before disconnecting. Still won't transfer songs even after being restored. Restored fine. But now I've got nothing on it. Please god help!

For awhile, since the newest update, I'd noticed when charging the ipod (classic) that it stopped going to the charging screen and would stay on the Connected: Eject before disconnecting' screen. But, y'know, didn't matter to me, it still charged... until today when I tried to add music. Tried it many times, reset it... STILL wouldn't transfer songs... It would 'say' it was syncing, but then suddenly stop and stay on the same Connect: please eject before disconnecting' page. I did a couple of times get a message about scanning it but, after restoring that never popped up again...
So, I do a system restore on it and ofcourse THAT works, but it STILL won't sync! So, now I've got an ipod with no music that won't sync and because it's all gone on there, I'm not sure how to back up my stuff (should I need to re-install iTunes... Though I doubt it'd work...)... So, yeah, I tried a different cable too, still no luck...
There has GOT to be some way to fix this!
Please somebody help me out! I so freaking appreciate it you have NO idea!

I think the problem is that the iPod got set to Manually manage music and videos. It needs to be set up for automatic syncing again. Just unchecking that Manually manage music and videos setting does not do it.
In iTunes 12, select the iPod in iTunes (using the device button), so that you see the iPod's "management" screen. In the sidebar (along left side of screen), there are two headings (Settings and On My Device). Under Settings, click on Music. To the right, you see the iPod's Music screen, where you tell iTunes how to sync songs to the iPod.
Check the box at the top for Sync Music. That turns ON automatic syncing for music. Below that, choose the option to sync Entire music library (assuming your music library fits completely on your iPod). Otherwise, you can choose the option to sync Selected playlists, artists, albums, and genres and make your selections below. Then click Apply.

My music won't sync from computer to ipod

My music( 234 songs, no videos or movies) won't sync from my computer to my ipod. This is really annoying and I had 42 songs on my ipod, knew I was missong 90 or so songs, synved it and checked my ipod...19 songs. I was so annoyed. It is not about space because the songs take up 1.18 gb and I have 1.71 gb left. Please help because I am getting to that stage where it is not about games but songs.!

Do you have any Restrictions set that would prevent sysncing those songs? Settings>General>Restrictions
Try:
- Reset the iOS device. Nothing will be lost
Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Unsync all music and resync
- Reset all settings
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:
iOS: How to back up
- Restore to factory settings/new iOS device.

IOS 7, some music won't sync

I just updated to IOS 7 and I downloaded new music ( i updated itunes already) and when I synced it, its fine but some of the music won't play it is greyed out with a red circle. PLEASE HELP

Does the non-syncing music play in iTunes on the computer?
If so then
Try:
- Reset the iOS device. Nothing will be lost
Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Unsync/delete all music and resync
To delete all music go to Settings>General>Usage>Storage>Music>Tap edit in upper right and then tap the minus sign by All Music
- Reset all settings
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:
iOS: Back up and restore your iOS device with iCloud or iTunes
- Restore to factory settings/new iOS device.

HT2527 Music won't sync to ipod

I have purchased some new music on itunes on my computer with windows 8. Wehn I try to sync my ipod the music won't transfer to the ipod. Any thoughts?

You can only automatically sync all media to one computer/iTunes library. You can sync music and videos from any iTunes library/computer if you use the manual method included here:
iTunes: Syncing media content to iOS devices and iPod
If you wan to make this your one syncing computer/iTunes library:
Syncing to a "New" Computer or replacing a "crashed" Hard Drive: Apple Support Communities

Music Won't Sync/Files Start Disappearing

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