Music purchased on an old computer will not sync

Hello country2012,

I would suggest recreating your iTunes library if not everything is showing in the sync window.

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

http://support.apple.com/kb/HT1451

Re-creating the iTunes Library file

Note: After re-creating your library, any devices that you sync with iTunes (Apple TV, iPod, iPhone, iPad) will see your iTunes library as a new library and will completely resync. The next sync with such a device will take longer and may reset some options since your rebuilt library isn't familiar to the device.

1. Quit iTunes.

2. Locate your iTunes folder (this is the folder that contains the iTunes Library and iTunes Library.xml files).

Operating System	Default location of iTunes Folder
Mac OS X	/Users/[your username]/Music
Microsoft Windows XP	\Documents and Settings\[your username]\My Documents\My Music\
Microsoft Windows Vista	\Users\[your username]\Music\
Microsoft Windows 7	\Users\[your username]\My Music\

3. Open your iTunes folder.

4. Drag the "iTunes Library.xml" or "iTunes Music Library.xml" file to the Desktop. If neither is available, learn how to add files back to the Library (because the XML file is not available, playlists and other information will not be available).

5. Drag the following file from your iTunes folder to the Trash:

Mac OS X	"iTunes Library" or "iTunes Library.itl"
Microsoft Windows	"iTunes Library.itl"

6. Open iTunes.

Important: Do not add any content into iTunes at this point (such as by purchasing something from the iTunes Store).

7. Choose File > Library > Import Playlist.

8. Navigate to the "iTunes Library.xml" file on the Desktop.

• Mac users: Click Choose.
• Windows users: Click Open.

If your Podcasts list in iTunes is empty after following these steps, learn how to add them back into iTunes.

Cheers,

Sterling

country2012 wrote:

Anyway...all of my songs from the library on my laptop successfully transferred over to the desktop and show up in the iTunes library. I Authorized the desktop computer and activated home sharing for both computers. I downloaded several songs on the desktop computer and plugged in my husbands iPod. to my surprise...when I went to sync the new songs on the iPod...a message said it would have to clear all of the old songs from the device, and the old songs that were listed in my library are not listed on the sync menu library....

You are syncing to a new library on the new computer. Simply having the same songs on both computers does not make it the same library.

Rebuilding the library as suggested by sterling r will not fix the issue.

You need to copy the entire /music/iTunes/ folder from old computer to /Music/ on new computer.

See this -> http://support.apple.com/kb/ht4527