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iTunes & iPod problem! Pulling hair out!

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Problem 1. I imported a CD to iTunes. When I dock the iPod, it does not copy the new play list onto the iPod. The preferences are set to auto update the iPod. The Contacts and Calendar updates fine, but not the play lists!


Problem 2. When I exit iTunes, I cannot eject the iPod. It always says it is being used by an application and won't unmount it, even though there are NO applications running!


I tried trashing two of the iTunes plist files with no change.


I am running Tiger with latest updates.


I have a 40 Gb iPod Photo. All was working fine until I imported that CD! I even trashed the imported files, and tried again with no changes!


ANY help would be GREATLY appreciated!

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I would try reformatting the iPod. Recently, my iPod was being screwy in that the album art was the same for every single song, and a lot of songs wouldn't play, even though they did before. I just reformatted, and everything is fine now. This might help the problem of it transfering playlists correctly.


Sometimes weird applications are using the iPod when it is plugged in. My antivirus software always scans new drives, but there isn't any window that displays this, it's running in the background. If it's still scanning the iPod drive when I try to eject it, it will give the same message saying it's in use. Try turning off iPod Disk Mode in the iTunes preferences, and when you quit iTunes, it might eject it.


Just some thoughts...

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Here is more info that may help.


The CD I tried to import was created by using CD Spin Doctor after recording a cassette tape. Then off to Toast to burn the CD.


Then I tried to import into iTunes (AAC). About 1/3 of the way thru the 4th song, iTunes was stuck. I enventually had to force iTunes to quit. I listened to the CD and sure enough, the song was corrupt. When playing the CD with iTunes, the song would stop right at the same point, and iTunes would stay stuck at that point.


So I skipped that song, and tried to continue importing the rest of the songs. The next song did the same thing. AARRGGHH! So I had to eventually force ITunes to quit, again.


I resorted to just importing the raw aiff files from CD Spin Doctor into iTunes which worked just fine.


But whenever I would try to update the iPod, iTunes would act act as if the new songs and playlist did not exist. They would not copy over to the iPod! Plus, the iPod will no longer unmount unless I shut down the Mac.


I tried changing the preferences to manually update the iPod, to not use disk mode, etc. But those preference changes do not 'stick.' Whenever I rerun iTunes, it always goes back to auto update and disk mode enabled.


My guess is the iTunes 'database' is corrupt because of having to force quit iTunes when it hung on the corrupt songs.


Is this a valid 'guess', and if so, can I get it fixed without having to manually reload all my music and playlists?


My current music still plays fine. My iPod still plays its existing music fine. However, I noticed one song had the wrong album art.



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I agree that a Reformat & Restore is probably in order for the iPod. If you haven't already, you may want to Repair Permissions on your Mac, too.

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