ITunes telling me to repeatedly authorize account to sync ipod

I moved my iTunes from my PC to my Mac, and everything works great, except when I tried to sync my iPod with my Mac; iTunes repeatedly tells me to authorize the account/device/whatever, and when I do, it confirms authorization...but when I try and sync it again, the same thing happens over and over and over. Anyone have a clue what to do? I"m tired of having to boot up my PC just to sync my iPod for two minutes. Thanks!!

Click here and follow the instructions.
(71663)

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Edit > Preferences > Store check Music under Automatic Downloads.
Open the iTunes Store from left hand column, then select Purchasedfrom the column on the right, click the Not In My Library button and select the tunes you want to download again.
That said, you seem to be under a misapprehension as to how iTunes works, or at least how it has worked in the past. It has, until recently, been up to you take care of your purchases once they have been downloaded. You had a one-time download which you were reminded to back up. With the recent change to this policy you can at least download your store purchases again, but having a personal backup of your iTunes store purchases, stuff purchased elsewhere and files ripped from your CDs will still be preferable to gathering all the stuff together again in the event of a disaster.
For a backup strategy see this User Tip.
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HT3281 I HAVE DOWNLOADED SONGS INTO ITUNES. WHEN I GO TO FILE THE SYNC IPOD IS NOT HIGHLIGHTED. I HAVE SYNC SONGS SEVERAL TIMES BEFORE

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I believe I have previously used this method to sync to my Ipod!

Will the media file play with Quicktime Player? If it will then it's an iTunes issue. If it won't then you need to delete the file and download it a second time.

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I'm not sure if it's taboo on these boards or not, but this is just a friendly "bump" to see if it might catch the eye of someone who has discovered a fix for this behavior.
I did discover a couple of suggestions in my research, neither of which proved helpful to me. The first was to disable the sync function for contacts with Outlook (no joy). The second was to delete the Sync Services folder (which I "temporarily" deleted, but still no joy).
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I moved all my music and photos to an external drive.
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can't figure out what's wrong... just got the ipod yesterday... i tried reinstalling itunes over again and restore ipod but still won't sunc.

Are you syncing photos as well? If yes, try to delete the photo cache, explained here: iTunes: Understanding the iPod Photo Cache folder

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I really could use some help, I have tried everything and don’t know what happened. I plugged my Nano iPod into my computer as I have always done since I received it as a gift for Christmas, to create a new playlist and sync it. When I plugged it into the computer all my music was gone on my iTunes, however it was still on my iPod. Since then, I have done all the upgrades, gone thru everything I can think of to find my music but can’t. I have purchased massive amounts of music and I’m afraid if I sync my iPod it will erase what I have and I have to start all over. I don’t know what happened to the music.
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Copying from iPod to Computer threads...
http://discussions.apple.com/thread.jspa?threadID=1534227&tstart=0
http://discussions.apple.com/thread.jspa?threadID=893334&tstart=0
http://discussions.apple.com/thread.jspa?messageID=797432&#797432
Also these useful internet articles...
http://www.ilounge.com/index.php/articles/comments/copying-music-from-ipod-to-co mputer/
http://www.engadget.com/2004/11/02/how-to-get-music-off-your-ipod/
http://playlistmag.com/secrets/2006/12/twowaystreet20/index.php
http://playlistmag.com/help/2005/01/2waystreet/
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ITunes telling me to repeatedly authorize account to sync ipod

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