TS1389 older purchases from iTunes keep on prompting me to authorise and still don't play.

i'm having trouble with older purchases from itunes, now that i'm transferring them from a pc to a mac. Tracks and albums brought within the last two years are fine, but anything older as me to authorise to computer each time try to play the track.

Hello makray,
I was looking into reasons why iTunes would keep prompting you to authorize items and still not play them, and found a great little article. It is named iTunes repeatedly prompts to authorize computer to play iTunes Store purchases found here: http://support.apple.com/kb/TS1389.
This is the overview of things to try but each one has its own set of instructions.
Authorize your purchases from an administrator account
Authorize using the correct account name
Turn Off User Account Controls (Windows Vista and Windows 7 Only)
Remove the SC Info folder
All the very best,
Sterling

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Hey there Eb69,
It sounds like you have some purchses that seem to have been interupted when they were downloading. I would start by using this info to resume the downloads:
If your download was interrupted using your iPhone, iPad, or iPod touch
From the Home screen, tap the iTunes app.
For iPhone or iPod touch, tap More > Downloads. For iPad, tap Downloads.
Enter your account name and password if prompted.
Tap the blue download arrow to resume.
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From: iTunes: How to resume interrupted iTunes Store downloads
http://support.apple.com/kb/ht1725
Thank you for using Apple Support Communities.
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For customer service issues, go here...
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Deauthorize your Mac, then authorize it again.
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frank_o_s wrote:
My kid`s been using my apple ID/account for years, but now that he`s older it`s time he got his own. Is there any way to either make a twin account so he doesn`t lose all his purchases from iTunes/AppStore or does he have to start from scratch? They payment can still be from my card/account, that`s not the problem, but facetime, imessage etc. is a available on both mine and his apple products (I know you can check what email/phone number we can be reached at, but it`s just a click and he see my messages and I his). It`s the privacy problem that is the most important.
He needs to have his own account, the sooner the better.
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Hi Poonam26c,
If you do not have a local copy of a song which you have purchased (i.e. it is available via iTunes in the Cloud), you may need to redownload it before you can transfer it to your device. You may find the following article helpful:
Apple Support: Downloading past purchases from the iTunes Store, App Store, and iBooks Store
http://support.apple.com/kb/HT2519
Regards,
- Brenden

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Why do I keep getting unable to purchase from iTunes Store try again later ?

Hi Nanas12,
Thanks for visiting Apple Support Communities.
If you continue to see an "unable to purchase" message on the iTunes Store, I recommend the troubleshooting steps in this article:
Can't connect to the iTunes Store
http://support.apple.com/kb/ts1368
Cheers,
Jeremy

TS1389 older purchases from iTunes keep on prompting me to authorise and still don't play.

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