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Helpful answers
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Feb 28, 2016 12:35 PM in response to ab1989by Drew Reece,Select the songs in iTunes & use 'File > Get info'.
Examine the 'Summary' tab to see what kind of file they are and if they are 'protected' or tied to another Apple ID etc.
Post back what you find, also compare them to the files that burn.
I suspect you may have files that cannot be converted.
Please confirm what type of CD you are burning - is it 'Audio', 'MP3' or 'Data CD'?
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Feb 28, 2016 12:42 PM in response to Drew Reeceby ab1989,Looks like you're on to something!
Burning an audio CD. Files that aren't burning are protected and were purchased under our old Apple ID. We haven't used the old ID in at least 10 years. This has never been a problem until now.
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Feb 28, 2016 1:23 PM in response to ab1989by Drew Reece,★HelpfulI'm not sure what you can do to resolve this besides the obvious – repurchase under the current Apple ID.
The files need to be authorised to play so I guess your Mac still has that iTunes authorisation from the old account. There are limits on the number of times you can burn the same playlist to a CD when using Apples 'FairPlay DRM'. The idea was to stop you making dozens of copies of the same album, I think it was 7 burns per playlist. A new playlist should use a new counter.
If you can manage to burn them you can rip back into iTunes, it is a legitimate way to remove the DRM & Apple supported it. If you have an older disk with these tracks you can extract them from that.
Old Apple ID's are a pain, there is no way to transfer the purchased items to another account.
Dig up older articles for the background…
http://inside-apple.blogspot.co.uk/2006/09/itunes-and-7-burn-limit_15.html
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Feb 28, 2016 1:23 PM in response to Drew Reeceby ab1989,★HelpfulThanks very much, Drew! Not happy to hear songs purchased under the old ID aren't transferable... should only have to buy once! You've provided solid tips on how to proceed and I'm very grateful!
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Feb 28, 2016 1:40 PM in response to ab1989by Drew Reece,ab1989 wrote:
Not happy to hear songs purchased under the old ID aren't transferable... should only have to buy once!
I'm not sure anyone but the music labels are happy with this situation
Newer music files from the store don't have the DRM (they should be 'iTunes Plus'), so they should be less susceptible to this issue, only iTunes Match & Apple Music downloads have the DRM (it allows the subscription to be revoked/ cancelled).
If the old ID is still active you may be able to convert to iTunes plus format…
About iTunes Plus - Apple Support
See if a password reset on that ID gets you anywhere (check all your spam folders incase it is re-routed).
It may be more cost effective to repurchase