ITunes will not copy certain songs to my iPhone - I'm "not authorized for it on this computer"

Hi. I get an error when I try to transfer certain songs from my computer to my iPhone. I get the following error, "(song name) was not copied to iPhone "____" because you are not authorized for it on this computer." For the particular songs for which this error comes up, I purchased them many years ago. I had them on my PC and transferred them to my iPhone just fine. I recently got rid of the PC and bought a Mac Mini (yay!) and copied my files over to the new computer. Then, I connected my iPhone to the Mini and synced it. Then, I noticed that there were some songs on my phone that I didn't want on it so I unchecked them in the Library on the Mini and chose the "sync only checked songs" option and synced again. Nothing changed. So, then I did an Autofill thinking that would make the selected songs on my Mini and matched the songs I wanted on my iPhone. That's when I noticed the songs missing on my iPhone (songs that I had selected on my Mini and wanted on the iPhone). I've never really been able to figure out how to work iTunes so I'm sure I've done something wrong. I can't decifer the error message so your help would be greatly appreciated. (I've authorized the Mini.)
Any ideas what the problem might be? Thanks in advance.

Hi there!
I've a very similar & the same problem but for me this has been happening ever since iTunes 7.1.5, so not exclusively since 7.2 was launched
In addition to the same problem you're having, iTunes will not sync any of my converted DVD movies and several video podcasts giving me the same error message you mentioned. If it try to play these video's out side of iTunes with QuickTime, I get 'Error -36: An I/O Error' warning and thats it, but I can play with any other media player including the dreaded Windows Media Player! If I copy these files on to a separate HHD, Flash Stick or on to another PC (i.e. so they’re played from not in the iTunes folder in my documents) they all work fine and oddly also with QuickTime, so I'm happy the files are not corrupt. I'm afraid to attempt to play any remaining video's that I managed to sync sometime before this problem in iTunes because when I do, its then that I can never use it again and it gets removed from my iPod!
I can't find anything on this problem anywhere, and I don't know where to go to get help from Apple not that I’m sure they’d be too helpful?
Does anyone have any suggestions?
Thanks
Regards
Jaime
PS: Running Vista Enterprise and I have the MS Vista Patch loaded despite never having a problem either burning CDs or ejecting my iPod?
White 5G - boot ver 1.2.1 Windows Vista Intel Duo 2.2Ghz, 1.5GB Ram, 2x 350GB Disks - Encoding AAC 256bps via iTunes

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Check your source hard drive for errors, right-click on the drive holding the library, click Properties, tools, check for errors, scan for and attempt recovery of bad sectors...
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Repair Security Permissions
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This helped meRe: not copied to iPad because you are not authorized for it on this computer
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Hello LeaMinovitch,
Thanks for using Apple Support Communities.
For more information on this, take a look at:
iTunes Store: Authorize or deauthorize your Mac or PC
http://support.apple.com/kb/ht1420
To authorize a computer, follow these steps:
Open iTunes.
Choose Store > Authorize This Computer from the menu bar.
You may need to show the menu bar to see this option in Windows. In earlier versions of iTunes, you can access this option from the Advanced menu.
Enter your Apple ID and click Authorize.
If your Apple ID uses an expired MobileMe account, you can still authorize your computer.
In some cases, iTunes may ask you to authorize the computer again. iTunes should use the same authorization as before if the computer is in your list of authorized computers.
Learn what to do if iTunes repeatedly asks you to authorize when you try to play your content.
Best of luck,
Mario

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ITunes will not copy certain songs to my iPhone - I'm "not authorized for it on this computer"

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