Tiger - Mail Attachment Issues -

I am sitting next to a friend, he is running a Macbook with Tiger installed on it. In the Apple mail application he is having problems with attachments.
If you send one of any file to him PDF, DOC, TXT... The file will open just fine.
If you send multiple files of any kind ONLY the first file will open up. The others report;
Error couldnt open file
By that I mean, Send 5 PDF files, only the first of the 5 files attached is viewable the remainder do not work. Error code above.
This has been going on for over a YEAR...
I have not gone into settings yet but I am pretty certain it is an AOL email addy.
Thanks,
Richard Alan

Not certain, but this can fix myriad Mail problems...
Safe Boot from the HD, (holding Shift key down at bootup), it will try to repair your Disk Directory while the spinning radian is happening, so let it go, run Disk Utility in Applications>Utilities, then highlight your drive, click on Repair Permissions, then move these folder & file to the Desktop.
Move this Folder to the Desktop...
/Users/YourUserName/Library/Caches/Mail/
Move this file to the Desktop...
/Users/YourUserName/Library/Mail/Envelope Index
Reboot.
If that doesn't do it and you can afford to redo all your Rules, try these & reboot...
/Users/YourUserName/Library/Mail/MessageRules.plist
/Users/YourUserName/Library/Mail/MessageRules.plist.backup

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