Mac Mail Freezes when attaching files

Ever since my upgrade to snow leopard, my mac mail does 2 things. 1, it keeps asking for my name and password, and I have already cleared out my keychain, re input all my information, and it keeps doing that. does it about once a day.
but my more detrimental problem is that my mail will freeze the entire freaking system if I try to attach a file! Used to, I didn't have this issue, and it's only doing it on my imac. I have snow leopard on my macbook and it works just fine when I attach a file. On top of that, it's doing it when I attach a mp3.
I am not sure what to try here. But it doesn't just freeze up mail, but the entire mac. I mean, I can't even do a Command Option Esc to close mail, because it locks up the entire freaking system. I don't know what to try here.

I would start by setting up another user account, set up mail.app with your info on that account and see what happens there. If everything works fine there, I would (in the normal account) export all messages etc in mail.app (and make sure you have backup), delete (or rather rename) all mail prefs etc and set the mail.app up again and then (when everything hopefully works) import all old messages.
Btw, I assume that you have repaired permissions on the disk and that "cleared out the keychain" also included doing a first aid repair for the keychain.

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    Hi Lessa,
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    "Try Disk Utility
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    2. When your computer finishes starting up from the disc, choose Disk Utility from the Installer menu. (In Mac OS X 10.4 or later, you must select your language first.)
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    3. Click the First Aid tab.
    4. Click the disclosure triangle to the left of the hard drive icon to display the names of your hard disk volumes and partitions.
    5. Select your Mac OS X volume.
    6. Click Repair. Disk Utility checks and repairs the disk."
    http://docs.info.apple.com/article.html?artnum=106214
    Then Safe Boot from the HD, (holding Shift key down at bootup), run Disk Utility in Applications>Utilities, then highlight your drive, click on Repair Permissions, reboot when it finishes.
    If you still have the same problem...
    Quit Mail.
    Then in your Home folder. open Library folder, open Caches folder in that, look for the Mail, and drag it to the Desktop.Move Envelope Index to the Desktop in...
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    This forum is for the MacBook Pro hardware.  You might get a better answer in the Safari forum, but you will have to provide more information there. 
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  • Safari Freezes when attaching files

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    Verify/repair the startup disk (not just permissions), as described here:
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  • Mail freezes while attaching file in Maverick

    Problem: When I attempt to attach a file in Mail it freezes and is not reponsive. It requires me to force quit the program.
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    Thanks for the reply.  I'm sorry, my question wasn't clear. I was actually speakiing of web based email, like Yahoo.
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  • Apple Mail Crashes when attaching file

    Hi,
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    figured out my issue finally....and it was also the reason that my computer was running hot....i didnt have a certain folder permissions set to me with read and write....which ultimately messed with my keychain....this is a 2 min fix....  check out on this thread the post by james hunkins....
    https://discussions.apple.com/thread/3396579?start=30&tstart=0
    happy i found this as has put multiple issues to rest for me hope it helps you out too

  • Mail freezes when attaching PDF from Acrobate

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    Mail sometimes gives me an error (don't have it exactly, sorry)
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  • Safari 5.0 freezes after attaching files in Yahoo Mail

    Since upgrading to Safari 5, I cannot use Yahoo mail after attaching a file to a message. The program acts like there is a dialog box open and it is waiting for a choice to be made, but there is no dialog box.

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