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I support many Macs that connect to an SMB share on a Windows Server 2008 R2 box. Occasionally I find that the Mac will try to connect and fail. The connection process will skip asking for credentials and there are none stored in keychain's password section. The server logs will show that the user tried to authenticate with invalid credentials. There are also no lingering connections from the server's point of view.

The work around that I've found is to use an invalid username or a username that isn't the user's in the connection string for SMB so smb://domain;user@server/share instead of 'smb://server/share' this will force it to use the username I specified which the client doesn't have anything stored for. So it will then pop up the login window where the user changes the username to the correct one and user her password to connect happily.

Specific computer in question: 15" MBP running Snow Leopard (10.6.7 or 10.6.8)

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Anything in the console log for the Mac in question? (viewable via the application named Console) –  databyte Nov 16 '11 at 23:28
    
We have a few clients with a similar setup (2003 and 2008) and I've seen the same thing with every version of OSX. It seems to occur more often with the older releases but we've seen situations where recent releases will suddenly stop being able to log in using AD credentials (where others on the same network are able to). We change things and change things and suddenly it starts working - but we have yet to work out why or see anything consistent. If you find a solution I'd like to know. –  Ian Murphy Nov 17 '11 at 13:55
    
A reboot helped with the specific issue but I'm going to pull console logs next time I see this. –  Tawm Nov 30 '11 at 0:38
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