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Since I asked this question we've moved off 2003 and are using User Profile Disks with 2012r2 (they were introduced with 2012): The simpler way is user profile disks. User profile disks store user and application data on a single virtual disk that is dedicated to one user’s profile [...] User profile disks provide an easy way to store the user settings ...


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Please re-install the terminal Services, but before that please change ' Restrict each user to one session ' to 'No' and than change it to 'yes' and even if your issue doesn't resolve than only re-install Terminal Services.


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This is a common issue with Outlook 2007 and later (I suppose you use one of these versions, because Outlook 2003 doesn't have these problems). It requires a default gateway to be set. Try the registry fix or use the "Fix it" from MS, I'd say.



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