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I have several user who travel and connect to our network using Citrix VPN. Once they are connected they can connect to our servers..etc. but when opening up Outlook they are greeted with a login window. No combination of usernames will allow Outlook to connect to the Exchange Server. If the user is in the office, the connect works just fine. Note: This is only a handful of users out of hundreds. I even tried a brand new machine but the issue still remains for these people. Any thoughts?

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  • Does the Connection Status window of Outlook (accessible by CTRL+Right Clicking the Outlook icon in the systray) show any connections? If so, what? In particular, any connections under the type "Directory" - what does it say under in "Conn" column? Its possible that the Citrix VPN is breaking Kerberos trust between the client and the server.
    – Ashley
    Nov 20, 2012 at 21:12

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  • What version of Exchange are you using ?
  • Are these domain joined workstations connecting over VPN ?

2 suggestions.

  • Try rpcping utility from the workstation to the server over VPN.

    RPCPing.exe -t ncacn_http -o RpcProxy=fqdn.yourdomain.com -P "testuser,yourdomain,testpassword" -I "testuser,yourdomain,testpassword" -H 1 -u 10 -a connect -F 3 -E -v -3 -R none -q

  • More details on RPCPing here - http://support.microsoft.com/kb/831051

  • For non domain joined workstations, you can specify additional credentials.
  • For Windows7 and Up, Go to Control Panel> User Accounts > Manage your credential, Add a Windows Credential. That should take care of the login window.
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