I believe this is a problem with the VPN/RDP settings or possibly the credential manager / RDP client combination. We have Windows VPN configurations to assist each client. The VPNs themselves appear to function normally with a Windows XP configuration; unchecking the "Use default gateway on remote network" under the TCP/IP protocol was the only change required. When using any Windows 7 Pro machine, we unchecked the same setting, left all others as defaults, and now every time a VPN to a client is connected and an RDP connection is initiated to the workstation we're working on, our Outlook disconnects from the Exchange server with a "need password". It's a little intermittent and I'm having a devil of a time figuring out exactly what steps are needed to reproduce the issue consistently. I'm leaning toward a routing issue as the password prompt asks for the password to "remote.domain.name", not to the internal exchange system. Ironically, if I just close the repeated popups, the Outlook-Exchange connectivity still appears to work and messages still arrive into my cached Outlook inbox even though "need password" is displayed instead of "connected to Microsoft Exchange". Note: I've compared the settings with my previous WinXP configuration, unchecked the IP6 protocol in the VPN properties, disabled UAC and Firewall. In Outlook 2007 I'm running a cached mailbox, and in the Account Settings I've unchecked the Outlook Anywhere HTTP checkbox. After ignoring the password prompt an event is created in the Administrative Events log: "The password stored in Credential Manager is invalid. This might be caused by the user changing the password from this computer or a different computer. To resolve this error, open Credential Manager in Control Panel, and reenter the password for the credential MYLOCALDOMAIN\admin" Now, this is the weird part - I'm logged into my machine using my local domain's login. I've connected the VPN and logged into my client's domain as Admin. The error above references MY DOMAIN\ADMIN. Where the devil is that coming from? It seems to have combined the fact that I'm logged into my domain with the fact that the login for the RDP machine is using Admin.