Hi First I have 2 Exchange 2010 SP2 mailbox servers and one Exchange 2010 SP2 CAS/Hub server. My clients are using Outlook 2007 and 2010 autodiscover, outlook anywhere are enabled and many are connecting to Exchange via VPN after work hours I have a problem with some of my VPN clients (only 4 or 5 on 488 exchange users) when they are connected through VPN Outlook is asking for their password every 4-5 minutes. When they enter their password it is working until Outlook re-ask for credentials. Also for those users Outlook Anywhere is not working at all. When they are connected to the lan directly they don’t have any issue with Outlook. They all using Outlook 2007 SP2 I tried to recreate their profile Do you have any idea for this strange problem? Thanks

Hi, Since the problem only happen to a few users, it should be caused by the client issues. Step 1. Please clear the domain credential cache: ====================== a. On the user's machine, click start button->Run, type: control userpasswords2 b. In Advanced tab, click Manage Password, delete the domain credential cache. Step 2: ===================== a. Open outlook E-mail Account setting page, click "more settings" b. In Security tab, make sure the "Always prompt for logon credentials" is unchecked. The logon network security is set to "Negotiate Authentication". If the issue persists, please test the problem in a new local windows profile (create a new windows account on the client's machine).Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread. Thanks Gen Lin-MSFT

Hi, How troubleshoot is going on?Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread. Thanks Gen Lin-MSFT