I have just upgraded to SP1 on my Exchange 2010 installation and now a lot of my users are being prompted for a password when they open Outlook. It appears to happen in both Outlook 2007 and Outlook 2010. The odd thing is that if I close Outlook and reopen it might not prompt for the password and connect as normal. I did not have this problem before upgrading to SP1. I have tried changing to NTLM authentication on the security tab but that hasn't helped. I have also disabled Outlook Anywhere but the problem still occurs. I should mention that this is occurring within the LAN environment.

Hi Just a simple question, have you restarted the server after the SP1 have been applied? Give it a try If it doesn't help check with ExBPA and update the thread Are the clients connecting using MAPI/RPC?Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog

Now that I think about it I'm not sure I have restarted it. I originally thought that I did but it's possible I didn't I'll give that a shot. These are direct exchange connections. If the restart doesn't help I will run the ExBPA and let you know. Thanks.

I have restarted the Exchange server but unfortunately it had no effect. I have run ExBPA and nothing is jumping out at me as a problem. I will run another test but enable user permissions. That test takes a while so I'll have to report back on that one. Our clients are configured using a direct Exchange connection but autodiscover will enable Outlook Anywhere whenever it's unchecked. I have the boxes that ask to use http first instead of TCP/IP unchecked to make sure it uses a TCP/IP connection first.

I installed Fiddler 2 to see whether or not Outlook was making http calls and it turns out it is. It's making https calls to my owa site ao I guess it is still using Outlook Anywhere to connect. I'm still not sure why it would prompt for a password sometimes but not all. I tried enabling Windows Authentication on the owa virtual diectory in IIS but that didn't help either.

I have even more information now. When a client connects and does not get prompted it is connection directly to the exchange server. When they are connected it is always going through the OWA site. What would cause it to use the Ooutlook Anywhere connection inside the network? We're on a 1GB connection throughout.

Its failing over to Outlook Anywhere if it encounters network issues or failures. The prompting for passwords tells me you are using Basic authentication for Outlook Anywhere. You can change the auth to NTLM with the set-outlookanywhere command, however I would test this before making any changes. http://technet.microsoft.com/en-us/library/bb123545.aspx

Andy, I would love to use NTLM but it's my understanding that a Cisco ASA will not pass it through traffic which would be an issue for my mobile users. I need to find what is causing the connections to fail over to OA instead of TCP/IP. Everything was working fine until I installed SP1.

As Andy mentioned, the prompt password behaviour should be expected for basic authentication. To fix this issue, you should change the basic authentication to NTLM on the Outlook side. I also found one user who found the fix on the Exchange server. Under Autodiscover properties> Directory Security> Authentication Methods>?He checked "Integrated Windows Authentication". For more information, please refer to the link. http://office.microsoft.com/en-us/outlook-help/use-outlook-anywhere-to-connect-to-your-exchange-server-without-vpn-HP010102444.aspx Kevin

I am having this issue with Outlook (non cached) clients on my terminal server.

Kevin, The reason we use outlook anywhere is full outlook experience for remote clients. Those clients most of the time are not domain joined. With outlook anywhere enabled with basic authentication these clients can connect with outlook remotely. This is still working perfectly in Exchange 2010 Sp1. But since we impemented Sp1 our LAN clients (which are domain joined) are suddenly also being configured with outlook anywhere setting. When we uncheck outlook anywhere on the LAN outlook client all is working fine but autodiscover enables the checkmark again automatically. And yes, when we enable NTLM the LAN clients will autologon but our remote clients can no longer access through outlook anywhere. The domain joined LAN clients were not automatically enabled with outlook anywhere before Sp1. Marc

Hello Chris , do you have anny solution to your aoutlook pasowrd problem ? we in our company have same rouble and same reasone wha not want to use ntlm ?

Hi Marc If you change auth to NTLM with set-outlookanywhere, remote clients should still be able to access through outlook anywhere, even if they are not domain joined. If you enabled NTLM, did you also change auth methode on the remote clients from basic to NTLM? Regards PanoPano Boschung, PageUp AG