I am running two servers, Ex2007 on 2003R2, and Ex2010 on 2008R2. Since SP1, I have been working alot of kinks out, but still have some nagging authentication issues. People on the LAN on the 2007 server, keep getting prompted for credentials against the 2010 server (autodiscovery is now setup to 2010 server)..??? This is not impacting their connection, just annoying. I also have Win7 for my personal desktop, and Outlook 2010, and reside on the 2010 server, and I get prompted once each time I run outlook, even though outlook anywhere is not checked. Not sure if the two are related, but since Ex2010SP1, alot of my settings got changed. I was running require SSL with basic authentication over OWA on both servers. Any thoughts where my authentication methods are not restored properly? I checked IIS on 2010, and OWA and EWS require SSL.. OWA just has basic, while EWS also has Windows Authentication enabled. I am suspect of that. Thanks for any insight.

So, the issue happens on the windows 7 with outlook 2010, and the mailbox is on the exchange 2010 server Outlook anywhere isn’t enabled on the exchange 2010 server, and proxy setting button is unchecked on the problematic outlook, right? Please describe the exchange topology Please verify if the issue happen to all mailboxes on the exchange 2010 server Please run “Test Email AutoConfiguration” on problematic outlook client, and then check if the response is returned correctly Please refer to this article to check the authentication settings on the exchange 2010 serverJames Luo TechNet Subscriber Support (http://technet.microsoft.com/en-us/subscriptions/ms788697.aspx) If you have any feedback on our support, please contact tngfb@microsoft.com