I have a sbs 2008 server running exchange 2007 and outlook 2007 on the workstations. I was able to configure autodiscover a couple months ago and everything was working fine. I did a reboot on the server last night and now whenever someone opens their outlook it prompts for a password for remote.domainname.com and autodiscover.domainname.com. Now our primary owa address is the remote.domainname.com. I just created a cname for autodiscover to forward to remote.domainname.com.
So once it asks for username and password i type in the users domain/username and password. The prompt continues to come back. If i cancel out of the prompts outlook connects fine. It then just pops up a little bubble every so often saying you need to type in your password.
I also ran the test email autoconfiguration wizard and it says that it can't determin the settings. Everything was working fine until the reboot. what could have happen?